[DEF 14A] CANTALOUPE, INC. Definitive Proxy Statement

Rhea-AI Filing Summary

Cantaloupe, Inc. is asking shareholders to vote at its annual meeting on director elections, approval of executive compensation and ratification of its independent auditor while describing recent operational progress and a pending merger. The company entered a Merger Agreement with 365 in June 2025, expected to close in the first half of calendar 2026 subject to HSR clearance and other closing conditions. Management highlights product launches (AdVantage digital media, Smart Store, Go Micro kiosk, Engage Pulse card readers), a UK/Europe acquisition (SB Software), new sports and entertainment clients, and a financing program (Cantaloupe Capital) with Fundbox. The company amended and expanded credit facilities to increase borrowing capacity and paid transaction bonuses tied to the Merger. The proxy discloses governance items (board independence, proxy access), director and named executive officer compensation practices and peer-group benchmarking, auditor fees and the Audit and Risk Committees recommendation to retain Deloitte for fiscal 2026. The filing also lists material risks, including the possibility the Merger may not close and operational, regulatory, and market risks that could affect results.

Insights

M&A Strategist

TL;DR: A announced merger with a first-half 2026 close window is the dominant near-term material item.

The filing confirms a Merger Agreement with 365 signed in June 2025 and an expected closing in the first half of calendar 2026, conditional on HSR clearance and customary closing conditions. That transaction, if completed, will supersede standalone execution and is central to shareholder value realization during the stated timeframe.

The principal near-term dependencies are regulatory clearance under the HSR Act and satisfaction or waiver of closing conditions; litigation, costs related to the transaction, or failure to obtain approvals are specifically disclosed risks and could delay or prevent closing within the projected window.

Corporate Finance & Liquidity Expert

TL;DR: Expanded credit capacity and transaction bonuses signal financing flexibility tied to the Merger.

The company discloses amendments that increased total borrowing capacity to support growth initiatives and paid transaction bonuses ($200,000 and $100,000) to two executives in connection with the Merger Agreement. These items affect near-term cash flows and compensation expense.

Key items to watch before the merger close include the size and terms of the amended credit facilities, any covenant compliance issues, and incremental costs tied to the merger proxy and due diligence disclosed as audit-related fees during fiscal 2025.

Compensation Governance Specialist

TL;DR: Compensation changes emphasize pay-for-performance alignment and retention ahead of the Merger.

The Compensation Committee reports ongoing restructuring of executive pay since fiscal 2022, tying material compensation to performance goals and equity incentives and using a 16-company peer group for benchmarking. The filing details annual bonuses, equity grant practices, and disclosure of transaction-related cash bonuses paid in connection with the Merger.

Watchable items include the disclosed resignation of an NEO effective October 7, 2025, the structure of equity vesting provisions for NEOs, and any shareholder feedback from the say-on-pay vote that could influence future compensation design.

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UNITED STATES
SECURITIES AND EXCHANGE COMMISSION
Washington, D.C. 20549

SCHEDULE 14A

Proxy Statement Pursuant to Section 14(a) of the
Securities Exchange Act of 1934

☑ Filed by the Registrant ☐ Filed by a party other than the Registrant

CHECK THE APPROPRIATE BOX:
☐			Preliminary Proxy Statement
☐			Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2))
☑			Definitive Proxy Statement
☐			Definitive Additional Materials
☐			Soliciting Material under §240.14a-12

Cantaloupe, Inc.

(Name of Registrant as Specified In Its Charter)
(Name of Person(s) Filing Proxy Statement, if other than the Registrant)

PAYMENT OF FILING FEE (CHECK ALL BOXES THAT APPLY):
☑			No fee required
☐			Fee paid previously with preliminary materials
☐			Fee computed on table in exhibit required by Item 25(b) per Exchange Act Rules 14a-6(i)(1) and 0-11

Vision

To be the global technology leader powering self-service commerce.

A Message from our CEO and
Non-Executive Chair

			October 10, 2025 Dear Shareholders, You are cordially invited to attend the 2026 Annual Meeting of Shareholders (the “Annual Meeting”) of Cantaloupe, Inc. (“Cantaloupe” or the “Company”) to be held online in a virtual format at 11:00 a.m., ET, on Wednesday, November 19, 2025, via live webcast at www.virtualshareholdermeeting.com/CTLP2026. On behalf of the board and all of our employees, we thank you for your support of the Company and for your continued investment in Cantaloupe. Fiscal year 2025 was marked by strong financial performance, driven by disciplined execution. We achieved total revenue of $303 million, a 13% increase year-over-year, led by a 15% increase in transaction fees and an 11% increase in subscription fees. We expanded our customer base by 11% to 34,896 active customers and grew our active devices by 5% to 1.28 million, reflecting ongoing demand for our platform. As you know, in June 2025, we entered into a merger agreement (the "Merger Agreement") with 365 Retail Markets, LLC (“365”)(the “Merger”). The Merger was approved by our shareholders in September 2025, but is subject to regulatory clearances, including under the Hart-Scott-Rodino Antitrust Improvements Act of 1976, as amended (the “HSR Act”). Subject to those clearances and the satisfaction or waiver of the other closing conditions in the Merger Agreement, the Merger is currently expected to close in the first half of calendar year 2026. Until then, we remain an independent public company and will hold our regular annual meeting. The matters to be voted on at the annual meeting do not include the Merger. Aside from the Merger, operationally, we continued strengthening our business through innovation and expansion. We acquired SB Software to enhance our presence in the U.K. and Europe, launched products including Smart Store and the Go Micro kiosk, and expanded our presence at entertainment venues with partners like the San Jose Earthquakes and Carnival Cruise Line. Looking ahead, as we work toward completing the Merger, we remain focused on maintaining our commitment to operational excellence and innovation. We are dedicated to ensuring a smooth transition for all stakeholders and continuing to deliver high-quality service and performance until the transaction closes. Your vote is very important to us. If you are unable to attend the annual meeting, please vote in advance of the meeting online, by mail or by telephone to ensure your shares are represented. Thank you for your continued support and investment in Cantaloupe. We look forward to meeting with you on November 19, 2025. Sincerely,
			Ravi Venkatesan Chief Executive Officer			Douglas G. Bergeron Independent, Non-Executive Chair

2026 Proxy Statement 1

Table of Contents

A Message from our CEO and Non-Executive Chair						1
Notice of 2026 Annual Meeting of Shareholders to be Held Wednesday, November 19, 2025						3
Fiscal Year 2025 Performance Highlights						5
Proxy Summary						7
			Proposal 1 – Election of Directors			14
Nominees for Election as Director						15
Nomination Process						24
Director Majority Voting Policy						26
Corporate Governance						27
Board Leadership Structure						27
Board Committees						28
Board Operations						33
Board’s Role and Oversight Responsibilities						34
Other Governance Policies and Practices						37
Compensation of Non-Employee Directors						39
Director Compensation Program						39
Stock Ownership Guidelines						40
Fiscal Year 2025 Director Compensation						40
Certain Information About Management						41
Executive Officers						41
			Proposal 2 – Advisory Vote to Approve Compensation of Named Executive Officers			44
Compensation Discussion & Analysis						45
Our Named Executive Officers						45
CD&A At-A-Glance						47
Our Compensation Philosophy						49
Compensation Process						50
Fiscal Year 2025 Executive Compensation						51
Executive Officer Employment Arrangements						58
Compensation Policies and Practices						60
Compensation Committee Report						64

Executive Compensation Tables and Related Disclosures						62
Summary Compensation Table						62
Grants of Plan-Based Awards						63
Outstanding Equity Awards at Fiscal Year-End						64
Option Exercises and Stock Vested						65
Potential Payments Upon Termination or Change of Control						65
CEO Pay Ratio Disclosure						67
Pay Versus Performance						68
Policies and Practices for Granting Certain Equity Awards						72
			Proposal 3 – Ratification of Appointment of Independent Registered Public Accountants			73
Engagement of Deloitte						73
Audit Matters						74
Principal Accountant Fees and Services						74
Audit and Risk Committee Pre-Approval Policy						75
Report of The Audit and Risk Committee						75
Stock Ownership Information						76
Security Ownership of Certain Beneficial Owners and Management						76
Delinquent Section 16(a) Reports						78
Questions and Answers About the Proxy Materials and Annual Meeting						79
Other Information About the Annual Meeting						84
Expenses of Solicitation						84
Householding						84
2027 Shareholder Proposals and Director Nominations						85
Other Matters						86
Special Note Regarding Forward-Looking Statements						87
Appendix A - GAAP to Non-GAAP Reconciliation of Adjusted EBITDA						89

2 2026 Proxy Statement

Notice of 2026 Annual Meeting of Shareholders to be Held Wednesday, November 19, 2025

Date and Time 11:00 a.m., ET, on Wednesday, November 19, 2025			Virtual Annual Meeting Site www.virtualshareholdermeeting.com/CTLP2026. There will be no physical meeting.			Who Can Vote Holders of our Common Stock and Preferred Stock as of September 25, 2025 (the “Record Date”)

Matters to be Voted On

Proposals						Board Vote Recommendation			For Further Details
1			Election of nine directors nominated by the Company’s Board of Directors to serve until the next Annual Meeting of Shareholders.			“FOR” each director nominee			Page 15
2			Approval, on an advisory basis, of the compensation of the Company’s named executive officers.			“FOR”			Page 47
3			Ratification of the appointment of Deloitte & Touche LLP (“Deloitte”) as the Company’s independent registered public accountants for the fiscal year ending June 30, 2026.			“FOR”			Page 77
Any other business as may properly come before the meeting or any adjournment of the meeting.

Participating in the Meeting

You may vote during the Annual Meeting by visiting www.virtualshareholdermeeting.com/CTLP2026. To participate in the Annual Meeting, you must have your sixteen-digit control number located on your notice, on your proxy card or on the instructions that accompanied your proxy materials.

Date of Mailing

We will commence mailing the notice of Internet availability of proxy materials, or a proxy statement, proxy card and Annual Report on Form 10-K, to shareholders on October 10, 2025.

By Order of the Board of Directors,

Ravi Venkatesan
CEO
October 10, 2025

2026 Proxy Statement 3

Notice of 2026 Annual Meeting of Shareholders to be Held Wednesday, November 19, 2025

How to Vote

Internet Before the meeting: www.proxyvote.com or scan the QR code located on the proxy card During the meeting: virtualshareholdermeeting.com/CTLP2026			Phone 1-800-690-6903			Mail sign, date and mail your proxy card in the envelope provided

Important Notice regarding the availability of proxy materials: the proxy statement and form of proxy card are available at: www.proxyvote.com

4 2026 Proxy Statement

Fiscal Year 2025 Performance Highlights
Overview

Cantaloupe has a combination of subscription, transaction, and equipment revenues.

SUBSCRIPTION

TRANSACTION

EQUIPMENT

Software: Subscription for access to SEED software solution suite and digital services fees

Payments: fees associated with transaction processing

Equipment purchases: one time purchase fee

$263.1 million

$39.4 million

(87% of Fiscal Year 2025 revenue)

(13% of Fiscal Year 2025 revenue)

A scalable, modular platform to support businesses of all sizes.

Strategy

Growth within Existing Customers

Adjacent Vertical Expansion

Accelerating Subscription Revenues

International Expansion

Strategic M&A

2026 Proxy Statement 5

Fiscal 2025 Performance Highlights

Business and Financial Highlights

Active Customers(1) 34,896

Active Customer Growth (YoY) 11%

# of Transactions 1.2B

Dollar Volume of Transactions $3.4B

Active Devices(2) 1.28M

Recurring Revenue(3) 87%

Dollar Volume of Transactions Growth (YoY) 13%

(1)We define Active Customer as all customers with at least one active device.

(2)We define Active Devices as devices that have communicated with us or have had a transaction in the last twelve months. Included in the number of Active Devices are devices that communicate through other devices that communicate or transact with us.

(3)We define Recurring Revenue as the combination of our subscription and transaction revenue.

Operational Highlights

•We entered into a Merger Agreement with 365 in June 2025, with the transaction expected to close in the first half of calendar 2026, subject to regulatory clearance under the HSR Act and the satisfaction or waiver of the other closing conditions in the Merger Agreement;

•We launched the AdVantage digital media program in October 2024, enabling brands to engage with consumers through digital advertising on our POS touchscreen devices across the U.S. and Canada;

•We introduced Smart Store, an advanced self-service retail solution designed to address labor shortages, theft, and shrinkage, while delivering a seamless consumer experience;

•We expanded our presence in the sports and entertainment sector by signing the San Jose Earthquakes as a client for our POS technology solution and premium suites management system at their stadium;

•We launched Engage Pulse card readers for the arcade and amusement industry, offering a ladder pricing interface to maximize revenue potential and deliver a seamless payment experience for operators and consumers;

•We collaborated with Fundbox to launch Cantaloupe Capital, providing small businesses with streamlined access to capital for equipment investments and flexible cash flow solutions; and

•We enhanced financial flexibility by amending and expanding our credit facilities, increasing total borrowing capacity to support future growth initiatives.

6 2026 Proxy Statement

Proxy Summary

This summary highlights selected information in this proxy statement. Please review the entire proxy statement and our Annual Report for the year ended June 30, 2025, before voting your shares.

Annual Meeting Information

Date and Time November 19, 2025 at 11:00 a.m., ET			Virtual Meeting Site www.virtualshareholdermeeting.com/CTLP2026			Record Date September 25, 2025

How to Vote

Internet Before the meeting: www.proxyvote.com or scan the QR code located on the proxy card During the meeting: virtualshareholdermeeting.com/CTLP2026			Phone 1-800-690-6903			Mail sign, date and mail your proxy card in the envelope provided

7 2026 Proxy Statement

Proxy Summary

Proposal 1 Election of Directors
The Board recommends a vote “FOR” each director nominee.			See page 15

Director Nominees

Director			Occupation			Age			Director Since			Independence			Other Public Directorships						Committee Memberships
																					A			C			NCG			F
			Douglas G. Bergeron Former CEO, VeriFone (2001-2013) Chairman of the Board			64			2020						—
			Lisa P. Baird President and CEO, NextUp			64			2020						1
			Ian Harris Chief Financial Officer, Talkspace, Inc.			36			2022						—
			Jacob Lamm Founder & Independent Consultant, Enterik Advisory LLC			60			2020						—
			Michael K. Passilla CEO, Posillipo Ventures, Inc.			58			2020						1
			Ellen Richey Former Vice Chair of Risk and Public Policy, Visa Inc.			76			2020						1
			Anne M. Smalling President & Managing Partner, HM International, LLC			60			2020						—
			Ravi Venkatesan CEO, Cantaloupe, Inc.			49			2022						—
			Shannon S. Warren Owner & Principal, SSW Consulting LLC			56			2020						—

A

Audit and Risk Committee

NCG

Nominating and Corporate Governance Committee

Chair

C

Compensation Committee

F

Finance Committee

Member

8 2026 Proxy Statement

Proxy Summary

Director Nominee Demographics

2026 Proxy Statement 9

Director Qualifications

The Board annually reviews directors’ skills and expertise to ensure the Board represents a diverse skill set oriented to the historical and emerging needs of the business. The Board has identified the following key qualifications and experience that are important to be represented on the Board as a whole.

Risk Management & Compliance

Leadership & Senior Management

Mergers & Acquisitions

Accounting & Finance

Strategic Planning

Technology & Cybersecurity

Payments Industry

2026 Proxy Statement 10

Proxy Summary

Corporate Governance Highlights

Board Structure & Independence   Independent, non-Executive Chair of the Board   Eight out of nine directors are independent   Diverse perspectives and experiences   Independent Committee Chairs   Separation of CEO and Chair roles   Annual election of directors

Corporate Governance   Annual board and committee self-evaluations   Independent members of the Board meet regularly in executive sessions   Orientation and education for new directors   Over-boarding restrictions

Compensation   Annual approval of executive compensation   Prohibits our employees, officers, and directors from engaging in any hedging or similar transactions with respect to the Company’s securities   Significant stock ownership guidelines   No Excise Tax Gross-Up Provisions   Comprehensive Nasdaq-compliant clawback policy

Shareholder Rights   Majority voting for directors in uncontested elections with mandatory director resignation policy   Proxy Access   Shareholders can recommend director candidates   20% threshold for shareholders able to call a special meeting

2026 Proxy Statement 11

Proxy Summary

Proposal 2 Advisory Vote to Approve Compensation of Named Executive Officers
The Board recommends a vote “FOR” this proposal.			See page 47

Elements of Compensation

Base Salary

Key Characteristics

•Fixed compensation component payable in cash. Reviewed annually and adjusted when appropriate.

Why We Pay this Element

•Provide a base level of competitive cash compensation for executive talent.

How We Determine

•Experience, job scope, and individual performance.

•Market and peer data.

Annual Bonus

Key Characteristics

•Variable compensation component payable in cash based on performance as compared to Company and/or individual performance goals.

Why We Pay this Element

•Motivate and reward executives for performance on key operational, financial, and personal measures during the year.

How We Determine

•Organizational and/or individual performance. Discretionary bonuses are based on various factors, including past performance. We also review market and peer data in making bonus determinations.

•2025 Financial Goals: Revenue, Adjusted EBITDA, Monthly Recurring Revenue Growth.

Long-Term Incentive (LTI)

•Compensation Committee is focused on emphasizing equity as part of NEO compensation mix.

•Equity awards to NEOs primarily reflect initial awards in connection with hires and promotions, as opposed to awards granted under a general annual program.

•Substantially all of CEO’s equity grants are performance-based.

•Outstanding Performance-Based Options Goals: Share Price.

12 2026 Proxy Statement

Compensation Highlights

Our compensation program for our executive officers features many commonly used “best practices” including:

What We Do						What We Don’t Do
Pay-for-performance - We seek to tie a significant amount of executive compensation to the achievement of performance goals and as equity-based awards to link our executives’ long-term incentives with our shareholders’ interests.   Stock ownership guidelines - We have significant ownership guidelines. Our Chief Executive Officer is required to hold Common Stock with a value equal to a multiple of three times base salary and our Chief Financial Officer and other executive officers are required to hold Common Stock with a value equal to base salary (in each case subject to applicable grace periods for new executive officers).   Clawback Policy - A clawback policy that complies with Section 10D of the Exchange Act and Nasdaq listing standards, which provides for the recovery of incentive compensation from the Company’s current and former Section 16 officers in certain situations.						No Excise Tax Gross-Up Provisions - Our NEOs are not provided with any excise tax gross-up provisions with respect to payments contingent upon a change of control.    Limited perquisites for our executives - Perquisites are not a significant portion of our executive officers’ compensation, and generally consist of health, welfare, and retirement benefits broadly available to our employees.    No repricing of underwater options - Our equity incentive plans do not permit repricing or the exchange of underwater stock options without shareholder approval.

Proposal 3 Ratification of Appointment of Independent Registered Public Accountants
The Board recommends a vote “FOR” this proposal.			See page 73

The Audit Committee appointed Deloitte to serve as the Company’s independent registered public accounting firm for fiscal year 2026. The shareholders will be asked to ratify this appointment at the Annual Meeting. A representative of Deloitte is expected to be present at the Annual Meeting and will have the opportunity to make a statement, if desired, and is expected to be available to respond to appropriate questions.

13 2026 Proxy Statement

Proposal 1
Election of Directors

In accordance with our Bylaws, the Board has fixed the number of directors at nine members. The following nominees are standing for re-election to the Board at the meeting: Douglas G. Bergeron, Lisa P. Baird, Ian Harris, Jacob Lamm, Michael K. Passilla, Ellen Richey, Anne M. Smalling, Ravi Venkatesan, and Shannon S. Warren. Directors will be elected to hold office until the 2027 Annual Meeting of Shareholders or until their successors have been duly elected and qualified.

There are no arrangements or understandings between any nominee and any other person pursuant to which he or she was or is to be selected as a director. None of the nominees has a family relationship with any other nominee or director or any executive officer of the Company or any of its subsidiaries. The Board has determined that all the nominees are independent within the meaning of the Nasdaq listing standards other than Mr. Venkatesan, who serves as the Company’s President and Chief Executive Officer (“CEO”). In addition, the Board has determined that Ms. Warren qualifies as an “audit committee financial expert” under SEC rules.

The Board unanimously recommends a vote “FOR” the nine nominees for Director.

2026 Proxy Statement 14

Proposal 1 Election of Directors

Nominees for Election as Director

Information on each of the nominees for the Board, including each nominee’s principal occupation and business experience for at least the last five years, the names of other publicly held companies for which he or she serves as a director or has served as a director in the last five years, and the experience, qualifications, attributes and skills considered among the most important by our Nominating and Corporate Governance Committee and Board in determining that the nominee should serve as a director is set forth below.

Douglas G. Bergeron Chairman of the Board Age: 64 Director since April 2020 Former CEO, VeriFone (2001-2013) Committees: •Compensation •Finance
Mr. Bergeron is the founder and sole shareholder of DGB Investments, Inc., a diversified holding company of technology investments. In 2001, he led the acquisition of VeriFone Systems, Inc. (“Verifone”), a company that provides technology for electronic payment transactions at the point-of-sale, from Hewlett-Packard. In 2002, Mr. Bergeron, as Chief Executive Officer of Verifone, partnered with GTCR and grew VeriFone into a multi-national company with an enterprise value exceeding $4 billion by 2013, when he left the company. Mr. Bergeron is on the Board of Overseers of the Hoover Institution at Stanford University and is a permanent member of the Council on Foreign Relations. Education Mr. Bergeron holds an Honours B.A. in Computer Science from York University in Toronto and a Masters of Science in Systems Management from the University of Southern California in Los Angeles. In 2013, he was awarded an Honorary Doctorate of Laws (LLD) from York University. Qualifications We believe Mr. Bergeron’s extensive experience in the payments industry and his background in finance provide the requisite qualifications, skills, perspectives, and experiences to serve on our Board.

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Proposal 1 Election of Directors

Lisa P. Baird Age: 64 Director since April 2020 President and CEO, NextUp Committees: •Compensation •NCG
Ms. Baird is the President and CEO of NextUp, the leading non-profit member organization providing learning programs and events for Fortune 500 companies. Ms. Baird has extensive experience as a senior executive responsible for sales, communications, marketing, and governance for top sports properties including the NFL, USOPC and NWSL and Fortune 50 companies including IBM, General Motors, Bristol Myers, Johnson & Johnson and the Procter & Gamble Company. Ms. Baird currently serves as an independent director of Alset AI Ventures Inc. (TSXV: GPUS), and has served as an Independent Director on the Board of Fox Racing, which was acquired by Vista Outdoor Inc., Elite Sportswear, L.P., a global leader in sportswear, and Soundview Paper Company, LLC, a consumer paper products company. Current Public Company Directorships •Alset AI Ventures Inc. Education Ms. Baird earned an A.B. in English from Penn State University (1982) where she also earned an MBA from The Smeal College of Business (1984). Qualifications We believe Ms. Baird’s strong communications, marketing, sales and operating experience and a proven record of creating, building, and leading well-known brands provides the requisite qualifications, skills, perspectives, and experiences to serve on our Board.

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Proposal 1 Election of Directors

                Ian Harris Age: 36 Director since February 2022 Chief Financial Officer, Talkspace, Inc. Committee: •Finance •Compensation

Mr. Harris is the Chief Financial Officer of Talkspace, Inc. (NASDAQ: TALK), a leading healthcare technology company that provides virtual behavioral healthcare services. Prior to joining Talkspace, Mr. Harris was a Partner and Managing Director at Hudson Executive Capital, an investment firm that seeks to identify value-oriented opportunities in the small/mid-cap U.S. public markets, from May 2017 to May 2024. Mr. Harris also serves on the board of Liberated Syndication Inc., a leading provider of podcast hosting and advertising services. From August 2020 until February 2022, Mr. Harris also served as an advisor to the Company’s management team and the Board on financial and operational matters. Prior to joining Hudson Executive, Mr. Harris served as an investment banking Associate at Barclays Capital. Education Mr. Harris received his Bachelor of Arts degrees from Brown University. Qualifications We believe Mr. Harris’s familiarity with the Company and his background in corporate finance and investing provides the requisite qualifications, skills, perspectives and experiences to serve on our Board.

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Proposal 1 Election of Directors

      Jacob Lamm Age: 60 Director since April 2020 Founder & Independent Consultant, Enterik Advisory LLC Committees: •NCG •Finance (Chair) Mr. Lamm is founder and Independent Consultant to Enterik Advisory LLC, providing executive and board level consulting services with a focus on organic and inorganic growth strategies. Mr. Lamm was the Chief Operating Officer of InVisionApp Inc., a digital product design platform, from 2020 to 2022. He previously served as Executive Vice President of CA Technologies, a provider of information technology management software and solutions, from 2009 to 2019, where he was responsible for corporate strategy, M&A, venture investing, strategic alliances, and new business incubation. Prior to joining CA Technologies, he co-founded and served as CTO of Professional Help Desk, a provider of Service Management software that was acquired by CA Technologies. Additionally, Mr. Lamm has served as a director of both private and non-profit organizations, serving as a director for the Long Island High Technology Incubator, the New York State Smart Grid Consortium and Watermark Medical Inc., a medical technology company focused on remote diagnostic testing, therapy and patient follow-up, the latter from 2010 to 2018. Education Mr. Lamm earned a B.S. in computer information science from the City University of New York - Brooklyn College in 1987. Qualifications We believe Mr. Lamm’s extensive experience in high-growth technology companies provide the requisite qualifications, skills, perspectives, and experiences to serve on our Board.

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Proposal 1 Election of Directors

Michael K. Passilla Age: 58 Director since April 2020 CEO, Posillipo Ventures, Inc. Committee: •Compensation (Chair)
Mr. Passilla has served as the CEO of Posillipo Ventures, Inc., an investment and advisory services business, since 2018. He previously served as Vice Chairman at Chase Merchant Services, the global payment processing division of JPMorgan Chase & Co, from 2016 to 2018. Prior to that, he was the Chief Executive Officer of Chase Merchant Services from 2013 to 2016. Mr. Passilla was the Chief Executive Officer and President of Elavon, Inc., a global payments processing firm, from 2010 to 2013. Mr. Passilla has been a member of the Board of Directors of Priority Technology Holdings, Inc. (NASDAQ: PRTH), an IT service management company, since 2019, a Strategic Advisor to Optimized Payments, Inc., a consulting and analytics firm specializing in the payments ecosystem, since 2021, a member of the Board of Directors of Bridge2 Solutions, LLC, a SaaS platform technology company, since 2020 (until it was sold to Bakkt), and a member of the Board of Directors of P97 Networks, Inc., a mobile commerce and digital marketing platform, since 2019 up until its sale in April of 2025. Current Public Company Directorships •Priority Technology Holdings, Inc. Education Mr. Passilla earned a BBA from the University of Notre Dame in 1989 and earned an MBA from The J.L. Kellogg Graduate School of Management at Northwestern University in 1995. Qualifications We believe Mr. Passilla’s leadership experience and extensive knowledge of the payments industry provide the requisite qualifications, skills, perspectives, and experiences to serve on our Board.

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Proposal 1 Election of Directors

Ellen Richey Age: 76 Director since April 2020 Former Vice Chair of Risk and Public Policy, Visa Inc. Committees: •Audit and Risk •Finance
Ms. Richey served as Vice Chair of Risk and Public Policy of Visa Inc. (“Visa”), a global payments technology company, from 2014 to 2019, and as Chief Risk Officer from 2017 to 2019. In such roles, Ms. Richey oversaw risk management, including enterprise risk, settlement risk, operational resilience, internal audit, and risks to the integrity of the broader payments ecosystem, and served as a member of Visa’s senior executive committee. During 2014, Ms. Richey concurrently served as Chief Legal Officer, assuming responsibility for the legal function in addition to her risk responsibilities. From 2007 to 2013, Ms. Richey served as Executive Vice President and Chief Enterprise Risk Officer. In that role, she was responsible for oversight of Visa’s compliance, audit and risk teams, including payment system risk, settlement risk and enterprise risk. Ms. Richey serves on the Board of Directors of Green Dot Corporation (NYSE: GDOT), for which she has chaired the Risk and Nominating and Corporate Governance Committees, chairing the Risk Committee since 2023. She also served on the Board of Directors of the Girl Scouts of Northern California, which she chaired, from 2018 to 2022. Current Public Company Directorships •Green Dot Corporation Education Ms. Richey earned a B.A. in Linguistics and Far Eastern Languages from Harvard University (1970) and a J.D. from Stanford University (1977), and served as a law clerk for Associate Justice Lewis F. Powell, Jr., of the United States Supreme Court, from 1979 to 1980. Qualifications We believe Ms. Richey’s extensive experience in the payments industry and in risk management, compliance and audit provide the requisite qualifications, skills, perspectives, and experiences to serve on our Board.

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Proposal 1 Election of Directors

Anne M. Smalling Age: 60 Director since April 2020 President & Managing Partner, HM International, LLC Committees: •Audit and Risk •NCG (Chair)
Ms. Smalling is President and Managing Partner of HM International, LLC (“HMI”), a diversified holding company with a long term investment focus. She provides oversight and supervision of the operating businesses focusing on strategic planning, financing, acquisition and divestitures. Ms. Smalling currently serves as the Chair of the Boards of Directors of Quality Sausage Company, LLC, and American Innovations. She also serves on the Boards of Directors of Igasamex, S. de R.L. de C.V., Garrison Brothers, Organicare and The Savings Group. She formerly served as Chairman of Windsor Quality Food Company, a leader in frozen food manufacturing for consumers and foodservice, from 2004 to 2014. Education Ms. Smalling earned a B.S. in Developmental Psychology from Cornell University (1987) and an MBA from Harvard Business School (1992). Qualifications We believe Ms. Smalling’s operational expertise and experience in strategic planning and financing in a broad range of industries, provide the requisite qualifications, skills, perspectives, and experiences to serve on our Board.

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Proposal 1 Election of Directors

Ravi Venkatesan Age: 49 Director since October 2022 CEO, Cantaloupe, Inc. Committee: •None
Mr. Venkatesan is the Company’s Chief Executive Officer. Mr. Venkatesan served as the Company’s Chief Operating Officer from February 2022 until his promotion as CEO effective October 1, 2022 and prior to that, as the Company’s Chief Technology Officer since December 2020. Prior to joining the Company, Mr. Venkatesan was Head of Innovation at Bakkt Holdings, Inc. (“Bakkt”). He held the dual roles of Chief Technology Officer and Chief Product Officer at Bridge2 Solutions, Inc., preceding its sale to ICE, the parent company of Bakkt. Prior to his position at Bakkt he was the Vice President of Information Technology Strategy and Delivery at Cbeyond, Inc. Earlier in his career he served as a consulting leader with Accenture LLP. Education Mr. Venkatesan graduated from Bangalore University in 1997 with a degree in Electronics and went through a Post Graduate Program in Finance and Information Management from the Management Development Institute in 2000. Qualifications We believe Mr. Venkatesan’s track record of technology leadership and experience in payments companies, as well as his unique understanding of our operations, opportunities and challenges provide the requisite qualifications, skills, perspectives, and experiences to serve on our Board.

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Proposal 1 Election of Directors

    Shannon S. Warren Age: 56 Director since April 2020 Owner & Principal, SSW Consulting LLC Committee •Audit and Risk (Chair)
Ms. Warren is the owner and principal of SSW Consulting LLC, which provides risk and finance advisory services. Ms. Warren was the Chief Control Officer of JPMorgan Chase & Co. (JPM), a global financial services firm, from 2012 to 2016. In this role, she established the Oversight and Control function, designed the framework for the identification and management of operational risk in all products and services offered by JPM, implemented more comprehensive operational risk management technology and managed supervisory regulatory relationships globally. Prior to this role, Ms. Warren was the Corporate Controller and held several additional finance roles at JPM since joining in 2000, and has expertise in accounting and financial reporting matters. Ms. Warren currently serves as a member of the Board of Directors of Firstkey Homes LLC, Member of the Competitiveness Council for Cerberus Operations and Advisory Company, and advisor to Brex, Inc. and Azimuth GRC. Education Ms. Warren is a graduate of the University of Michigan and is a Certified Public Accountant (inactive). Qualifications We believe Ms. Warren’s extensive experience in the payments industry and in compliance and audit provide the requisite qualifications, skills, perspectives, and experiences to serve on our Board.

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Proposal 1 Election of Directors

Nomination Process

Identification and Selection of Nominees

The Nominating and Corporate Governance Committee is responsible for identifying and recommending for selection by the Board nominees for election or re-election to the Board at the annual shareholder meeting, or to fill any vacancies on the Board. The Nominating and Corporate Governance Committee also reviews and makes recommendations to the Board on the range of skills and expertise and other appropriate criteria that should be represented on the Board. The Nominating and Corporate Governance Committee will generally consider all relevant factors in identifying and recommending candidates to the Board, which may include independence, expertise that is useful to the Company and complementary to the background, skills and experience of the other Board members, a commitment to ethics and integrity, a commitment to personal and organizational accountability, a history of achievement that reflects superior standards for themselves and others, and a willingness to express alternate points of view while, at the same time, being respectful of the opinions of others and working collaboratively as a team player. The Nominating and Corporate Governance Committee will consider the following qualifications that it believes would be useful in director candidates:

Payments Industry Experience

Experience in Building a Growth Company

Experience in Bringing Technology to Market

Sales Leadership Experience

Diversity of Background including Gender and Ethnicity

No less than a majority of directors on the Board, as well as all members of the Audit, Compensation, and

Nominating and Corporate Governance Committees, are independent, as required by Nasdaq.

Director Policies and Expectations

Directors are elected each year, there are no term limits for serving on the Board, and there is no mandatory retirement age.

Each member of the Board is expected to ensure that other existing and future commitments, including employment responsibilities and service on the boards of other entities, do not materially interfere with the member’s service as a director. No independent director may serve on the Boards of more than four other public companies, and no employee director may serve on the Boards of more than one other public company.

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Proposal 1 Election of Directors

New Director Candidates

The directors on the Company’s Nominating and Corporate Governance Committee use their available network of contacts when compiling a list of potential director candidates. The Nominating and Corporate Governance Committee also considers potential director candidates recommended by shareholders and other parties, including other directors, and all potential candidates are evaluated based upon the above criteria. The Nominating and Corporate Governance Committee makes no distinction in its evaluation of candidates based upon whether such candidates are recommended by shareholders or other parties.

Shareholders who wish to propose a potential director candidate may submit a recommendation in writing to the Secretary, Cantaloupe, Inc., 101 Lindenwood Drive, Suite 120, Malvern, Pennsylvania 19355, specifying the name of the candidate and stating in detail the qualifications of such person for consideration by the Nominating and Corporate Governance Committee. A written statement from the candidate consenting to be named as a candidate and, if nominated and elected, to serve as a director, should accompany any such recommendation.

Our bylaws also provide for proxy access, which enables eligible shareholders to include their nominees for election as directors in our proxy statement, as well as advance notice provisions, which require shareholders to provide timely notice and specific information when nominating directors or proposing other business to be brought before an annual meeting. For information regarding the eligibility requirements and process to utilize proxy access as well as our advance notice bylaws, see Sections 3.02 and 3.04 of our bylaws and page 84 of this proxy statement.

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Proposal 1 Election of Directors

Director Skills and Experience

The Board annually reviews directors’ skills and expertise to ensure the Board represents a diverse skill set oriented to the historical and emerging needs of the business. The Board has identified the following key qualifications and experience that are important to be represented on the Board as a whole.

Qualification
			Risk Management & Compliance																														5
			Mergers & Acquisitions																														7
			Strategic Planning																														8
			Payments Industry																														6
			Leadership & Senior Management																														9
			Accounting & Finance																														7
			Technology & Cybersecurity																														5

Director Majority Voting Policy

In addition to our Bylaws that provide for a majority vote standard for director elections, the Board has also adopted a Director Majority Voting Policy. Pursuant to the policy, any nominee for director in an uncontested election who receives a greater number of votes “against” his or her election than votes “for” such election shall promptly submit to the Board a letter of resignation to the Secretary of the Company. The Nominating and Corporate Governance Committee will promptly consider the resignation and recommend to the Board whether to accept the tendered resignation or reject it. In considering whether to accept or reject the resignation, the Nominating and Corporate Governance Committee would consider relevant factors such as the underlying reasons for the majority against vote, the length of service and qualifications of the director whose resignation is tendered, the director’s contributions to the Company, and compliance with listing standards. The Nominating and Corporate Governance Committee would then consider the resignation and make a recommendation to the Board. The Board would then act on the Nominating and Corporate Governance Committee’s recommendation, which may include acceptance or rejection of the tendered resignation. The text of the policy is posted on our website at www.cantaloupe.com.

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Corporate Governance

The Company is organized under the laws of the Commonwealth of Pennsylvania and is governed by the Board. The Board is committed to sound business practices, transparency in financial reporting, effective corporate governance and compliance. The Board has adopted a number of governance guidelines and policies which are available on the Corporate Governance page in the “Investors” section of the Company’s corporate website (www.cantaloupe.com). The Board has determined that all of the currently serving members of the Board other than Mr. Venkatesan (our CEO) are independent in accordance with the applicable listing standards of Nasdaq.

Board Leadership Structure

  

Douglas G. Bergeron

Independent, Non-Executive Chair

Ravi Venkatesan

Chief Executive Officer

Independent Committee Chairs
Shannon S. Warren Audit and Risk Committee			Michael K. Passilla Compensation Committee
Anne M. Smalling Nominating and Corporate Governance Committee			Jacob Lamm Finance Committee

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Corporate Governance

The full Board considers periodic rotation of Committee members and chairs, taking into account the desirability of rotation of Committee members and chairs, the benefits of continuity and experience, and applicable legal, regulatory and stock exchange listing requirements.

Our Board currently separates the offices of Chair of our Board and CEO by appointing an independent, non-executive chair. Our Board believes that an independent Board Chair (the “Non-Executive Chair”) is appropriate at this time because it allows our CEO to focus on managing the business and allows the Non-Executive Chair to provide independent leadership for the Board. The arrangement also facilitates our Board’s independent oversight of our executive officers’ management of strategic direction, operational execution, and business risk, thereby better protecting shareholder value. On an annual basis, the Nominating and Corporate Governance Committee recommends, and the majority of the independent directors elect, the Non-Executive Chair. Mr. Bergeron currently serves as our Non-Executive Chair.

The Non-Executive Chair performs the duties and responsibilities set forth in the Charter of the Non-Executive Chair, including the following:

•assist each of the Chairs of the Audit, Compensation, Nominating and Corporate Governance, Finance and Compliance Committees to appropriately execute the functions and responsibilities set forth in each of the Committee’s charters;

•preside at all meetings of the Board, and at executive sessions of the independent Directors;

•coordinate with the CEO to develop an annual schedule for Board meetings, the agenda for each Board meeting, and the distribution of advance meeting materials;

•collaborate with Committee Chairs to facilitate updates to the Board on the activities of their respective Committees;

•encourage and facilitate free and open communication among all Directors;

•coordinate with the CEO to facilitate communications between the executive officers of the Company and the independent Directors, including regular reporting of financial, operational and other performance metrics;

•conduct periodic one-on-one discussions with the independent Directors regarding Board operations and other pertinent issues; and

•ensure timely communication to the CEO of appropriate feedback from executive sessions including recommended actions and issues or concerns raised by independent Directors.

The text of the Charter of the Non-Executive Chair, which was most recently amended on August 6, 2021, is posted on our website at www.cantaloupe.com.

Board Committees
As permitted under Pennsylvania law and the Company’s Articles of Incorporation and Bylaws, the Board has established and delegated certain authority and responsibility to four standing committees: the Audit and Risk Committee, Compensation Committee, Nominating and Corporate Governance Committee and Finance Committee (each, a “Committee”). The Board annually reviews the membership of, and the authority and responsibility delegated to, each committee.

The table below shows the chairs and members of each Committee.

Douglas G. Bergeron

Lisa P. Baird

Ian Harris

Jacob Lamm

Michael K. Passilla

Ellen Richey

Anne M. Smalling

Ravi Venkatesan**

Shannon Warren^

Audit and Risk Committee

Compensation Committee

Nominating and Corporate Governance Committee

Finance Committee

  Member   Chair ** Non-Independent Director ^ Financial Expert

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Corporate Governance

Audit and Risk Committee Members: Shannon S. Warren (Chair) Ellen Richey Anne M. Smalling Number of meetings held in fiscal year 2025: Audit 11 The Audit and Risk Committee engages the Company’s independent accountants, and is primarily responsible for: •appointing, retaining and replacing the Company’s independent auditor •approving the services performed by, and compensation paid to, the Company’s independent auditor •pre-approving any non-audit services (and related fees) to be performed by the Company’s independent auditor •pre-approving any prospective transactions with officers, directors, holders of more than 5% of our securities, and any member of the immediate family of or entity affiliated with any of the forgoing persons •reviewing and discussing the Company’s accounting principles •oversee the Company’s internal audit function •evaluate the independence of independent auditors •reviewing and discussing with management and the Company’s independent auditor the Company’s quarterly financial statements prior to the filing of the Company’s quarterly reports on Form 10-Q filings •discussing with management the Company’s earnings press releases •discussing with management and the independent auditor any major issues as to the adequacy of the Company’s internal controls •recommending to the Board whether the audited financial statements should be included in the Company’s Annual Report •produce the Audit and Risk Committee report for inclusion in the Company’s proxy statement and annual report •overseeing the Company’s compliance functions •supervising the Company’s Chief Legal and Compliance Officer, who leads the Company’s compliance program. Also regularly receives updates from the Company’s Chief Legal and Compliance Officer on business risks, compliance and ethics issues. •periodically reviewing and recommending to the Board any changes to the Company’s Code of Business Conduct and Ethics •reviewing and monitoring significant compliance risk areas and the steps management takes to monitor, control and report such compliance risk exposures, including compliance risks related to information security and cybersecurity The Audit and Risk Committee operates pursuant to a charter that was most recently amended on November 4, 2024, a copy of which is accessible on the Company’s website, www.cantaloupe.com.

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Corporate Governance

Compensation Committee Members: Michael K. Passilla (Chair) Lisa P. Baird Douglas G. Bergeron
Ian Harris Number of meetings held in fiscal year 2025: 5 The Compensation Committee is responsible for: •reviewing and recommending compensation and compensation plans, policies and programs for the directors and executive officers of the Company •administering the Company’s incentive compensation and equity-based plans •annually reviewing and recommending for approval by the Board corporate goals and objectives relevant to the Chief Executive Officer and other executive officers’ compensation •evaluating the Chief Executive Officer and other executive officers’ performance in light of those goals and objectives •recommending for approval to the Board the Chief Executive Officer’s and other executive officers’ compensation levels based upon this evaluation •having the authority to retain or obtain the advice of a compensation consultant or other advisor, and to be directly responsible for the appointment, compensation and oversight of the work of any such advisor •produce the Compensation Committee Report for inclusion in the Company’s proxy statement and annual report The Compensation Committee operates pursuant to a charter that was most recently amended on October 21, 2024, a copy of which is accessible on the Company’s website, www.cantaloupe.com.

Compensation Committee Interlocks and Insider Participation

No member of the Compensation Committee was, during fiscal 2025, an officer or employee of the Company or any of our subsidiaries, or was formerly an officer of the Company or any of our subsidiaries, or, except as described herein, had any relationships requiring disclosure by us under Item 404 of Regulation S-K of the General Rules and Regulations of the Securities and Exchange Commission (“Item 404”).

During fiscal 2025, none of our executive officers served as: (i) a member of the compensation committee (or other committee of the Board of Directors performing equivalent functions or, in the absence of any such committee, the entire Board of Directors) of another entity, one of whose executive officers served on our Compensation Committee; (ii) a director of another entity, one of whose executive officers served on our Compensation Committee; or (iii) a member of the compensation committee (or other committee of the Board of Directors performing equivalent functions or, in the absence of any such committee, the entire Board of Directors) of another entity, one of whose executive officers served as a director on our Board of Directors.

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Corporate Governance

Nominating and Corporate Governance Committee Members: Anne M. Smalling (Chair) Lisa P. Baird Jacob Lamm Number of meetings held in fiscal year 2025: 4 The Nominating and Corporate Governance Committee is responsible for: •reviewing corporate governance policies and systems against applicable laws, regulations, and industry specific standards and practices, if any, including any securities regulatory authority or Nasdaq guidelines applicable to the Company and recommending any changes to the Board. Such review includes reviewing and recommending to the Board for approval any changes to the documents, policies and procedures in the Company’s governing documents, including its articles of incorporation and bylaws •identifying best practices and developing and recommending to the Board corporate governance principles •overseeing, periodically reviewing and reporting to the Board on the Company’s policies, practices, goals and programs relating to environmental, sustainability, corporate social responsibility, health, safety, and corporate governance matters (collectively, “ESG”) •in consultation with management, annually reviewing the directors’ and officers’ liability policy, including its coverage and terms •providing to the Board the Nominating and Corporate Governance Committee’s assessment of which directors should be deemed independent directors under applicable rules and regulations of the SEC and Nasdaq •establishing procedures for, conducting and administering an annual performance and effectiveness evaluation of the Board and reporting annually to the Board the results of its assessment •on an annual basis, recommend the director to serve as the Non-Executive Chair to the full board for approval •in consultation with the Chair, making recommendations to the Board regarding the composition of the Board Committees, annually reviewing the composition of each Committee and presenting recommendations for Committee memberships to the Board, as needed The Nominating and Corporate Committee operates pursuant to a charter that was most recently amended on October 31, 2024, a copy of which is accessible on the Company’s website, www.cantaloupe.com.

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Corporate Governance

Finance Committee Members: Jacob Lamm (Chair) Douglas G. Bergeron Ian Harris Ellen Richey Number of meetings held in fiscal year 2025: 4 The Finance Committee is responsible for: •monitoring the Company’s capital structure, financial condition and requirements for funds and recommend from time to time an overall financial strategy to the Board •assisting the Board in reviewing and monitoring the Company’s capital structure and financial plans, including short-term and long-term debt programs and equity financings •reviewing target financials and valuations in connection with potential acquisitions •taking or authorizing necessary actions to effect financings, refinancings and refundings within the limits set by the Board The Finance Committee operates pursuant to a charter that was most recently amended on October 28, 2024, a copy of which is accessible on the Company’s website, www.cantaloupe.com.

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Corporate Governance

Board Operations

Meetings of the Board of Directors

The Board of the Company and the Board Committees collectively held a total of thirty-one (31 meetings during the fiscal year ended June 30, 2025. Each member of the Board attended at least 75% of the aggregate number of meetings of the Board and Board Committees of which he or she was a member. The Company’s policy regarding directors’ attendance at the annual meeting of shareholders, as described in the Company’s Corporate Governance Guidelines, is that all directors are strongly encouraged to attend the Annual Meeting. All of our directors attended the 2025 Annual Meeting.

Director Orientation and Continuing Education

The Nominating and Corporate Governance Committee works with management to provide an orientation for new directors. The Board encourages directors to participate in continuing education, as well as participation in accredited director education programs. Continuing education for all directors is conducted throughout the year through a variety of presentations and programs. During fiscal 2025, our ongoing director education included Nasdaq training sessions covering a variety of topics, including:

•ESG-related issues sustainability, human capital management

•enterprise risk management and geopolitical risks

•regulatory compliance and corporate governance

Executive Sessions

The independent members of the Board meet regularly in executive sessions. The independent Board members may meet in executive session at regular Board meetings or at other times, in each case, if deemed necessary, but no less than twice a year.

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Corporate Governance

Additional Board Engagement

Management is encouraged to invite Company personnel to any Board meeting at which their presence and expertise would help the Board have a full understanding of matters being considered. Our directors also regularly engage in one-on-one meetings with management and other company personnel. Members of our Board are also active in our investor relations efforts, including one-on-one engagement with current and potential investors and participating in various industry conferences, functions and initiatives, including the 2025 NAMA show. We believe these efforts enable the Board and management to understand, consider and address the issues that matter most to our shareholders.

Annual Performance Evaluation of the Board

The Nominating and Corporate Governance Committee establishes procedures for, and conducts and administers, an annual performance and effectiveness evaluation of the Board. Each Committee also conducts an annual review of its own performance. The Nominating and Corporate Governance Committee then reviews and provides feedback on the annual self-assessment process including specific topics to be addressed. The fiscal 2025 evaluation process produced constructive feedback aimed at improving the performance and contribution of the Board and each Committee, with appropriate action plans developed to address the feedback.

Board’s Role and Oversight Responsibilities

Strategy and Performance It is the duty of the Board to oversee management’s performance to ensure that the Company operates in an effective, efficient and ethical manner in order to produce value for the Company’s shareholders. Risk Management The Board has ultimate responsibility for overseeing management’s approach to risk management. Succession Planning The Board selects the Company’s Chief Executive Officer in the manner that it determines to be in the best interests of the Company’s shareholders.

   Cybersecurity    Sustainability    Human Capital Management

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Corporate Governance

Oversight of Strategy, Risk and Performance

The Board is responsible for the overall oversight of management in the execution of its responsibilities. In this oversight role, and in conjunction with the Audit and Risk Committee, the Board regularly reviews the Company’s long-term business strategy and works with management to set the short-term and long-term strategic objectives of the Company and to monitor progress on those objectives. The Board as a whole is responsible for risk oversight at the company, with reviews of certain areas being conducted by the relevant board committees that regularly report to the full Board, in particular, the Audit and Risk Committee. In its risk oversight role, the Board reviews, evaluates and discusses with appropriate members of management whether the risk management processes designed and implemented by management are adequate in identifying, assessing, managing and mitigating material risks facing the Company, including financial, international, operational, social and environmental risks.

Committee Oversight of Risk

The Board of Directors is responsible for overseeing management’s approach to risk management

Various Committees of the Board assist the Board in fulfilling that responsibility:

Audit and Risk Committee •assists the Board in its oversight of risk management in the areas of financial reporting, internal audit function, and compliance with legal and regulatory requirements related to financial reporting and auditing matters •reviews and monitors significant compliance risk areas and the steps management takes to monitor, control, and report such compliance risk exposures, including technology and cybersecurity

Compensation Committee •oversees our risk management activities with respect to our compensation policies and practices

Nominating and Corporate Governance Committee •oversees risks associated with our overall corporate governance framework, principles, policies and practices

Finance Committee •assists the Board in reviewing and monitoring risks associated with the current and long-range financial policies and strategies of the Company

Management is responsible for managing the risks that the Company faces, identifies material risks facing the Company on an ongoing basis and discusses those risks with the Board or its Committees, as appropriate

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Corporate Governance

Enterprise Risk Management

The Company has established an Internal Audit function responsible for evaluating the adequacy of the Company’s internal control framework and management’s assessment of the effectiveness of internal controls, assessing compliance with the Company’s policies and procedures, reviewing operations to ascertain whether results are consistent with established objectives and operating effectively, and assessing and reporting on the Company’s operational and financial risk, among other things. The Internal Audit function reports directly into the Audit and Risk Committee and provides the Audit and Risk Committee with an independent view of the Company’s internal controls framework and management’s assessment of the effectiveness of internal controls over financial reporting.

Cybersecurity

•Cybersecurity risk management is a vigilant, proactive priority across our organization.

•Protecting the Company’s systems and our data from cyberattacks and unintentional or malicious breaches is a priority for the Company’s Board and management.

•The Board and management actively oversee the management of cybersecurity risks through our enterprise risk management programs.

•The Board also reviews and monitors compliance risks related to information security and cybersecurity, including the steps management takes to monitor, control and report such compliance risk exposures.

Sustainability

•Sustainability issues and initiatives are a priority for the Board and management.

•Our Board has overall accountability for the Company’s sustainability performance, risk management and strategic direction, and may delegate responsibility for reviewing sustainability initiatives and performance.

•Board committees and management report to the Board on sustainability matters, strategy and risk management.

•The Nominating and Corporate Governance Committee oversees and is responsible for reviewing and reporting to the Board on the Company’s sustainability policies, practices, goals and programs.

Human Capital Management (HCM)

•We believe our ability to attract, develop and retain the most qualified candidates in all areas of our business is critical to our future success and growth.

•We prioritize and continue to invest in helping our employees grow professionally in their career. We offer a combination of interactive professional development trainings, access to on demand online courses through our learning management system, and group learning programs.

• We use an annual employee engagement survey to inform the ongoing development of our employee programs and resources. The survey reflects questions to gauge employee sentiments toward current trends and issues including company direction and strategy, communication by management, individual development, team culture, and overall satisfaction. With the information provided by the annual engagement survey, leadership is provided key insights and valuable feedback which we continue to implement in our Company-wide action plans with the intent to focus on key areas to prioritize, enhance, and drive continued increase in employee engagement, learning and development, and professional growth for our employees.

36 2026 Proxy Statement

Corporate Governance

CEO and Management Succession Planning

The Chairman of the Board conducts the Chief Executive Officer’s annual performance review leveraging input from all Directors of the Board.

The Chief Executive Officer prepares, and the Board reviews, on an annual basis, an emergency short-term succession contingency plan should an unforeseen event, such as death or disability, occur that prevents the Chief Executive Officer from continuing to serve.

Other Governance Policies and Practices

Governance Guidelines

The Corporate Governance Guidelines are reviewed periodically by the Nominating and Corporate Governance Committee, and the Board makes changes when appropriate based on recommendations from the Committee. The Corporate Governance Guidelines were most recently amended on August 12, 2022. A copy of the Corporate Governance Guidelines is posted on our website at www.cantaloupe.com. The Board annually reviews the Company’s corporate governance policies and practices in light of the requirements of applicable law and the listing standards of Nasdaq.

Among other things, our Corporate Governance Guidelines provide that (i) directors who are not independent may not serve on the boards of more than one other public company in addition to the Board and (ii) independent directors may not serve on the Boards of more than four other public companies in addition to the Board.

Code of Business Conduct and Ethics

We have adopted a Code of Business Conduct and Ethics (the “Code of Conduct”) that applies to all of our directors, officers and employees. The Code of Conduct is posted on our website at www.cantaloupe.com. The Board must grant any waiver from a provision of the Code of Conduct to any executive officer or director, and any such waiver will be disclosed as required by law or stock market regulation.

Certain Relationships and Related Party Transactions

We have adopted a formal written policy, which is set forth in our Audit and Risk Committee Charter, that our Audit and Risk Committee review and approve all related-party transactions, defined by, or those transactions required to be disclosed under, Item 404 of Regulation S-K. Executive officers, directors, holders of more than 5% of any class of our voting securities, and any member of the immediate family of, and any entity affiliated with, any of the foregoing persons, are not permitted to enter into a related person transaction with us without the prior consent of our Audit and Risk Committee. Any request for us to enter into a transaction with an executive officer, director, principal shareholder, or any of their immediate family members or affiliates, in which the amount involved exceeds $120,000 is considered a “related party transaction” and must first be presented to our Audit and Risk Committee for review, consideration and approval. In approving or rejecting any such proposal, our Audit and Risk Committee is to consider the relevant facts and circumstances available and deemed relevant to the Audit and Risk Committee, including, but not limited to, whether the transaction is on terms no less favorable than terms generally available to an unaffiliated third party under the same or similar circumstances and the extent of the related person’s interest in the transaction.

In addition, under our Code of Business Conduct and Ethics, our executive officers and directors have a responsibility to disclose any transaction or relationship that reasonably could be expected to interfere with their exercise of

2026 Proxy Statement 37

Corporate Governance

independent judgment or materially impair the performance of their responsibilities to our Board, which shall be responsible for reviewing such transaction or relationship and determining whether any action needs to be taken.

Other Transactions with Related Persons

In determining director independence, our Board reviews other transactions with related persons. As required by Item 407(a)(3) of Regulation S-K, our Board considered the following transaction in evaluating Mr. Passilla’s independence:

Mr. Passilla serves as a strategic advisor to Optimized Payments, Inc. (“Optimized”), a consulting firm that we utilize for payments analytics and advisory services. The Company uses these services in analysis, comparison and negotiation of our interchange and other processing fees charged by payment processors and credit card networks. As consideration for the services, we pay the consulting firm a subscription fee, as well as success fee for certain savings realized by the Company. Mr. Passilla does not have a material interest in the Company’s arrangement with Optimized. Mr. Passilla’s aggregate ownership interest in Optimized is less than 10% and, in accordance with Item 404, the Board determined that Mr. Passilla did not have a direct or indirect material interest in the transaction. The company paid $0.2 million and $0.2 million to Optimized for the years ended June 30, 2025 and 2024, respectively.

In addition, the Board considered Mr. Harris’ role as an advisor to the Company from August 2020 until February 2022, and has determined that such prior affiliations and relationships would not interfere with his ability to exercise independent judgment in carrying out his responsibilities as a director of the Company.

Shareholder Communications with the Board of Directors

Our Board has established a formal process for shareholders to send communications to the Board or individual directors. Shareholders may send communications to the Board or individual directors by e-mail at corporatesecretary@cantaloupe.com, or by mail at 101 Lindenwood Drive, Suite 120, Malvern, Pennsylvania 19355, Attn: Corporate Secretary.

All communications submitted under this policy will be received and processed by the Secretary of the Company and submitted to the Board or the requisite individual members of the Board, as appropriate, based on the facts and circumstances outlined in the communication. Communications may also be referred to other departments within the Company or to management rather than to the Board or any of its members. The Board has requested that certain items which are unrelated to the duties and responsibilities of the Board should generally not be furnished to the Board, such as product complaints, product inquiries, new product suggestions, resumes and other forms of job inquiries, surveys, business solicitations or advertisements, or communications which are primarily commercial in nature. In addition, material that is unduly hostile, threatening, illegal or similarly unsuitable will be excluded from distribution to the Board or any of its members. The Secretary will make available to any non-employee member of the Board any communication that is not distributed to the Board in accordance with the process described above at the director’s request.

38 2026 Proxy Statement

Compensation of Non-Employee Directors
Director Compensation Program

The Compensation Committee annually reviews and recommends for approval to the Board the compensation of the directors. Members of the Board who are not employees of the Company receive cash and equity compensation for serving on the Board, as reviewed and recommended by the Compensation Committee, with subsequent approval thereof by the Board.

Director Compensation Mix			Additional annual cash retainers:
			Chair of the Board			$35,000
			Audit and Risk Committee Chair			$25,000
			Compensation Committee Chair			$10,000
			Nominating and Governance Committee Chair			$7,500
			Finance Committee Chair			$10,000

*    vesting on the first anniversary of the grant date (but eligible for prorated vesting upon separation of service for each completed calendar quarter of service following the grant date).

No additional cash retainers are provided for non-Chair service on Board committees, we do not pay our directors meeting attendance fees under the program, and cash retainers are generally payable monthly in arrears.

In addition to these cash retainers, and reflective of the Compensation Committee’s and the Board’s belief that equity compensation is key in linking the interests of our non-employee directors and our executives with those of our shareholders, our non-employee directors are eligible to receive an annual grant of restricted stock units (“RSUs”) worth approximately $150,000, vesting on the first anniversary of the grant date (but eligible for prorated vesting upon separation of service for each completed calendar quarter of service following the grant date). In accordance with this program, each of our non-employee directors serving on the Board as of May 12, 2025 received a grant of 19,157 RSUs.

39 2026 Proxy Statement

Compensation of Non-Employee Directors

Stock Ownership Guidelines

The Board has adopted the Stock Ownership Guidelines (the “Guidelines”) for directors and executive officers. Under the Guidelines, the Chief Executive Officer is required to own shares of Common Stock with a value of at least three times his or her base salary, and the Chief Financial Officer and other executive officers are required to own shares of Common Stock with a value of at least one times his or her base salary. The executive officers have five years to attain such level of ownership. Each non-employee director is required to own shares of Common Stock with a value of at least five times the sum of his or her annual cash retainer. Each non-employee director has five years to comply following the commencement of his or her service on the Board. As of the date of this proxy statement, each executive officer and director is in compliance with the applicable stock ownership requirements or is in the applicable grace period for compliance. The Guidelines are posted on our website at www.cantaloupe.com.

Fiscal Year 2025 Director Compensation

The table below summarizes the compensation of each individual who served as a non-employee director during the fiscal year ended June 30, 2025. In addition, the footnotes below include the outstanding equity awards held by each non-employee director as of June 30, 2025.

Name			Fees Earned or Paid in Cash ($)						Stock Awards ($)(1)						Total ($)
Douglas G. Bergeron, Chair(2)						$    85,000						$	100,000.00					$	185,000.00
Lisa P. Baird(2)						$    50,000						$	100,000.00					$	150,000.00
Ian Harris(2)						$    50,000						$	100,000.00					$	150,000.00
Jacob Lamm(2)						$    57,500						$	100,000.00					$	157,500.00
Michael K. Passilla(2)						$    60,000						$	100,000.00					$	160,000.00
Ellen Richey(2)						$    60,000						$	100,000.00					$	160,000.00
Anne M. Smalling(2)						$    57,500						$	100,000.00					$	157,500.00
Shannon S. Warren(2)						$    75,000						$	100,000.00					$	175,000.00

(1)The grant date fair value of the RSU awards shown in this column are computed in accordance with FASB ASC Topic 718. Please see Note 12 - ("Stock Based Compensation Plans") to the Company's consolidated financial statements for the fiscal year ending June 30, 2025, as filled on Form 10-K with the SC on September 8, 2025, for further information on how we compute the value of equity awards.

(2)As of June 30, 2025, (i) directors Bergeron, Baird, Lamm, Passilla, Richey, Smalling, and Warren each had 120,000 unexercised stock options outstanding (which were granted on May 6, 2020 and have an exercise price of $6.49 per share) and (ii) director Harris had 87,500 unexercised stock options outstanding (which were granted on February 7, 2022 and have an exercise price of $8.02), in each case, with 25% of such options vesting on the first anniversary of the grant date (but eligible for prorated vesting upon separation of service for each completed calendar quarter of service following the grant date), and the remaining 75% of such options vesting in equal quarterly installments over the three-year period following the first anniversary of the grant date. Each of these directors also have 19,157 RSUs that will vest on May 12, 2025.

40 2026 Proxy Statement

Certain Information About Management

Executive Officers

Name			Age			Position(s)
Ravi Venkatesan			49			Chief Executive Officer
Scott Stewart			52			Chief Financial Officer
Jeffrey Dumbrell			56			Chief Revenue Officer
Anna Novoseletsky			48			Chief Legal and Compliance Officer and General Counsel
Jared Grachek			39			Chief Accounting Officer

The following is detailed information about each of our executive officers other than Mr. Venkatesan whose biographical information is included under “Proposal 1: Election of Directors” above.

Scott Stewart Chief Financial Officer since February 2022 Age: 52 As Chief Financial Officer, Mr. Stewart oversees the Company’s finance organization, including financial strategy and operations, accounting and financial reporting, planning and analysis, tax, treasury, and investor relations. Prior to becoming Chief Financial Officer, Mr. Stewart served as the Chief Accounting Officer of Cantaloupe from September 2020 until January 2022. Mr. Stewart joined Cantaloupe after serving 13 years with the Intercontinental Exchange (ICE), which operates exchanges and clearing houses across the globe, such as the New York Stock Exchange (NYSE), and provides data services and technology solutions to financial institutions, investors and corporations. During his time at ICE, Mr. Stewart served in various positions, most recently as Assistant Controller, where his responsibilities included managing and overseeing the production of external financial statements, implementation of new accounting standards, maintaining corporate controls and ensuring SOX compliance across all accounting processes. Following ICE’s acquisition of NYSE, Mr. Stewart supervised the integration of NYSE’s accounting function into ICE’s accounting group, including the transition of employees, consolidation of job functions, roles and responsibilities, and moving the NYSE accounting function from New York to Atlanta. Prior to his employment with ICE, Mr. Stewart was a Senior Auditor at Ernst & Young from 2003 until 2007. A graduate of Clemson University, Mr. Stewart holds both a Bachelor of Science in Accounting and Master of Professional Accountancy. He is also a certified public accountant.

41 2026 Proxy Statement

Jeffrey Dumbrell Chief Revenue Officer since January 2022 Age: 56 Mr. Dumbrell has over 20 years of experience building and scaling high-performing payments and technology organizations globally. Prior to joining Cantaloupe, Mr. Dumbrell served as Senior Vice President, Strategic Partnerships at Boost Payment Solutions from July 2021 until December 2021. From 2018 to 2021, Mr. Dumbrell was a partner at Boyden Global and president at SCP Holdings, Inc. From 2013 until 2016, Mr. Dumbrell co-founded and was CEO of PowaPOS, a B2B infrastructure provider of tablet and smartphone-based payments technology for the point-of-sale industry, prior to its sale to SuperCom (Nasdaq: SPCB) in 2016. From 2008 to 2013, Dumbrell served as EVP of Europe, Middle East, Africa and Asia Pacific at VeriFone Systems, Inc. where revenue grew during his tenure from approximately $350 million to over $900 million across 50+ countries. Prior to that role, Dumbrell led VeriFone’s North America effort for five years, growing revenue to over $350 million. While at VeriFone he expanded the company’s highly successful channel partnership relationships in the US, Canada, and throughout Europe and the Middle East.

Anna Novoseletsky Chief Legal and Compliance Officer & General Counsel, Corporate Secretary since January 2023 Age: 48 Ms. Novoseletsky is a seasoned attorney with expertise in global payments, digitization, and e-commerce. Prior to joining Cantaloupe, Ms. Novoseletsky was VP & Associate General Counsel and Head of Legal at Discover Financial Services, where she partnered with senior executives to set strategy within the payments business to evaluate risk on various global business initiatives, focused on corporate governance and regulatory framework of the payments service industry, and was General Counsel for Discover Network, PULSE Network, and Diners Club International. Ms. Novoseletsky earned her Juris Doctor degree from Northwestern University School of Law and her Bachelor and Master of Laws from the Ukrainian State Law Academy with highest honors. Ms. Novoseletsky is an active member of the Legal Aid Society’s Advisory Board of the Metropolitan Family Services of Chicago and devotes significant time to volunteerism and pro bono work. Previously she practiced at Latham & Watkins LLP, one of the premier global business law firms, where she started her practice focusing on public and private mergers and acquisitions and advising independent directors in conflict-of-interest transactions, and public company representation. Prior to that role, Ms. Novoseletsky started her legal career in Russia and Ukraine, practicing law under the umbrella of a consulting company in Moscow.

42 2026 Proxy Statement

Certain Information About Management

Jared Grachek Chief Accounting Officer since May 2023 Age: 39 As Chief Accounting Officer, Mr. Grachek serves as Cantaloupe’s principal accounting officer, overseeing all accounting and financial reporting processes. From April 2021 to May 2023, Mr. Grachek worked as the Controller for Lending Point, a large private equity backed financial technology company, where he was directly responsible for all accounting operations including financial reporting, technical accounting, and tax compliance. From May 2008 to March 2021, Mr. Grachek worked in the audit practice at the accounting firm Ernst & Young where he served public and private companies in the financial technology and capital markets industries. Mr. Grachek is a financial professional with more than fifteen years of combined industry and public accounting (Big 4) experience supporting SEC registrants and rapidly growing private companies externally though audit and consulting engagements and internally through the controllership function. Mr. Grachek earned his Master's in Business Administration from Emory University Goizueta Business School, his Master of Science in Accountancy from the University of Notre Dame - Mendoza College of Business and his Bachelor of Business Administration in Finance from the University of Georgia -Terry College of Business. Mr. Grachek is also a Certified Public Accountant.

There are no family relationships among our directors or executive officers.

2026 Proxy Statement 43

Proposal 2
Advisory Vote to Approve Compensation of Named Executive Officers

As required by Section 14A of the Exchange Act, shareholders are entitled to a non-binding vote on the compensation of our named executive officers (sometimes referred to as “say-on-pay”). At the 2025 Annual Meeting of Shareholders held on November 20, 2024, our shareholders expressed support for the Company’s fiscal 2024 NEO compensation programs, with our advisory “say-on-pay” vote receiving over 98% support.

We are asking our shareholders to indicate their support and approval for our named executive officer compensation, as described under the Compensation Discussion and Analysis section of this proxy statement, including the tables that follow which describes in detail our executive compensation programs and the decisions made by the Compensation Committee and our Board. In deciding how to vote on this proposal, the Board encourages you to read the Compensation Discussion and Analysis and the tables that follow.

The Board recommends that shareholders approve, on an advisory basis, the following resolution:

“RESOLVED, that the compensation paid to the Company’s named executive officers, as disclosed pursuant to Item 402 of Regulation S-K, including the Compensation Discussion and Analysis, compensation tables and narrative discussion, in the Company’s proxy statement for the 2026 Annual Meeting of Shareholders, is hereby approved. The say-on-pay vote is advisory, and therefore not binding on the Company, the Compensation Committee or our Board of Directors. However, our Board of Directors and our Compensation Committee value the opinions of our shareholders, and, to the extent there is any significant vote against the named executive officer compensation as disclosed in this proxy statement, they will consider any shareholder’s concerns, and the Compensation Committee will evaluate whether any actions are necessary to address those concerns.”

The affirmative vote of a majority of the votes cast by all holders of the issued and outstanding shares of Common Stock and Series A Preferred Stock voting together (with each share of Common Stock entitled to one vote, and each share of Series A Preferred Stock entitled to 0.1988 of a vote, with any fractional vote being rounded to the nearest whole number) is required for approval of this proposal.

The Board of Directors recommends that you vote, on an advisory basis, “FOR” the proposal to approve the compensation of the named executive officers.

2026 Proxy Statement 44

Compensation Discussion & Analysis

The following Compensation Discussion and Analysis (“CD&A”) provides information regarding our executive compensation philosophy, the elements of our executive compensation program, and the factors that were considered in the compensation actions and decisions for our named executive officers during fiscal 2025. The CD&A should be read together with the compensation tables and related disclosures set forth elsewhere in this proxy statement.

Our Compensation Committee has been actively restructuring our compensation programs since fiscal 2022 and through fiscal 2025 to accommodate changes in our management team and to design and implement a program that the Compensation Committee believes aligns with the Company’s long-term strategic plan, reflects our pay-for-performance philosophy, encourages retention of key executives, and increases alignment between the interests of our executives and our shareholders.

Our Named Executive Officers

During fiscal 2025, our named executive officers (“NEOs”) were as follows:

Ravi Venkatesan Chief Executive Officer

Scott Stewart Chief Financial Officer

Jeffrey Dumbrell Chief Revenue Officer

Gaurav Singal Former Chief Technology Officer(1)

Anna Novoseletsky Chief Legal and Compliance Officer

(1)Mr. Singal resigned from the Company, effective as of October 7, 2025.

45 2026 Proxy Statement

Compensation Discussion & Analysis

Table of Contents

Compensation Discussion & Analysis			45
CD&A At-A-Glance			47
Our Compensation Philosophy			47
Compensation Process			50
Fiscal Year 2025 Executive Compensation			51
Executive Officer Employment Arrangements			58
Compensation Policies and Practices			60
Compensation Committee Report			61

Executive Compensation Tables and Related Disclosures			62
Summary Compensation Table			62
Grants of Plan-Based Awards			63
Outstanding Equity Awards at Fiscal Year-End			64
Option Exercises and Stock Vested			65
Potential Payments Upon Termination or Change of Control			65
CEO Pay Ratio Disclosure			67
Pay Versus Performance			68
Policies and Practices for Granting Certain Equity Awards			72

46 2026 Proxy Statement

Compensation Discussion & Analysis

CD&A At-A-Glance

Fiscal Year 2025 Compensation Highlights

Elements of Compensation

The components of our NEO compensation program are summarized in the below table, and more detailed discussions of each component follow:

Element

Key Characteristics

Why We Pay this Element

How We Determine

Base Salary

•Fixed compensation component payable in cash. Reviewed annually and adjusted when appropriate.

•Provide a base level of competitive cash compensation for executive talent.

•Experience, job scope, and individual performance. •Market and peer data.

Annual Bonus

•Variable compensation component payable in cash based on performance as compared to Company and/or individual performance goals.

•Motivate and reward executives for performance on key operational, financial, and personal measures during the year.

•Organizational and/or individual performance. Discretionary bonuses are based on various factors, including past performance. •Market and peer data. •2025 Financial Goals Based on: Revenue, Adjusted EBITDA, Monthly Recurring Revenue Growth.

Equity Awards

•Variable compensation component payable in restricted stock, restricted stock units, and/or stock options.

•Alignment of long-term interests of management and shareholders and retention of executive talent.

•Organizational and/or individual performance. •Outstanding Performance-Based Options Goals Based on: Share Price.

Perquisites and Other Personal Benefits

•Provide basic competitive health, welfare, and 401(k) benefits.

•Provide market-standard benefits programs to our workforce.

•Periodic review of benefits provided generally to all employees.

2026 Proxy Statement 47

Compensation Discussion & Analysis

Incentive Plan Performance

Annual bonuses for fiscal year 2025 were awarded based on the achievement of predetermined corporate goals and the Board of Directors discretionary evaluation (discretion made up 15% of the predetermined corporate goals). The corporate goals were based on the Company’s Adjusted EBITDA (40%), Revenue (25%), Monthly Recurring Revenue Growth (20%), as detailed in the table below:

Annual Bonus

Revenue ($)			Adjusted EBITDA ($)(1)			Monthly Recurring Revenue Growth (%)(2)

Performance-Based Options

(1)We define Adjusted EBITDA as U.S. GAAP net income before (i) interest income, (ii) interest expense, (iii) income tax provision, (iv) depreciation, (v) amortization, (vi) stock-based compensation expense, and (vii) certain other significant infrequent or unusual losses and gains that are not indicative of our core operations such as (a) investigation, proxy solicitation and restatement expenses, net of insurance recoveries, (b) integration, acquisition, due diligence, and license application expenses, (c) costs as a result of auditor transitions, (d) severance, and (e) remediation expenses.

(2)We define Monthly Recurring Revenue Growth as the increase in revenue generated from subscription services during the fiscal year and use this metric as we believe it appropriately incentivizes our NEOs to achieve sustainable growth, which setting challenging goals that, if achieved, will deliver value to our shareholders.

Fiscal Year 2025 Say on Pay Results

At the 2025 Annual Meeting of Shareholders held on November 20, 2024, over 98% of our shareholders expressed support for the Company’s fiscal 2024 NEO compensation programs through our advisory “say-on-pay” vote. We believe that this strong show of support reflects the evolution of our compensation programs to fit our new go-forward strategy, and our Compensation Committee’s increased emphasis of equity-based compensation to further link our executive compensation programs with shareholder interests and provide attractive equity growth opportunities to continue to attract and retain key talent, all in line with our pay-for-performance philosophy.

As our executive compensation programs continue to evolve, our Compensation Committee values shareholder feedback, and will consider any shareholder suggestions and commentary related to our compensation practices and structures, whether through our annual “say-on-pay” votes or otherwise.

48 2026 Proxy Statement

Compensation Discussion & Analysis

Our Compensation Philosophy

The Company’s compensation philosophy is designed to attract and retain key executives responsible for our success, reflect pay-for-performance, and align management’s interests with the creation of long-term shareholder value. The Compensation Committee believes that these goals are best accomplished by tying a significant portion of compensation to the achievement of performance goals and equity incentives.

Emphasis on Equity Awards

In particular, the Compensation Committee believes that equity awards are an essential component of an effective compensation program because they provide a direct link between our shareholders’ interests and our employees, executive officers, directors, and advisors. The Compensation Committee - and the Board - believe that this link is key to the future success of the Company and have been working to implement changes in the Company’s compensation programs to emphasize equity compensation. A more prominent role for equity compensation in our programs also enhances equity ownership in the Company by our employees, executive officers, and directors, which our Compensation Committee and Board believe is essential to increasing shareholder alignment. The Compensation Committee firmly believes that the Company can best attract and retain key talent by providing attractive “upside” growth opportunity if our leadership succeeds in improving our Company’s past performance, which is directly aligned with our shareholder interests. For further information on our equity award program for our NEOs, please see the below discussion under “-Equity Awards.”

Other elements of our compensation program include base salary, annual bonuses, and limited perquisites. For more information, please see the below discussion under “Fiscal Year 2025 Executive Compensation.”

2026 Proxy Statement 49

Compensation Discussion & Analysis

Compensation Process

Roles and Responsibilities

Compensation Committee

Chief Executive Officer

Compensation Consultant

The Compensation Committee is responsible for annually reviewing and recommending to the Board for approval the corporate goals and objectives relevant to the compensation of the executive officers of the Company, evaluating the executive officers’ performance in light of those goals and objectives, and recommending for approval to the Board the executive officers’ compensation levels based on this evaluation.

From time to time, the Compensation Committee may seek input and recommendations from the Chief Executive Officer regarding the compensation of other executive officers; however, the Chief Executive Officer is not present during voting or deliberations on his compensation.

Our Compensation Committee engaged Aon’s Human Capital Solutions practice, a division of Aon PLC (“Aon”), otherwise known as McLagan, as its executive compensation consultant beginning during fiscal year 2022. In this capacity, Aon advised the Compensation Committee on the structure and design of our executive compensation program, including the amount and mix of compensation for fiscal years 2022, 2023, 2024, and 2025, on the Company’s comparative peer group, and director compensation.

Market Analysis

Our peer group was selected based on industry relevancy with revenue and market capitalization metrics utilized to ensure appropriate size comparisons. The peer group approved and used by the Compensation Committee during fiscal year 2025 was made up of these 16 companies:

Atlanticus Holding Corporation AvidXchange Holdings, Inc. Bakkt Holdings, Inc. Cardlytics, Inc. Cass Information Systems, Inc. CoreCard Corporation CPI Card Group, Inc. Flywire Corporation i3 Verticals, Inc. International Money Express, Inc. PAR Technology Corporation PaySign, Inc. Priority Technology Holdings, Inc. Repay Holdings Corporation Sezzle, Inc. Usio, Inc.

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Compensation Discussion & Analysis

Fiscal Year 2025 Executive Compensation

The summary below represents the Company’s 2025 executive compensation overview. See “Executive Officer Employment Arrangements on page 58 for more information.

Base Salary

NEO			Fiscal 2025 Beginning-of-Year Annual Base Salary			Fiscal 2025 End-of-Year Annual Base Salary			% Increase
Mr. Venkatesan			$450,000			$450,000			—
Mr. Stewart			$400,000			$416,000			4.00%
Mr. Dumbrell			$400,000			$416,000			4.00%
Mr. Singal			$362,250			$373,115			3.00%
Mrs. Novoseletsky			$325,000			$350,000			8.00%

Base salary is the fixed component of our NEOs’ annual cash compensation and is set with the goal of attracting and retaining talented executives and adequately compensating and rewarding them for services rendered during the fiscal year. The Compensation Committee reviews our NEOs’ base salaries on an annual basis. Base salaries are intended to reflect an individual’s level of responsibility and performance; however, the Compensation Committee also considers changes in duties and responsibilities, our business and financial results, and its knowledge of market practices in setting and adjusting base salaries.

2026 Proxy Statement 51

Compensation Discussion & Analysis

Annual Bonus

Performance-based annual cash bonuses based on achievement of pre-established performance goals provide NEOs with an opportunity to receive additional cash compensation based on their performance and Company results, including the achievement of pre-determined Company and/or individual performance goals. Although the Compensation Committee intends that our annual bonus program should primarily rely on pre-established performance metrics and goals, the Compensation Committee also retains flexibility to include discretionary elements in our program so that the program may be adapted to adequately suit its retentive purpose and reflect performance that may not be adequately captured in pre-established, objective metrics.

Annual bonuses for fiscal year 2025 were awarded based on the achievement of predetermined corporate goals and the Board of Directors discretionary evaluation (discretion made up 15% of the predetermined corporate goals). The corporate goals were based on the Company’s Adjusted EBITDA (40%), Revenue (25%), and Monthly Recurring Revenue Growth (20%), as detailed in the table below:

			Weight			Rationale
Adjusted EBITDA ($)			40%			These metrics appropriately incentivized our NEOs to achieve sustainable growth in fiscal year 2025, while setting challenging goals that, if achieved, would deliver value to our shareholders.
Revenue ($)			25%
Monthly Recurring Revenue Growth (%)			20%
Board Discretion (%)			15%			-

Adjusted EBITDA (40%) x Revenue (25%) x Monthly Recurring Revenue Growth (20%) x Board Discretion (15%) = Annual Bonus Payout

See “Executive Officer Employment Arrangements” on page 58 for more information.

Achievement below the Minimum level as established in the below table would result in a “Percent Achieved” of 0% for the applicable metric. Achievement at the Target level would result in a “Percent Achieved” of 100% for the applicable metric. And achievement at the Maximum level would result in a “Percent Achieved” of 130% for the applicable metric. Each metric was capped at a “Percent Achieved” of 130%. Payouts are interpolated on a linear basis for achievement between the levels set forth in the table. The Compensation Committee selected the Adjusted EBITDA, Revenue, and Monthly Recurring Revenue Growth (the increase in revenue generated from subscription services during the fiscal year) metrics because it believed that these metrics appropriately incentivized our NEOs to achieve sustainable growth in fiscal year 2025, while setting challenging goals that, if achieved, would deliver value to our shareholders. Adjusted EBITDA is a non-GAAP financial measure which is not required by or defined under GAAP. We use this non-GAAP financial measure for financial and operational decision-making purposes and as a means to evaluate period-to-period comparisons, which we believe makes it appropriate to use for our incentive compensation plans. We define Adjusted EBITDA as U.S. GAAP net income before (i) interest income on cash and leases, (ii) interest expense on debt and sales tax reserves, (iii) income tax provision, (iv) depreciation, (v) amortization, (vi) stock-based compensation expense, (vii) fees and charges, net of reimbursement from insurance proceeds, that were incurred in connection with the 2019 Investigation and financial statement restatement activities as well as proxy solicitation costs that are not indicative of our core operations, (viii) one-time project expense, one-time severance expenses, and infrequent integration and acquisition expense, and (ix) certain other significant infrequent or unusual losses and gains that are not indicative of our core operations including asset impairment charges, and gain on extinguishment of debt.

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Compensation Discussion & Analysis

Financial Goals and Achievement

Based on the actual achievement of each metric in fiscal year 2025 described below, the Compensation Committee calculated an overall achievement on the fiscal 2025 corporate goals of 71.8%, as detailed in table below:

Performance Metric

Minimum

Target

Maximum

Percent Achieved

Weighting

Weighted Percent Achieved

Adjusted EBITDA ($)

93.4%

37.4%

Revenue ($)

0.00%

0.00%

Monthly Recurring Revenue Growth (%)

82.2%

16.4%

Board Discretion (%)

Not applicable

Not applicable

Not applicable

Not applicable

18.0%

Total Corporate Percent Achieved

71.8%

No personal achievement levels were determined for each of our NEO’s in fiscal year 2025 as each NEO’s annual target bonus opportunity is equal to a percentage of their base salary, based on the achievement of corporate performance goals. The individual performance goals for each of our NEOs were primarily focused on projects and initiatives within the functional areas of each NEO to support the accomplishment of corporate goals. For fiscal 2025, the Board approved 120% payout on the board discretionary target.

2026 Proxy Statement 53

Compensation Discussion & Analysis

Fiscal Year 2025 Annual Bonuses

Based on the results achieved above, fiscal year 2025 bonuses earned by each of our NEOs we calculated as set forth in the below table (and in the “Summary Compensation Table” below).

Name			Weight of Corporate Portion			Total Percentage Achieved (A)			Target Bonus (B)			Fiscal 2025 Annual Bonus (A x B)
Ravi Venkatesan			100%			71.8%			450,000			323,100
Scott Stewart			100%			71.8%			208,000			149,344
Jeffrey Dumbrell			100%			71.8%			208,000			149,344
Gaurav Singal			100%			71.8%			186,559			133,949
Anna Novoseletsky			100%			71.8%			175,500			125,650

Equity Awards

Our equity awards to our NEOs primarily reflect initial awards in connection with hires and promotions, as opposed to awards granted under a general annual program.

			Rationale
Stock Options			We believe stock options motivate executives to build long-term shareholder value and help the Company to retain executive talent.
Restricted Stock Units (RSUs)			We believe RSUs provide an appropriate focus on NEO retention and establish strong alignment with long-term stockholder interests through performance-based payouts, and further align our long-term incentive program to with the companies in our peer group.

As described above, our Compensation Committee believes that equity awards are an essential component of an effective compensation program, because they provide a direct link between our shareholders’ interests and our employees, executive officers, directors, and advisors. Our Compensation Committee is therefore focused on emphasizing the importance of equity compensation awards in setting executive compensation. Each NEO’s outstanding equity awards are described in further on the following page.

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Compensation Discussion & Analysis

Equity Awards Granting

Ravi Venkatesan

Fiscal Year			Grant
2023			•On August 11, 2022, Mr. Venkatesan was awarded a grant of 12,011 RSUs, which vest in three equal installments on each of anniversary of the grant date, generally subject to Mr. Venkatesan’s continued employment through each such vesting date. •In connection with his appointment to Chief Executive Officer, Mr. Venkatesan was granted the option to purchase 800,000 options pursuant to the Company’s 2018 Equity Incentive Plan, to be vested equally on the first four anniversaries of October 1, 2022, which are subject to the terms of the award agreement and contingent on the approval of additional shares in the Second Amendment to the Company’s 2018 Equity Incentive Plan.
2024			•On August 4, 2023,Mr. Venkatesan was awarded a grant of 32,904 RSUs, which vest in three equal installments on each of anniversary of the grant date, generally subject to Mr. Venkatesan’s continued employment through each such vesting date.
2025			•On September 20, 2024, Mr. Venkatesan was awarded a grant of 26,745 RSUs, which vest in three equal installments on each of anniversary the grant date, generally subject to Mr. Venkatesan’s continued employment through each such vesting date.

Scott Stewart

Fiscal Year			Grant
2023			•On August 11, 2022, Mr. Stewart was awarded a grant of 11,260 RSUs and 225,000 options, which each vest in three equal installments on each of anniversary of the grant date, generally subject to Mr. Stewart’s continued employment through each such vesting date.
2024			•On August 4, 2023, Mr. Stewart was awarded a grant of 16,952 RSUs, which vest in three equal installments on each of anniversary of the grant date, generally subject to Mr. Stewart’s continued employment through each such vesting date.
2025			•On August 2, 2024, Mr. Stewart was awarded a grant of 37,500 RSUs, which vest in three equal installments on each of anniversary of the grant date, generally subject to Mr. Stewart’s continued employment through each such vesting date. •On September 20, 2024, Mr. Stewart was awarded a grant of 14,264 RSUs, which vest in three equal installments on each of anniversary of the grant date, generally subject to Mr. Stewart’s continued employment through each such vesting date.

2026 Proxy Statement 57

Compensation Discussion & Analysis

Jeff Dumbrell

Fiscal Year			Grant
2023			•On August 12, 2022, Mr. Dumbrell was awarded a grant of 11,260 RSUs and 225,000 options, which each vest in three equal installments on each of anniversary of the grant date, generally subject to Mr. Dumbrell’s continued employment through each such vesting date.
2024			•On August 4, 2023, Mr. Dumbrell was awarded a grant of 16,952 RSUs, which vest in three equal installments on each of anniversary of the grant date, generally subject to Mr. Dumbrell’s continued employment through each such vesting date.
2025			•On August 12, 2024, Mr. Dumbrell was awarded a grant of 37,500 RSUs which vest in three equal installments on each of anniversary of the grant date, generally subject to Mr. Dumbrell’s continued employment through each such vesting date. •On September 20, 2024, Mr. Dumbrell was awarded a grant of 14,264 RSUs, which vest in three equal installments on each of anniversary of the grant date, generally subject to Mr. Dumbrell’s continued employment through each such vesting date.

Gaurav Singal

Year			Grant
2023			•In connection with our hiring of Mr. Singal as our Chief Technology Officer, Mr. Singal was awarded an initial grant of 200,000 stock options on October 27, 2022 with an exercise price of $3.27 per share, which are eligible to vest as follows: eligible to vest in three equal annual installments on the first three anniversaries of the October 27, 2022 dates and in each case subject to Mr. Singal’s continued employment through the applicable vesting date. Mr. Singal resigned from the Company effective October 7, 2025, and as such will not receive the third installment of his annual vesting.
2024			•On August 4, 2023, Mr. Singal was awarded a grant of 15,355 RSUs, which vest in three equal installments on each of anniversary of the grant date, generally subject to Mr. Singal’s continued employment through each such vesting date. Mr. Singal resigned from the Company effective October 7, 2025, and as such will not receive the third installment of his annual vesting.
2025			•On September 20, 2024, Mr. Singal was awarded a grant of 12,198 RSUs, which vest in three equal installments on each of anniversary of the grant date, generally subject to Mr. Singal’s continued employment through each such vesting date. Mr. Singal resigned from the Company effective October 7, 2025, and as such will not receive the second and third installments of his annual vesting.

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Compensation Discussion & Analysis

Anna Novoseletsky

Year			Grant
2024			•In connection with our hiring of Ms. Novoseletsky as our Chief Legal and Compliance Officer, Ms. Novoseletsky was awarded an initial grant of 100,000 stock options on January 24, 2023, with an exercise price of $5.19 per share, which are eligible to vest as follows: eligible to vest in three equal annual installments on the first three anniversaries of the January 24, 2023 dates and in each case subject to Ms. Novoseletsky’s continued employment through the applicable vesting date. •On August 4, 2023, Ms. Novoseletsky was awarded a grant of 14,258 RSUs, which vest in three equal installments on each of anniversary of the grant date, generally subject to Mrs. Novoseletsky’s continued employment through each such vesting date.
2025			•On September 20, 2024, Ms. Novoseletsky was awarded a grant of 11,589 RSUs, which vest in three equal installments on each of anniversary of the grant date, generally subject to Ms. Novoseletsky’s continued employment through each such vesting date.

2026 Proxy Statement 57

Compensation Discussion & Analysis

Executive Perquisites and Other Benefits

Perquisites do not make up a significant portion of NEO compensation. Our NEOs are generally entitled to participate in the health care coverage, group insurance, and other employee benefits (e.g., 401(k) plan) broadly available to our other employees.

Executive Officer Employment Arrangements

Our NEOs are party to employment arrangements or offer letters with us. Certain of these arrangements provide our NEOs with severance protection in the case of a termination without “cause” or, in certain cases, a resignation for “good reason,” which in certain cases is enhanced if such termination occurs in connection with a “change of control.” The Compensation Committee believes that a market level of severance protection allows our NEOs to focus on performing their day-to-day tasks and enhancing value for our shareholders without fearing a loss of financial security as a result of a termination (or constructive termination). These employment arrangements are described in further detail below; for more information, please also see the “Summary Compensation Table” on page 65 and the discussion of “Potential Payments upon Termination or Change of Control” on page 65.

Venkatesan Employment Agreement

Mr. Venkatesan entered into an offer letter with us in connection with this appointment as Chief Executive Officer, amending in part the Original Venkatesan Employment Agreement, to be effective as of September 30, 2022 (the “Promotion Letter” and together with the Original Venkatesan Employment Agreement, the “Venkatesan Employment Agreement”). Pursuant to the Promotion Letter, Mr. Venkatesan’s initial annual base salary was set at $450,000, his annual incentive bonus target is 100% of his base salary, and beginning with the fiscal year ending June 30, 2023, his annual equity grant has a target of 50% of his base salary.

If Mr. Venkatesan is terminated by us without “cause,” or resigns his employment for “good reason,” then, subject to his execution of a release of claims and continued compliance with the covenants in his employment agreement, Mr. Venkatesan is eligible to receive a severance package consisting of 6 months of continued base salary and up to a 6-month COBRA subsidy. However, if such termination occurs within 24 months following a “change of control,” then Mr. Venkatesan will instead be provided a lump sum payment equal to his base salary plus last annual bonus paid in the fiscal year completed prior to such termination. Under the Venkatesan Employment Agreement, if Mr. Venkatesan becomes entitled to receive payments or benefits that would be subject to the excise tax under Section 4999 of the Internal Revenue Code of 1986, as amended, the payments and benefits would be reduced such that the excise tax does not apply, unless Mr. Venkatesan would be better off on an after-tax basis receiving all of the payments and benefits and paying the applicable excise tax.

The Venkatesan Employment Agreement contains customary restrictive covenants, including perpetual confidentiality, non-disparagement, and intellectual property covenants, as a well as a non-compete, non-solicit of customers and suppliers, and non-solicit of employees (including a no-hire) that each apply during employment and for two years following any termination.

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Compensation Discussion & Analysis

Stewart Offer Letter

Mr. Stewart entered into an offer letter with us in connection with his appointment as our Chief Accounting Officer effective as of September 15, 2020. In connection with his appointment as our Chief Financial Officer, the Company entered into an employment agreement with Mr. Stewart effective February 4, 2022 pursuant to which he will receive an initial annual base salary of $360,000 and be eligible to earn an annual incentive bonus with a target opportunity equal to 50% of his base salary pursuant to the terms of the Company’s annual incentive plan.

If Mr. Stewart is terminated by us without “cause,” or resigns his employment for “good reason,” then, subject to his execution of a release of claims and continued compliance with the covenants in his employment agreement, Mr. Stewart is eligible to receive a severance package consisting of 6 months of continued base salary and up to a 6-month COBRA subsidy. However, if such termination occurs within 24 months following a “change of control,” then Mr. Stewart will instead be provided a lump sum payment equal to his base salary plus last annual bonus paid in the fiscal year completed prior to such termination. Under Mr. Stewart’s employment agreement, if Mr. Stewart becomes entitled to receive payments or benefits that would be subject to the excise tax under Section 4999 of the Internal Revenue Code of 1986, as amended, the payments and benefits would be reduced such that the excise tax does not apply, unless Mr. Stewart would be better off on an after-tax basis receiving all of the payments and benefits and paying the applicable excise tax.

Mr. Stewart’s employment agreement contains customary restrictive covenants, including perpetual confidentiality, non-disparagement, and intellectual property covenants, as a well as a non-compete, non-solicit of customers and suppliers, and non-solicit of employees (including a no-hire) that each apply during employment and for two years following any termination.

Dumbrell Offer Letter

Mr. Dumbrell entered into an offer letter with us in connection with his appointment as our Chief Revenue Officer effective as of December 22, 2021 pursuant to which he will receive an initial annual base salary of $360,000 and be eligible to earn an annual incentive bonus with a target opportunity equal to 50% of his base salary pursuant to the terms of the Company’s annual incentive plan.

If Mr. Dumbrell is terminated by us without “cause,” and subject to his execution of a general release of claims and separation agreement, Mr. Dumbrell is eligible to receive a severance package consisting of 6 months of continued base salary.

Mr. Dumbrell’s offer letter contains customary restrictive covenants, including perpetual confidentiality, non-disparagement, and intellectual property covenants, as a well as a non-solicit of customers and suppliers, and non-solicit of employees (including a no-hire) that each apply during employment and during any severance period following any termination.

2026 Proxy Statement 59

Compensation Discussion & Analysis

Singal Offer Letter

Mr. Singal entered into an offer letter with us in connection with his appointment as our Chief Technology Officer effective as of October 27, 2022 pursuant to which he will receive an initial annual base salary of $350,000 and be eligible to earn an annual incentive bonus with a target opportunity equal to 50% of his base salary pursuant to the terms of the Company’s annual incentive plan, and pro-rated from the effective date through the end of the fiscal year 2023.

Pursuant to the terms of Mr. Singal’s employment agreement, if Mr. Singal was terminated by us without “cause,” and subject to his execution of a general release of claims and separation agreement, Mr. Singal would be eligible to receive a severance package consisting of 6 months of continued base salary over a six month period in accordance with CTLP’s regular employee practices and would be subject to standard and customary payroll deductions.

Mr. Singal resigned from the Company following the end of the Company’s fiscal year, effective as of October 7, 2025. Mr. Singal was ineligible to receive any severance payments in connection with his resignation.

Novoseletsky Offer Letter

Ms. Novoseletsky entered into an offer letter with us in connection with her appointment as our Chief Legal and Compliance Officer effective as of January 17, 2023 pursuant to which she will receive an initial annual base salary of $325,000 and be eligible to earn an annual incentive bonus with a target opportunity equal to 50% of her base salary pursuant to the terms of the Company’s annual incentive plan, and pro-rated from the effective date through the end of the fiscal year 2023.

If Ms. Novoseletsky is terminated by us without “cause,” and subject to her execution of a general release of claims and separation agreement, Ms. Novoseletsky is eligible to receive a severance package consisting of 6 months of continued base salary over a six month period in accordance with CTLP’s regular employee practices and would be subject to standard and customary payroll deductions.

Compensation Policies and Practices

Stock Ownership Guidelines

As described above, the Compensation Committee believes that equity ownership in the Company by our executive officers is essential to increasing shareholder alignment. The Company’s Stock Ownership Guidelines support this belief by providing that the Chief Executive Officer is required to hold Common Stock with a value equal to a multiple of three times his base salary and our Chief Financial Officer and other executive officers are required to hold Common Stock with a value equal to his or her base salary. Each executive officer has five years to satisfy the applicable guideline following his or her appointment as an executive officer. As of the date hereof, each of our NEOs who remain employed with us are in compliance with the policy or are in the grace period for compliance.

For purposes of these guidelines, “shares” include shares owned by the executive officer or by such person’s immediate family members residing in the same household (including shares held in trust for the benefit of the foregoing), and include unvested restricted stock awards (but not unexercised stock options).

60 2026 Proxy Statement

Compensation Discussion & Analysis

Clawback Policy

In October 2023, our Board adopted a new Clawback Policy that complies with Section 10D of the Exchange Act and the new Nasdaq listing standards. Under the policy, which applies to the Company’s current and former Section 16 officers, the Company must recover erroneously awarded incentive-based compensation on a pre-tax basis, subject to very limited exceptions. Recovery is triggered in the event that the Company is required to prepare an accounting restatement that correct errors that are material to previously issued financial statements, as well as restatements that correct errors that are not material to previously issued financial statements but would result in a material misstatement if (a) the errors were left uncorrected in the current report or (b) the error correction was recognized in the current period. The policy does not provide for enforcement discretion by the Board and requires recovery regardless of whether a covered person engaged in any misconduct or is at fault.

Anti-Hedging and Insider Trading Policy

Our Anti-Hedging Policy prohibits our employees, officers, and directors from engaging in any hedging or similar transactions with respect to the Company’s securities, including through the establishment of a short position in the Company’s securities, that are designed to or that may reasonably be expected to have the effect of hedging or offsetting a decrease in the market value of the Company’s securities.

Effective September 2024, we adopted a new Insider Trading policy to adopt industry best practices. Our Insider Trading Policy prohibits employees, officers, and directors who are in possession of material, non-public information about the Company from trading in the Company’s securities, as well as communicating such information to others who might trade on the basis of that information.

Our Anti-Heding and Insider Trading policies can both be found in our Corporate Governance documents at https://cantaloupeinc.gcs-web.com/corporate-governance.

Compensation Committee Report

The Compensation Committee has reviewed and discussed the Compensation Discussion and Analysis included in this proxy statement with the Company’s management. Based upon such review and the related discussions, the Compensation Committee has recommended to the Board that the Compensation Discussion and Analysis be included in this proxy statement.

Compensation Committee

Michael K. Passilla (Chair)

Lisa P. Baird

Douglas Bergeron

The foregoing report and other information provided above regarding the Compensation Committee should not be deemed incorporated by reference by any general statement incorporating by reference this proxy statement into any filing under the Securities Act of 1933, as amended (the “Securities Act”) or the Securities Exchange Act of 1934, as amended (the “Exchange Act”), except to the extent that the Company specifically incorporates this information by reference, and shall not otherwise be deemed filed under the Securities Act or the Exchange Act.

2026 Proxy Statement 61

Executive Compensation Tables and Related Disclosures
Summary Compensation Table

The following table sets forth certain information with respect to compensation paid or accrued by the Company during the fiscal years ended June 30, 2025, 2024, and 2023 to each of our fiscal year NEOs. For further information regarding the Company’s fiscal 2025 compensation program for our NEOs, please refer to the discussion above under “-Elements of Compensation” and “-Executive Employment Agreements.”

(1)In fiscal 2025, this column includes (i) the salary paid to Messrs. Venkatesan, Stewart, Dumbrell, Singal and Ms. Novoseletsky.

(2)Represents bonus amounts accrued as of the respective fiscal year end and paid subsequent to fiscal year end based on respective employment agreements and achievement of corporate targets set by the Board.

(3)The grant date fair value of the stock awards shown in this column are computed in accordance with FASB ASC Topic 718. Please see Note 12 (“Stock Based Compensation Plans”) to the Company’s consolidated financial statements for the fiscal year ending June 30, 2025, as filed on Form 10-K with the SEC on September 8, 2025 for further information on how we compute the value of equity awards, and refer to the discussion above under “Elements of Compensation-Equity Awards” for further information on our equity program.

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Executive Compensation Tables and Related Disclosures

(4)The grant date fair value of the stock option awards shown in this column are computed using a Black-Scholes model for time vesting awards and Monte Carlo simulation model for performance based awards in accordance with FASB ASC Topic 718. Please see Note 12 (“Stock Based Compensation Plans”) to the Company’s consolidated financial statements for the fiscal year ending June 30, 2025, as filed on Form 10-K with the SEC on September 8, 2025 for further information on how we compute the value of equity awards, and refer to the discussion above under "Elements of Compensation-Equity Awards" for further information on our equity program.

(5)Represents matching 401(k) plan contributions for each individual during fiscal 2025, as well as transaction bonuses of $200,000 and $100,000 that were paid to Mr. Stewart and Ms. Novoseletsky, respectively, in connection with the Merger Agreement.

(6)Mr. Dumbrell commenced employment as our Chief Revenue Officer in January 2022.

(7)Mr. Singal resigned from the Company following the Company's fiscal year end, effective as of October 7, 2025.

(8)Ms. Novoseletsky commenced employment as our Chief Legal and Compliance Office and General Counsel in January 2023.

Grants of Plan-Based Awards

The table below summarizes the amounts of awards granted to our NEOs during the fiscal year ended June 30, 2025:

Name			Grant Date			Estimated Future Payouts Under Non-Equity Incentive Plan Awards												Estimated Future Payouts Under Equity Incentive Plan Awards												All Other Stock Awards: Number of Shares of Stock or Units (#)			All Other Option Awards: Number of Securities Underlying Options (#)			Exercise or Base Price of Option Awards $/Sh			Grant Date Fair Value of Stock and Option Awards ($)
						Threshold ($)			Target ($)			Maximum ($)						Threshold (#)			Target (#)			Maximum (#)
Ravi Venkatesan			2025 Annual Bonus			315,000			450,000			585,000						—			—			—						—			—			—			—
			9/20/2024(1)			—			—			—						—			26,745			—						26,745			—			—			172,238
Scott Stewart			2025 Annual Bonus			145,600			208,000			270,400						—			—			—						—			—			—			—
			9/20/2024(1)			—			—			—						—			14,264			—						14,264			—			—			91,860
Jeffrey Dumbrell			2025 Annual Bonus			145,600			208,000			270,400						—			—			—						—			—			—			—
			9/20/2025(1)			—			—			—						—			14,264			—						14,264			—			—			91,860
Gaurav Singal			2024 Annual Bonus			130,951			186,559			270,400						—			—			—						—			—			—			—
			9/20/2025(1)			—			—			—						—			12,918			—						12,918			—			—			82,192
Anna Novoseletsky			2025 Annual Bonus			114,100			163,000			270,400						—			—			—						—			—			—			—
			9/20/2025(1)			—			—			—						—			11,589			—						11,589			—			—			74,633

(1)Restricted stock units granted on September 20, 2024 for each officer, vest in three equal installments on each anniversary of September 20, 2024.

2026 Proxy Statement 63

Executive Compensation Tables and Related Disclosures

Outstanding Equity Awards at Fiscal Year-End

The following table shows information regarding unexercised stock options and unvested equity awards held by our NEOs as of June 30, 2025:

						Option Awards																					Stock Awards
Name						Number of securities underlying unexercised options (#) exercisable			Number of securities underlying unexercised options (#) unexercisable			Equity Incentive Plan Awards: Number of securities underlying unexercised unearned options			Option exercise price ($)						Option expiration date						Number of shares or units of stock that have not vested (#)			Market value of shares or units of stock that have not vested ($)(1)
Ravi Venkatesan(2)						295,500			—			—						$    9.44			12/4/2027						52,684			578,997
						200,000			—			—						$    11.20			11/8/2028						—			—
						400,000			400,000			—						$    3.48			10/1/2029						—			—
Scott Stewart(3)						123,125			—			—						$    8.58			9/17/2027						104,317			1,146,444
						100,000			—			—						$    11.20			11/8/2028						—			—
						173,260			—			—						$    8.02			2/7/2029						—			—
						150,000			75,000			—						$    6.68			8/12/2029						—			—
Jeffrey Dumbrell(4)						197,367			—			33,333						$    8.11			12/22/2028						104,317			1,146,444
						150,000			75,000			—						$    6.68			8/12/2029						—			—
Gaurav Singal(5)						133,333			66,667			—						$    3.27			9/12/2029						23,154			254,462
Anna Novoseletsky(6)						66,666			33,333			—						$    5.19			1/24/2030						21,094			231,823

(1)The market value of outstanding awards of restricted stock and RSUs is calculated using the closing price of our Common Stock on June 30, 2025 ($10.99).

(2)Mr. Venkatesan’s options vested as follows: (i) 50% of Mr. Venkatesan’s 300,000 options were eligible to vest based on Mr. Venkatesan’s continued service in three equal installments on each anniversary of November 4, 2020, and (ii) the remaining 50% are eligible to vested on each of November 4, 2021, November 4, 2022, and November 4, 2023, subject in the case of this clause (ii) to the achievement of applicable performance goals for the fiscal year ending on each such date. See the above discussion under “Equity Awards-Ravi Venkatesan” for further information. Mr. Venkatesan’s remaining awards of 200,000 options were eligible to vest based on Mr. Venkatesan’s continued service in three equal installments on each anniversary of the grant date. For fiscal year 2022 and 2023, 91% and 100% options subject to the achievement of applicable performance goals were vested at the discretion of the Board. Mr. Venkatesan’s awards of 800,000 options are eligible to vest based on Mr. Venkatesan’s continued service in four equal installments on each anniversary of October 1, 2022.

(3)Mr. Stewart’s options vested as follows: (i) 50% of Mr. Stewart’s 125,000 options were eligible to vest based on Mr. Stewart’s continued service in three equal installments on each anniversary of September 15, 2020, and (ii) the remaining 50% were eligible to vest on each of September 15, 2021, September 15, 2022, and September 15, 2023, subject in the case of this clause (ii) to the achievement of applicable performance goals for the fiscal year ending on each such date. See the above discussion under “Equity Awards-Scott Stewart” for further information. Mr. Stewart’s awards of 100,000 options were eligible to vest based on Mr. Stewart’s continued service in three equal installments on each anniversary of the grant date. Mr. Stewart’s options granted on February 7, 2022 vest as follows: (i) 117,000 options were eligible to vest based on Mr. Stewart’s continued service in three equal installments on each anniversary of February 7, 2022, and (ii) the remaining 58,000 were eligible to vest on each of February 1, 2023, February 1, 2024, and February 1, 2025, subject in the case of this clause (ii) to the achievement of applicable performance goals for the fiscal year ending on each such date. For fiscal year 2022 and 2023, 91% and 100% options subject to the achievement of applicable performance goals were vested at the discretion of the Board. Mr. Stewart’s awards of 225,000 options were eligible to vest based on Mr. Stewart’s continued service in three equal installments on each anniversary of August 12, 2022.

(4)Mr. Dumbrell’s options vest as follows: (i) 230,000 options are eligible to vest based on Mr. Dumbrell’s continued service in three equal installments on each anniversary of December 22, 2022, and (ii) the remaining 100,000 options were eligible to vest on each of December 22, 2022, December 22, 2023, and December 22, 2024, subject in the case of this clause (ii) to the achievement of applicable performance goals for the fiscal year ending on each such date. For fiscal year 2022 and 2023, 91% and 100% options subject to the achievement of applicable performance goals were vested at the discretion of the Board. Mr. Dumbrell’s awards of 225,000 options were eligible to vest based on Mr. Dumbrell’s continued service in three equal installments on each anniversary of August 12, 2022.

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(5)Mr. Singal’s options were eligible to vest based on Mr. Singal’s continued service in three equal installments on each anniversary of September 12, 2022. Mr. Singal resigned from the Company following the Company’s fiscal year end, effective as of October 7, 2025.

(6)Ms. Novoseletsky’s options are eligible to vest based on Ms. Novoseletsky’s continued service in three equal installments on each anniversary of January 24, 2023.

Option Exercises and Stock Vested

The following table sets forth information regarding options exercised and shares of common stock acquired upon vesting by our NEOs during the fiscal year ended June 30, 2025:

			Option Awards									Stock Awards
Name			Number of Shares Acquired on Exercise (#)			Value Realized on Exercise ($)						Shares Acquired on Vesting (#)			Value Realized on Vesting ($)
Ravi Venkatesan			—			—						18,323						143,114
Scott Stewart			—			—						11,161						85,340
Jeffrey Dumbrell			—			—						9,405						67,007
Anna Novoseletsky			—			—						5,119						37,983
Gaurav Singal			—			—						4,753						35,267

Potential Payments Upon Termination or Change of Control

In accordance with Item 402(t) of Regulation S-K promulgated under the Securities Act of 1933, as amended, the table below sets forth the amount of payments and benefits that each of our named executive officers would or may receive in connection with the Merger. The amounts reported below are based on various assumptions that may or may not actually occur or be accurate on the relevant date, including assumptions described in the footnotes to the table and the below:

•The effective time of the Merger is October 2, 2025, which is the assumed date of the closing of the Merger solely for the purposes of this disclosure;

•The employment of each of our named executive officers is terminated other than for “cause” or by the named executive officer for “good reason”, in either case, immediately following the assumed effective time of the Merger;

•No named executive officer enters into a rollover agreement;

•Each named executive officer’s base salary remains unchanged from that in effect as of the date of this proxy statement;

•For purposes of the annual bonus payments and Cantaloupe PSUs set forth in the table, achievement is at the target levels of performance; and

•No named executive officer has any payments or benefits that would be “excess parachute payments” pursuant Code Section 280G.

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Messrs. Venkatesan, Stewart, Dumbrell, and Singal, and Ms. Novoseletsky

During fiscal year 2025, each of Messrs. Venkatesan, Stewart, Dumbrell, and Singal and Ms. Novoseletsky were entitled to certain severance payments and benefits upon a termination without “cause,” or, where applicable, a resignation for “good reason,” as further described above under “Executive Employment Agreements.” In addition, under the general terms of our equity award plans, a participating employee is entitled to “double-trigger” accelerated vesting of outstanding equity awards if such employee is terminated by us without “cause,” or, to the extent provided in the employee’s award agreement, if the employee resigns for “good reason,” in each case within 18 months following a “change of control.” The following table summarizes these potential payments and benefits, with all equity estimates based on the closing price of our Common Stock on June 30, 2025 ($11.07) and assuming that the applicable termination event or “change of control” occurred on the last day of fiscal 2025, June 30, 2025:

Named Executive Officer									Cash ($)(1)									Equity ($)(2)									Total ($)
Ravi Venkatesan									1,350,000									1,866,538									3,216,538
Scott Stewart									1,032,000									869,781									1,901,781
Jeffrey Dumbrell									416,000									869,781									1,285,781
Gaurav Singal									373,118									153,776									526,894
Anna Novoseletsky									450,000									340,090									790,090

(1)Cash. Pursuant to each named executive officer’s applicable employment agreement, the named executive officer is entitled to the following:

•If Mr. Venkatesan is terminated by Cantaloupe without cause or resigns for good reason and within 24 months following a “change of control”, then, subject to his execution of a release of claims and continued compliance with the covenants in his employment agreement, Mr. Venkatesan will be provided a lump sum payment equal to his base salary (without giving effect to any reduction that is the basis for any resignation for “good reason”) plus an amount equal to the last annual bonus paid in the fiscal year completed prior to such termination.

•If Mr. Stewart is terminated by Cantaloupe without cause or resigns for good reason within 24 months following a “change of control”, then, subject to his execution of a release of claims and continued compliance with the covenants in his employment agreement, Mr. Stewart will be provided a lump sum payment equal to his base salary (without giving effect to any reduction that is the basis for any resignation for “good reason”) plus an amount equal to the last annual bonus paid in the fiscal year completed prior to such termination.

•If Mr. Dumbrell or Ms. Novoseletsky are terminated by Cantaloupe without cause, and subject to execution of a general release of claims and separation agreement, a severance package consisting of six months of continued base salary.

•If Mr. Singal was terminated by Cantaloupe without cause, and subject to execution of a general release of claims and separation agreement, a severance package consisting of six months of continued base salary. However, Mr. Singal resigned from the Company following the end of the Company’s fiscal year, effective as of October 7, 2025. Mr. Singal was ineligible to receive any severance payments in connection with his resignation.

Severance is “double trigger” for Mr. Venkatesan and Mr. Stewart, while the cash payments received by certain of our named executive officers in connection with the Merger, which are repayable to the Company if the Merger does not occur (the "Transaction Bonuses"), and the annual bonus payments are “single-trigger”. Severance for Mr. Dumbrell, Mr. Singal and Ms. Novoseletsky is not single or double trigger as severance is paid for these named executive officers based on a termination by Cantaloupe without cause and without respect to a change in control.

The following table quantifies each separate form of cash payment included in the aggregate total reported in the “Cash” column.

Named Executive Officer									Severance ($)									Transaction Bonus									2026 Annual Bonuses ($)
Ravi Venkatesan									900,000									-									450,000
Scott Stewart									624,000									200,000									208,000
Jeffrey Dumbrell									208,000									—									208,000
Gaurav Singal(3)									186,559									—									186,559
Anna Novoseletsky									$175,000									100000									175000

(2)Equity. Given the assumptions and treatment of Cantaloupe equity awards, these amounts reflect the cash-out of the Cantaloupe RSUs, Cantaloupe Restricted Stock Awards, Cantaloupe In-the-Money Options and Cantaloupe PSUs.

(3)Mr. Singal resigned from the Company following the end of the Company’s fiscal year, effective as of October 7, 2025. Mr. Singal was ineligible to receive any severance payments in connection with his resignation.

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CEO Pay Ratio Disclosure

As required by SEC rules, we are providing the following information about the relationship of the annualized total compensation of our Chief Executive Officer, Ravi Venkatesan, to that of our median employee. The pay ratio and annual total compensation amount disclosed in this section are reasonable estimates that have been calculated using methodologies and assumptions permitted by SEC rules.

Median Employee Determination

We identified our median employee in fiscal 2025 by calculating the fiscal 2025 cash compensation for all of our employees, excluding our Chief Executive Officer, who were employed by us on June 30, 2025. Cash compensation included all cash salaries, wages, and bonuses paid to each employee during the fiscal year.

Annual Compensation of Median Employee Using Summary Compensation Table Methodology

After identifying the median employee as described above, we calculated annual total compensation for this employee using the same methodology we use in the Summary Compensation Table. The fiscal 2025 compensation for our median employee was $80,000, and our Chief Executive Officer was $957,707.

2025 Pay Ratio

Based on the above information, the estimated ratio of the annual total compensation of our Chief Executive Officer to the median employee is 12:1. The pay ratio reported by other companies may not be comparable to the pay ratio reported above, due to variances in business mix, proportion of seasonal and part-time employees, distribution of employees across geographies, and the wide range of methodologies that the SEC rules allow companies to adopt in calculating this pay ratio.

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Pay Versus Performance

As required by Section 953(a) of the Dodd-Frank Wall Street Reform and Consumer Protection Act of 2010 and Item 402(v) of Regulation S-K, we are providing the following information about the relationship between executive compensation actually paid and certain financial performance of the Company. The following table sets forth information regarding compensation for Mr. Venkatesan, our principal executive officer (PEO), Mr. Feeney, our former principal executive officer, and average compensation related to our other named executive officers versus our Company performance for the past three years.

																											Average Summary Compensation Table Total for Non-PEO NEOs ($)(3)									Average Compensation Actually Paid to Non-PEO NEOs ($)(2)(3)									Value of Initial Fixed $100 Investment based on:
Year									Summary Compensation Table Total for PEO ($)(1)									Compensation Actually Paid to PEO ($)(2)																											Total Shareholder Return ($)(4)									Peer Group Total Shareholder Return ($)(5)																		Net Income ($)(6)									Adjusted EBITDA* ($)(7)
2025									957,707									1,725,357									975,073									1,480,839									56									89																		64,533,000									46,740,000
2024									1,046,238									2,137,587									643,599									1,046,244									56									89																		11,993,000									33,960,000
2023									2,802,535									3,627,663									1,131,882									1,422,254									114									131																		633,000									17,794,000
2022									990,474									(1,989,647)									1,086,222									1,326,797									80									119																		(1,703,000)									9,892,000

Adjusted EBITDA is a non-GAAP financial measure, Please see Appendix A at the end of this Proxy Statement for a reconciliation of Adjusted EBITDA

(1)The dollar amounts reported in the column reflect the amounts of total compensation reported for Mr. Venkatesan and Mr. Feeney, as applicable, for each corresponding year in the “Total” column of the Summary Compensation Table. Mr. Venkatesan was our principal executive officer for the fiscal year ended June 30, 2024 and June 30, 2023, and Mr. Feeney was our principal executive officer for the fiscal year ended June 30, 2022.

(2)Amounts are calculated in accordance with Item 402(v) and do not reflect actual amounts of compensation paid to the PEO and other Non-PEO NEOs. See table below for detail of amounts deducted and added to the Summary Compensation Table figure to calculate compensation actually paid.

									2025																											2024																											2023																											2022
									PEO($)									Average of Non-PEO NEOs($)																		PEO($)									Average of Non-PEO NEOs($)																		PEO($)									Average of Non-PEO NEOs($)																		PEO($)									Average of Non-PEO NEOs($)
Total Compensation as reported on Summary Compensation Table									957,707									975,073																		1,046,238									643,599																		2,802,535									1,131,882																		990,474									1,086,222
Fair value of stock awards reported in Summary Compensation Table									(172,238)									(355,011)																		(244,148)									(117,824)																		(1,936,233)									(669,484)																		(225,000)									(708,513)
Fair value of equity compensation granted in current year - value at year-end									293,660									557,331																		217,166									104,803																		1,951,608									676,690																		120,691									364,374
Change in fair value from end of prior fiscal to end of current fiscal year for awards made in prior fiscal years that were unvested at end of current fiscal year									445,041									219,894																		590,771									174,033																		644,231									94,484																		(2,633,750)									502,510
Change in fair value from end of prior fiscal year to vesting date for awards made in prior fiscal years that vested during current fiscal year									201,187									83,552																		527,560									241,633																		165,523									188,682																		(242,063)									296,817
Fair value as of prior fiscal year-end of awards granted in prior fiscal years that failed to meet applicable vesting conditions during fiscal year									-									-																		-									-																		-									-																		-									(214,613)
Compensation Actually Paid									1,725,357									1,480,839																		2,137,587									1,046,244																		3,627,663									1,422,254																		(1,989,647)									1,326,797

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(3)The dollar amounts reported in the column reflect the average amounts of total compensation reported for our non-PEO NEOs for each corresponding year in the “Total” column of the Summary Compensation Table.

(4)Total shareholder return assumes that $100 was invested on the measurement date in the Company’s common stock and the peer group as set forth in footnote 5 below. The measurement date is established by the market close on the last trading day before the beginning of the Company’s third preceding fiscal year.

(5)The peer group reflects the US Small-Cap Russell 2000® Index, which was used in the Stock Performance Graph included in our Annual Report.

(6)Dollar amounts reported represent the amount of net income reflected in the Company’s audited financial statements for the applicable year

(7)The Company has determined that Adjusted EBITDA from continuing operations is the financial performance measure that, in the Company’s assessment, represents the most important performance measure (that is not otherwise required to be disclosed in the table) used by the Company to link compensation actually paid to the Company’s named executive officers for the most recently completed fiscal year.

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Relationship between “Compensation Actually Paid” and Performance

Below are the graphs showing the relationship of “compensation actually paid” to our CEO and our non-CEO NEOs in fiscal 2022, 2023, 2024 and 2025 to (1) TSR, (2) the Company’s net income and (3) the Company’s Adjusted EBITDA.

Compensation Actually Paid (CAP) vs TSR

n Average CAP to NEOs n CAP to CEO — TSR — Peer Group TSR

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Compensation Actually Paid (CAP) vs Net Income

n Average CAP to NEOs n CAP to CEO — Net Income

Compensation Actually Paid (CAP) vs Adjusted EBITDA

n Average CAP to NEOs n CAP to CEO — Adjusted EBITDA

Listed below are the financial and non-financial performance measures which in our assessment represent the most important financial performance measures we used to link compensation actually paid to our NEOs, for fiscal 2025, to company performance:

•Revenue

•Adjusted EBITDA

•Monthly recurring revenue

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Policies and Practices for Granting Certain Equity Awards

The Board, at the recommendation of the Compensation Committee, approves all equity award grants to our NEOs on or before the grant date. The Compensation Committee’s general practice is to complete its annual executive compensation review and determine performance goals and target compensation for our NEOs, following which they make a recommendation to the Board, which in turn reviews the recommendation and approves equity awards for our NEOs. Accordingly, annual equity awards are typically determined at the first Compensation Committee meeting of the fiscal year and reviewed and approved at the first Board meeting of the fiscal year. These grants are then made effective shortly during a scheduled open trading window. On occasion, the Board may, at the recommendation of the Compensation Committee, grant equity awards outside of our annual grant cycle for new hires, promotions, recognition, retention or other purposes. While the Board has discretionary authority to grant equity awards to our NEOs outside of the cycle described above, neither the Board nor the Compensation Committee take into account material non-public information when determining the timing or terms of equity awards, nor do we time disclosure of material non-public information for the purpose of affecting the value of executive compensation.

During fiscal 2025, the Company did not grant stock options (or similar awards) to any NEO during any period beginning four business days before and ending one business day after the filing of any Company periodic report on Form 10-Q or Form 10-K, or the filing or furnishing of any Company Form 8-K that disclosed any material non-public information.

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Proposal 3
Ratification of Appointment of Independent Registered Public Accountants

Engagement of Deloitte

The Audit and Risk Committee appointed Deloitte to serve as the Company’s independent registered public accounting firm for fiscal year 2026. The shareholders will be asked to ratify this appointment at the Annual Meeting. A representative of Deloitte is expected to be present at the Annual Meeting and will have the opportunity to make a statement, if desired, and is expected to be available to respond to appropriate questions.

The following resolution concerning the appointment of the independent registered public accounting firm will be presented to the shareholders at the Annual Meeting:

RESOLVED, that the appointment by the Audit and Risk Committee of the Board of Directors of the Company of Deloitte, independent registered public accounting firm, to perform independent audit services for the fiscal year ending June 30, 2026 is hereby ratified and approved.

The affirmative vote of a majority of the votes cast by all holders of the issued and outstanding shares of Common Stock and Series A Preferred Stock voting together (with each share of Common Stock entitled to one vote and each share of Series A Preferred Stock entitled to 0.1988 of a vote, with any fractional vote being rounded to the nearest whole number) is required for ratification of this proposal.

The Board of Directors recommends that you vote “FOR” the ratification of the proposal set forth above.

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Audit Matters

Principal Accountant Fees and Services

Audit Fees

Audit fees consisted of fees for the audit of our annual financial statements, review of quarterly financial statements and the audit of internal control over financial reporting, as well as services normally provided in connection with statutory and regulatory filings or engagements, consents and assistance with and reviews of Company documents filed with the Securities and Exchange Commission.

Our independent registered public accounting firm, Deloitte & Touche LLP (“Deloitte”), billed us aggregate fees in the amount of $2,513,152 for the fiscal year ended June 30, 2025 in connection with services rendered. Audit fees by our independent registered public accounting firm, Deloitte, amounted to $2,641,236 in connection with services rendered for the fiscal year ended June 30, 2024.

In connection with BDO USA, P.C. (“BDO”)’s consent to the use of their audit opinion over the years ended June 30, 2022 and June 30, 2023 in our 2024 and 2025 annual financial statements, our former independent registered public accounting firm, BDO, billed us $375,000 and $250,000, respectively.

Audit-Related Fees

Audit-related fees consisted of fees for the audit of the Company’s 401(k) retirement plan, services associated with the merger proxy statements and work paper access reviews for due diligence. Our independent registered public accounting firm, Deloitte, billed us aggregate fees in the amount of $28,228 and $30,000 for the fiscal years ended June 30, 2025 and 2024, respectively for services rendered for the 401(k) retirement plan.

The Company paid $75,000 to our independent registered public accounting firm, Deloitte, for services associated with the merger proxy statements during the fiscal year ended June 30, 2025. The Company paid $50,000 to our former independent registered public accounting firm, BDO, for services associated with the merger proxy statements during the fiscal year ended June 30, 2025.

The Company paid $50,000 to our independent registered public accounting firm, Deloitte, associated with work paper access reviews for due diligence during the fiscal year ended June 30, 2025.

Tax Fees

There were no tax fees billed to us by Deloitte and BDO, during the fiscal years ended June 30, 2025 and 2024.

All Other Fees

There were no fees paid to either firm for the year ended June 30, 2025 and 2024.

Additional Information

The Audit and Risk Committee determined that the provision of services other than audit services by Deloitte was compatible with maintaining Deloitte’s independence.

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Audit and Risk Committee Pre-Approval Policy

The Audit and Risk Committee’s policy is to pre-approve all audit and permissible non-audit services provided by the independent registered public accounting firm on a case-by-case basis. The Audit Committee has the authority to approve all audit engagement fees and terms and pre-approve all audit and permissible non-audit services provided by the Company’s independent registered public accounting firm. For fiscal 2025 and fiscal 2024, all of the fees included under the headings “Tax Fees” and “All Other Fees” above were pre-approved by the Audit Committee.

Report of The Audit and Risk Committee

The Audit and Risk Committee’s (for purposes of this Report of the Audit and Risk Committee, “we,” “us,” or the “Committee”) primary responsibility is to assist the Board in fulfilling its responsibility to oversee and review the quality and integrity of the Company’s financial statements and internal controls over financial reporting, and the independent auditor’s qualifications and independence. Management has the primary responsibility for the preparation of the financial statements and establishing effective internal controls over financial reporting.

In the performance of its oversight function, the Audit and Risk Committee has reviewed and discussed the Company’s audited consolidated financial statements with management. We discussed with Deloitte, the Company’s independent registered public accounting firm, its audit of the Company’s consolidated financial statements and internal controls over financial report. We discussed with Deloitte the overall scope and plans for their audit. We have reviewed and discussed with management its process for preparing its report on its assessment of our internal controls over financial reporting, and at regular intervals we received updates on the status of this process and actions taken by management to respond to issues and deficiencies identified.

We have discussed with Deloitte the matters required to be discussed by the auditors with the Audit and Risk Committee under rules adopted by the Public Company Accounting Oversight Board (the “PCAOB”) and the SEC. We also received written disclosures and the letter from Deloitte regarding its independence as required by applicable requirements of the PCAOB regarding the independent accountant’s communications with the audit and Risk Committee concerning independence, and discussed with Deloitte its independence.

In reliance on the reviews and discussions referred to above, the Audit and Risk Committee recommended to the Board that the audited consolidated financial statements be included in the Company’s Annual Report for the fiscal year ended June 30, 2025 for filing with the SEC. We also evaluated and selected Deloitte as the Company’s independent auditor for the fiscal year ended June 30, 2026, which the shareholders will be asked to ratify at the Annual Meeting.

The Audit and Risk Committee

Shannon Warren (Chair)

Ellen Richey

Anne Smalling

The foregoing report and other information provided above regarding the Audit and Risk Committee should not be deemed incorporated by reference by any general statement incorporating by reference this proxy statement into any filing under the Securities Act or the Exchange Act, except to the extent that the Company specifically incorporates this information by reference, and shall not otherwise be deemed filed under the Securities Act or the Exchange Act.

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Stock Ownership Information
Security Ownership of Certain Beneficial Owners and Management
Common Stock
The following table sets forth, as of September 25, 2025, the beneficial ownership of the common stock of each of the Company’s directors, by the named executive officers included in the Fiscal Year 2025 Summary Compensation Table set forth above, by the Company’s directors, named executive officers and other executive officers as a group, and by the beneficial owners of more than 5% of the common stock. Except as otherwise indicated below, the Company believes that the beneficial owners of the common stock listed below, based on information furnished by such owners, have sole investment and voting power with respect to such shares, subject to community property laws where applicable:

Name of Beneficial Owner (1)			Number of Shares of Common Stock Beneficially Owned			Percent of Class(2)
Douglas G. Bergeron (3)			1,152,559			1.6%
Lisa P. Baird			217,319			*
Jeffrey Dumbrell			609,142			*
Ian Harris			275,375			*
Jacob Lamm			198,319			*
Anna Novoseletsky			76,172			*
Michael K. Passilla			198,319			*
Ellen Richey			198,319			*
Gaurav Singal			25,989			*
Anne M. Smalling			198,319			*
Scott Stewart			626,788			*
Ravi Venkatesan			1,226,561			1.7%
Shannon S. Warren			198,319			*
All directors and executive officers as a group (13 persons)			5,201, 500			7.1%

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Name and Address of Beneficial Owner			Number of Shares of Common Stock Beneficially Owned						Percent of Class
Hudson Executive Capital LP			9,319,372			(4)			12.7%
BlackRock, Inc.			4,423,558			(5)			6.0%
Oakland Hills BV			3,667,000			(6)			5.0%
All 5% Shareholders			17,409,930						23.7%

*    Less than one percent (1%)

(1)Beneficial ownership is determined in accordance with the rules of the Securities and Exchange Commission and derives from either voting or dispositive power with respect to securities. Shares of Common Stock issuable upon conversion of the Series A Preferred Stock, or shares of Common Stock issuable upon exercise of options currently exercisable, or exercisable within 60 days of September 25, 2025, are deemed to be beneficially owned for purposes hereof.

(2)The percentage of stock beneficially owned is based on 73,691,758 common shares outstanding as of September 25, 2025.

(3)The total above also includes shares held in a trust account to which Mr. Bergeron controls and has voting power with respect to such shares. In addition to the shares set forth above, Mr. Bergeron also has an economic interest in a Hudson affiliated fund that beneficially owns shares of Cantaloupe’s common stock. Mr. Bergeron does not have investment discretion or voting power with respect to such shares and disclaims beneficial ownership of such shares except to the extent of his pecuniary interest therein.

(4)Based upon a Schedule 13D filed on June 16, 2025 with the SEC, each of the following persons has shared voting and dispositive power over 9,319,372 shares of common stock: Hudson, which serves as investment advisor to certain affiliated investment funds which have the right to receive dividends from, and the proceeds from the sale of, the 9,319,372 shares; HEC Management GP LLC, which is the general partner of Hudson; and Douglas L. Braunstein, who is the managing partner of Hudson and the managing member of HEC Management GP LLC. Mr. Braunstein’s total includes 20,212 shares of common stock directly owned by him. The business address of each of the foregoing persons is Hudson Executive Capital LP c/o White & Case LLP, 1221 6th Avenue New York, NY, 10020.

(5)Based upon a Schedule 13G filed on January 29, 2024 with the SEC, each of the following subsidiaries of BlackRock, Inc. have the right to receive or the power to direct the receipt of dividends from, or the proceeds from the sale of, the 4,423,558 shares: Aperio Group, LLC, BlackRock Advisors, LLC, BlackRock Asset Management Canada Limited, BlackRock Fund Advisors, BlackRock Asset Management Ireland Limited, BlackRock Institutional Trust Company, NA, BlackRock Financial Management, Inc., BlackRock Fund Managers Ltd, BlackRock Asset Management Schweiz AG, and BlackRock Investment Management, LLC. The address of BlackRock, Inc. is 55 East 52nd Street, New York, NY 10055.

(6)Based upon a Schedule 13G filed on February 5, 2025 with the SEC, Oakland Hills BV directly owns 3,667,000 shares of common stock. Malabar Hill NV, is the statutory director of Oakland Hills BV, and Mr. R. Derksen, and Mrs. E.G.J. Labas are each statutory directors of Malabar Hill NV and, acting individually, each have voting and dispositive power over the shares held by Oakland Hills BV. Prior to his death on November 21, 2022, Drs. Frederick Harald Fentener van Vlissingen was statutory director of Malabar Hill NV. As the executor of the estate of Drs. van Vlissingen, Mrs. Eveline Muller has the ability to appoint and remove statutory directors of Malabar Hill NV and may be deemed a beneficial owner of the shares reported on the Schedule 13G. The principal business address of each of the foregoing persons is Albert Hahnplantsoen 23, 1077 BM, Amsterdam, The Netherlands.

Preferred Stock

As of October 10, 2025, there were 385,282 shares of Series A Preferred Stock outstanding. None of the Company’s directors or executive officers beneficially own shares of Series A Preferred Stock, and to the Company’s knowledge, there are no beneficial owners of more than 5% of the Series A Preferred Stock.

2026 Proxy Statement 77

Executive Compensation Tables and Related Disclosures

Delinquent Section 16(a) Reports

Section 16(a) of the Securities Exchange Act of 1934 requires the Company’s officers and directors, and persons who own more than ten percent of a registered class of the Company’s equity securities, to file with the Securities and Exchange Commission reports of ownership of Company securities and changes in reported ownership. Based on a review of reports filed with the SEC, or written representations from reporting persons that all reportable transaction were reported, the Company believes that during the fiscal year ended June 30, 2025, the Company’s officers, directors and greater than ten percent owners timely filed all reports they were required to file under Section 16(a), except reports filed by Messrs. Grachek, Stewart, Venkatesan, Singal and Dumbrell and Ms. Novoseletsky regarding historic grants of RSUs, which were similarly filed late as a result of an administrative error.

78 2026 Proxy Statement

Questions and Answers About the Proxy Materials and Annual Meeting

Why am I receiving a notice regarding the availability of proxy materials on the Internet?

You are receiving a Notice because, as of the close of business on September 25, 2025, you owned shares of Common Stock, or series A convertible preferred stock, no par value (“Series A Preferred Stock”), of the Company. We are providing access to our proxy materials over the Internet pursuant to the Securities and Exchange Commission’s notice and access rules. The Notice will indicate how to access our proxy statement on the Internet and will include instructions on how you can receive a paper copy of the annual meeting materials, including the notice of annual meeting, proxy statement and proxy card.

When you execute your proxy, you appoint Scott Stewart and Anna Novoseletsky each as your representatives at the annual meeting. Mr. Stewart and/or Ms. Novoseletsky will vote your shares at the meeting as you have instructed them on the proxy card. If an issue comes up for vote at the meeting that is not on the proxy card, Mr. Stewart and/or Ms. Novoseletsky will vote your shares, under your proxy, in accordance with their best judgment.

How can I attend the annual meeting?

We look forward to continuing to provide expanded access, improved communication, and cost savings for the Company and our shareholders by holding our Annual Meeting entirely online. We believe a live virtual meeting enables increased shareholder attendance and participation and is an efficient use of resources for our shareholders and the Company. Accordingly, the 2026 Annual Meeting of Shareholders will be held in live virtual format. Only such shareholders as of the close of business on September 25, 2025, their proxy holders, and our invited guests may attend the 2026 Annual Meeting of Shareholders. To participate in the virtual annual meeting, visit www.virtualshareholdermeeting.com/CTLP2025 and log in using the 16-digit control number printed in the box marked by the arrow on your proxy card. If you encounter any technical difficulties with the virtual meeting platform on the meeting day, technical support phone numbers will be posted on the virtual meeting log-in page.

What am I voting on?

At the Annual Meeting, we will ask holders of our Common Stock or Series A Preferred Stock to consider and vote upon the following items:

1.Election of Directors

The election of nine directors to serve until the 2026 Annual Meeting of Shareholders.

2.Advisory Vote on the Compensation of our Named Executive Officers

A “Say-on-Pay” advisory vote on the approval of the compensation of the Company’s named executive officers.

3.Ratification of Appointment of Independent Registered Public Accounting Firm

Ratification of the appointment of Deloitte as the Company’s independent registered public accounting firm for the fiscal year ending June 30, 2026.

2026 Proxy Statement 79

Questions and Answers About the Proxy Materials and Annual Meeting

Who is entitled to vote?

Shareholders as of the close of business on September 25, 2025 are entitled to vote. This is referred to as the record date. Each share of Common Stock is entitled to one vote and each share of Series A Preferred Stock is entitled to 0.1988 of a vote on all matters to come before the Annual Meeting, with any fractional vote being rounded to the nearest whole number.

How do I vote my shares without attending the meeting?

If you are a shareholder of record as of the record date for the Annual Meeting, you may vote by granting a proxy. For shares held in street name, you may vote by submitting voting instructions to your broker or nominee. In most circumstances, you may vote:

By Internet or Telephone - If you have internet or telephone access, you may submit your proxy by following the voting instructions in the Notice of Annual Meeting no later than 11:59 p.m., ET, on November 18, 2025. If you vote by internet or telephone, you need not return your proxy card.

By Mail - If you received a paper copy of this proxy statement, you may vote by mail by signing, dating and mailing your proxy card in the envelope provided. You should sign your name exactly as it appears on the proxy card. If you are signing in a representative capacity (for example, as guardian, executor, trustee, custodian, or attorney or an officer of a corporation), you should indicate your name and title or capacity.

How do I vote my shares virtually at the meeting?

If you are a shareholder of record as of the record date for the Annual Meeting, you can participate in the Annual Meeting live online at www.virtualshareholdermeeting.com/CTLP2026. The webcast will start on November 19, 2025 at 11:00 a.m., ET. You may vote and submit questions while attending the Annual Meeting online. You will need the sixteen-digit control number included on your Notice, on your proxy card or on the instructions that accompanied your proxy materials in order to be able to enter the meeting.

Street name shareholders must provide specific instructions on how to vote your shares by completing and returning the voting instruction form provided by your bank, broker, trustee or other nominee. Even if you plan to attend the virtual meeting, we encourage you to vote in advance by internet, telephone or mail so that your vote will be counted in the event you are unable to attend.

Are voting procedures different if I hold my shares in the name of a broker, bank or other nominee?

If your shares are held in “street name” through a broker, bank or other nominee, please refer to the instructions they provide regarding how to vote your shares or to revoke your voting instructions. If you hold your shares in the name of a broker, bank or other nominee, the availability of telephone and Internet voting depends on their voting processes. Street name holders may vote in person only if they have a legal proxy as described above.

80 2026 Proxy Statement

Questions and Answers About the Proxy Materials and Annual Meeting

How many votes do you need to hold the meeting?

As of September 25, 2025, the record date for the Annual Meeting, there were 73,391,758 shares of Common Stock and 385,282 shares of Series A Preferred Stock of the Company. Only holders of Common Stock or Series A Preferred Stock of record at the close of business on September 25, 2025 will be entitled to vote. Each share of Common Stock is entitled to one vote and each share of Series A Preferred Stock is entitled to 0.1988 of a vote on all matters to come before the Annual Meeting, with any fractional vote being rounded to the nearest whole number. The number of votes to which each share of Series A Preferred Stock is entitled is equal to the votes attributable to that number of shares of Common Stock into which each share of Series A Preferred Stock is convertible. A majority of the Company’s outstanding shares as of the record date must be present at the meeting either in person or by proxy in order to hold the meeting and conduct business. This is called a quorum.

Your shares will be counted as present at the meeting if you:

•vote via the Internet or by telephone, if available;

•properly submit a proxy (even if you do not provide voting instructions); or

•attend the virtual meeting and vote electronically.

What does it mean if I receive more than one Notice?

It means that you have multiple accounts at the transfer agent and/or with a broker, bank or other nominee. Please vote all proxies to ensure that all your shares are represented at the meeting. In the future, you may wish to consolidate as many of your transfer agent accounts or accounts with brokers, banks or other nominees as possible under the same name and address for better customer service.

What if I change my mind after I return my proxy?

You may revoke your proxy and change your vote at any time before the polls close at the meeting. You may do this by:

•sending written notice to the Corporate Secretary at 101 Lindenwood Drive, Suite 120, Malvern, Pennsylvania 19355 so that it is received prior to November 19, 2025;

•voting again over the Internet or via telephone, if available, prior to 11:59 p.m., ET, on November 18, 2025;

•signing another proxy with a later date and sending it so that it is received prior to November 17, 2025; or

•attending the virtual meeting and voting electronically.

2026 Proxy Statement 81

How are votes counted?

Shares of Common Stock or Series A Preferred Stock represented by properly executed proxy cards, or voted by proxy over the Internet or telephone, and received in time for the Annual Meeting will be voted in accordance with the instructions specified in the proxies. Any proxy not specifying to the contrary will be voted (1) for the nine Board nominees in Proposal 1; (2) in favor of the ratification of Proposal 2; and (3) in favor of the recommendation in Proposal 3. If, for any unforeseen reason, any of our nominees is not available as a candidate for director, the persons named as proxy holders will vote your proxy for another candidate or other candidates nominated by our Board.

How may I vote for each proposal?

With respect to each proposal, you may:

•vote FOR the proposal;

•vote AGAINST the proposal; or

•ABSTAIN from voting

How many votes are needed for each proposal?

Proposal Number

Item

Votes Required for Approval or Ratification

Effect of Abstentions(2)

Effect of Broker Non-Votes(3)

Board Voting Recommendation

1

Election of Nine Directors

Majority of votes cast(1)

None

None

FOR each nominee

2

Approve, on an advisory basis, the compensation of named executive officers

Majority of votes cast

None

None

FOR

3

Ratify the Appointment of Deloitte

Majority of votes cast

None

Not Applicable(4)

FOR

(1)Directors will be elected by a majority of the votes cast by all holders of the issued and outstanding shares of Common Stock and Series A Preferred Stock voting together (with each share of Common Stock entitled to one vote, and each share of Series A Preferred Stock entitled to 0.1988 of a vote, with any fractional vote being rounded to the nearest whole number). Pursuant to the Company’s Director Majority Voting Policy, any nominee for director in an uncontested election who receives a greater number of votes “against” his or her election than votes “for” such election shall promptly submit to the Board a letter of resignation to the Secretary of the Company.

(2)Abstentions with respect to a proposal are counted for purposes of establishing a quorum.

(3)Broker non-votes refer to shares of stock held in street name with regard to which the broker or other nominee holding them indicates on a proxy that the broker has not received instructions from the beneficial owner to vote those shares in a particular manner on a proposal for which the broker or other nominee does not have discretion to vote without specific instructions from the beneficial owner. Broker non-votes will be counted as present for purposes of determining the existence of a quorum.

(4)If your shares are held in “street name” through a bank, broker or other nominee, your brokerage firm may vote your shares under certain circumstances if you do not provide voting instructions. These circumstances include certain “routine” matters, such as the ratification of the appointment of our independent registered public accountants. Therefore, if you do not vote your proxy, your brokerage firm may either vote your shares on routine matters or leave your shares unvoted. When a brokerage firm votes its customers’ unvoted shares on routine matters without receiving voting instructions, these shares are counted for purposes of establishing a quorum to conduct business at the meeting and in determining the number of shares voted FOR or AGAINST the routine matter.

What happens if a nominee is unable to stand for re-election?

The Board may, by resolution, provide for a lesser number of directors or designate a substitute nominee. In the latter event, shares represented by proxies may be voted for a substitute nominee.

What happens if I sign and return my proxy card but do not provide voting instructions?

If you return a signed card but do not provide voting instructions, your shares will be voted FOR the nine named director nominees, FOR the ratification of the appointment of the independent registered public accountants, and FOR approval

82 2026 Proxy Statement

Questions and Answers About the Proxy Materials and Annual Meeting

of the compensation of the Company’s named executive officers. In addition, your proxy will be voted in the discretion of Mr. Stewart and/or Ms. Novoseletsky with respect to any other business that properly comes before the meeting.

If you mark your voting instructions on the proxy card, your shares will be voted as you instruct.

Where do I find the voting results of the meeting?

We will announce preliminary voting results at the meeting and will publish the final results in a Current Report on Form 8-K filed with the SEC within four business days after the meeting.

Is the proposed Merger with 365 conditioned on the results of the Annual Meeting?

As previously disclosed, on June 15, 2025, the Company entered into a Merger Agreement with 365. Pursuant to the terms and conditions set forth in the Merger Agreement, a wholly-owned subsidiary of 365 will merge with and into the Company, with the Company surviving the Merger as a wholly-owned indirect subsidiary of 365. The Merger Agreement has been unanimously adopted by the Board, and, at a special meeting of shareholders on September 4, 2025, the Company’s shareholders approved a proposal to approve and adopt the Merger Agreement, including the Merger.

Completion of the Merger is subject to the satisfaction of several conditions, including receipt of required clearance under the HSR Act.  The proposed Merger is not conditioned on the results of the Annual Meeting. Assuming receipt of required clearance pursuant to the HSR Act and timely satisfaction of the other then-remanding closing conditions, we currently expect the closing of the Merger to occur in the first half of calendar year 2026.

2026 Proxy Statement 83

Other Information About the Annual Meeting
Expenses of Solicitation
All costs of solicitation of proxies will be borne by the Company. In addition to solicitations by mail, our directors, officers and employees, without additional remuneration, may solicit proxies by telephone and personal interviews. Brokers, custodians and fiduciaries will be requested to forward proxy soliciting material to the owners of stock held in their names, and we will reimburse them for their related out-of-pocket expenses.

Householding

As permitted by the Exchange Act, only one copy of the Notice is being delivered to shareholders residing at the same address, unless such shareholders have notified us of their desire to receive multiple copies of the proxy statement or Annual Report. We will promptly deliver, upon oral or written request, a separate copy of the Annual Report or proxy statement, as applicable, to any shareholder residing at an address to which only one copy was mailed. Requests for additional copies should be directed to the Corporate Secretary at 101 Lindenwood Drive, Suite 120, Malvern, Pennsylvania 19355 or (800) 633-0340.

Shareholders residing at the same address and currently receiving only one copy of the Notice may contact the Corporate Secretary at 101 Lindenwood Drive, Suite 120, Malvern, Pennsylvania 19355 or (800) 633-0340, to request multiple copies in the future. Shareholders residing at the same address and currently receiving multiple copies may contact the Corporate Secretary to request that only a single copy of the Notice be mailed in the future.

84 2026 Proxy Statement

Other Information About the Annual Meeting

2027 Shareholder Proposals and Director Nominations

Pursuant to Rule 14a-8 of the Exchange Act, proposals of shareholders for possible consideration at the 2027 Annual Meeting of Shareholders (the “2027 Annual Meeting”) must be received by the Corporate Secretary of the Company before the close of business on June 12, 2026 to be included in the proxy statement for that meeting, if appropriate for consideration under applicable securities laws.

Our bylaws provide for the right of proxy access, which enables shareholders, under specified conditions, to include their nominees for election as directors in our proxy statement. Pursuant to our bylaws, a shareholder (or group of up to 20 shareholders) who has continuously owned at least 3% of our outstanding capital stock for at least three consecutive years may nominate up to 20% of the Board (but in any event at least two directors) and have such nominee(s) included in the our proxy statement, if the shareholder(s) and the nominee(s) satisfy the applicable requirements set forth in our bylaws. If a shareholder is seeking to have one or more nominees included in our 2026 proxy statement, the notice required by our bylaws must be received by the Secretary of the Company not later than June 12, 2026, and not earlier than May 13, 2026 unless our annual meeting date occurs more than 30 days before or 60 days after November 19, 2026. In that case, we must receive the nominations not earlier than the close of business on the 180th day prior to the date of the 2027 Annual Meeting and not later than the close of business on the later of: (i) the 90 days prior to the date of the 2026 Annual Meeting; or (ii) the 10 days following the day on which we first make a public announcement of the date of the 2027 Annual Meeting.

In addition, our bylaws provide that, in order to be properly brought before the 2027 Annual Meeting, a shareholder’s notice of a matter that the shareholder wishes to present (other than a matter brought pursuant to Rule 14a-8 promulgated under the Exchange Act), as well as any director nominations (other than the proxy access provisions described above), must be received by the Secretary of the Company not less than 60 nor more than 90 days before the first anniversary of the date of the 2026 Annual Meeting. As a result, any notice given by a shareholder pursuant to these provisions of our Bylaws (and not pursuant to Rule 14a-8 promulgated under the Exchange Act) must be received no earlier than August 21, 2026, and no later than the close of business on September 20, 2026, unless our annual meeting date occurs more than 30 days before or 60 days after November 19, 2026. In that case, we must receive proposals not earlier than the close of business on the 90th day prior to the date of the 2026 Annual Meeting and not later than the close of business on the later of: (i) the 60th day prior to the date of the 2027 Annual Meeting; or (ii) the 10th day following the day on which we first make a public announcement of the date of the 2027 Annual Meeting.

In addition to satisfying the foregoing requirements under our bylaws, to comply with the universal proxy rules under the Exchange Act, shareholders who intend to solicit proxies in support of director nominees other than the Company’s nominees must provide notice that sets forth the information required by Rule 14a-19 under the Exchange Act.

Notices discussed above and requests for copies of the relevant bylaw provisions regarding the requirements for making shareholder proposals and director nominations may be sent to our Corporate Secretary at our principal executive office as follows: Cantaloupe, Inc., 101 Lindenwood Drive, Suite 120, Malvern, Pennsylvania 19355, Attn: Corporate Secretary.

2026 Proxy Statement 85

Other Matters

The Board does not know of any other matters which may come before the meeting. If any other matters are properly presented to the meeting, the proxy holders intend to vote, or otherwise to act, in accordance with their judgment on such matters.

86 2026 Proxy Statement

Special Note Regarding Forward-Looking Statements

This proxy statement contains certain forward-looking statements within the meaning of Section 21E of the Securities Exchange Act of 1934, as amended. For this purpose, forward-looking statements are any statements contained herein that are not statements of historical fact and include, but are not limited to, those preceded by or that include the words “estimate,” “could,” “should,” “would,” “likely,” “may,” “will,” “plan,” “intend,” “believes,” “expects,” “anticipates,” “projected,” or similar expressions. Those statements are subject to known and unknown risks, uncertainties and other factors that could cause the actual results to differ materially from those contemplated by the statements. The forward-looking information is based on various factors and was derived using numerous assumptions. Important factors that could cause the Company’s actual results to differ materially from those projected include, for example: disruption to our business caused by the acquisition of us by 365; our ability to consummate the transaction with 365 within the contemplated timeframe, or at all, including risks and uncertainties related to securing the necessary regulatory approvals and the satisfaction of other closing conditions; the impact on our stock price, business, financial condition and results of operations if the proposed transaction with 365 is not consummated; costs, charges and expenses relating to the proposed transaction with 365; proceedings, including litigation that seeks to prevent the proposed transaction with 365 from being consummated within the contemplated timeframe, or at all; general economic, market or business conditions unrelated to our operating performance, including inflation, elevated interests rates, supply chain disruptions, financial institution disruptions, geopolitical conflicts, public health emergencies, and declines in consumer confidence and discretionary spending; our ability to compete with our competitors and increase market share;  failure to comply with the financial covenants in our debt facilities; our ability to maintain compliance with rules and regulations applicable to our business operations and industry; disruptions in other card payment processors, software and manufacturing partners upon whom we rely; whether our customers continue to utilize our transaction processing and related services, as our customer agreements are generally cancellable by the customer with thirty days’ notice; our ability to acquire and develop relevant technology offerings for current, new and potential customers and partners; risks and uncertainties associated with our expansion into and our operations in Europe, Mexico and other foreign markets, including general economic conditions, policy changes affecting international trade (including the imposition of new tariffs, or changes and adjustments to existing tariffs), political instability, inflation rates, recessions, sanctions, foreign currency exchange rates and controls, foreign investment and repatriation restrictions, legal and regulatory constraints, civil unrest, armed conflict, war, and other economic and political factors; our ability to satisfy our trade obligations included in accounts payable and accrued expenses; our ability to attract, develop and retain key personnel, or our loss of the services of our key executives; the incurrence by us of any unanticipated or unusual non-operating expenses, which may require us to divert our cash resources from achieving our business plan; our ability to predict or estimate our future quarterly or annual revenue and expenses given the developing and unpredictable market for our products; our ability to successfully integrate acquired companies into our current products and services structure; our ability to add new customers and retain key existing customers from whom a significant portion of our revenue is derived; the ability of a key customer to reduce or delay purchasing products from us; our ability to obtain widespread commercial acceptance of our products and service offerings; whether any patents issued to us will provide any competitive advantages or adequate protection for our products, or would be challenged, invalidated or circumvented by others;  the ability of our products and services to avoid disruptions to our systems or unauthorized hacking or credit card fraud; risks associated with cyber-attacks and data breaches; and our ability to maintain effective internal controls and to timely file periodic and current reports with the Securities and Exchange Commission (“SEC”). Actual results or business conditions may differ materially from those projected or suggested in forward-looking statements as a result of various factors including, but not limited to, those described above and in Part I, Item 1A, “Risk Factors” of our Annual Report on Form 10-K, filed with the SEC on

2026 Proxy Statement 87

September 8, 2025. We cannot assure you that we have identified all the factors that create uncertainties. Moreover, new risks emerge from time to time and it is not possible for our management to predict all risks, nor can we assess the impact of all risks on our business or the extent to which any risk, or combination of risks, may cause actual results to differ from those contained in any forward-looking statements. Readers should not place undue reliance on forward-looking statements. Any forward-looking statement made by us in this proxy statement speaks only as of the date of this proxy statement. Unless required by law, we undertake no obligation to publicly revise any forward-looking statement to reflect circumstances or events after the date of this proxy statement or to reflect the occurrence of unanticipated events.

88 2026 Proxy Statement

Appendix A - GAAP to Non-GAAP Reconciliation of Adjusted EBITDA

Below is a reconciliation of U.S. GAAP net (income) loss to Adjusted EBITDA for the fiscal years ended June 30, 2025, 2024, and 2023:

						Year ended June 30,
($ in thousands)						2025						2024						2023
Net income (loss)			$	64,533											$    11,993						$    633
Less: interest income			(1,561)												(1,969)						(2,515)
Plus: interest expense			2,769												2,934						2,326
Plus: income tax provision			(42,352)												985						181
Plus: depreciation expense included in cost of sales for rentals			1,923												1,634						1,189
Plus: depreciation and amortization expense in operating expenses			15,877												10,570						7,618
EBITDA			41,189												26,147						9,432
Plus: stock-based compensation(a)			4,008												5,109						4,737
Plus: investigation, proxy solicitation and restatement expenses, net of insurance recoveries(b)			—												(1,522)						(362)
Plus: integration, acquisition, due diligence, and license application expenses (c)			1,018												1,197						3,141
Plus: auditor transition costs			525												—						—
Plus: severance expenses(d)			—												53						273
Plus: remediation expenses(e)			—												2,976						573
Adjustments to EBITDA			5,551												7,813						8,362
Adjusted EBITDA			$ 46,740												$     33,960						$     17,794

(a)We have excluded stock-based compensation, as it does not reflect our cash-based operations.

(b) In fiscal year 2019, the Audit Committee, with the assistance of independent legal and forensic accounting advisors, conducted an internal investigation of then-current and prior period matters relating to certain of the Company’s contractual arrangements, including the accounting treatment, financial reporting and internal controls related to such arrangements (the “2019 Investigation”). We have excluded the costs and corresponding reimbursements related to the 2019 Investigation, because we believe that they represent charges that are not related to our core operations. During the year ended June 30, 2024, we received $1.5 million in insurance reimbursement for legal fees and expenses incurred in connection with the 2019 Investigation. Accordingly, Adjusted EBITDA contains a negative adjustment.

(c)We have excluded expenses incurred in connection with business acquisitions as it does not represent recurring costs or charges related to our core operations.

(d)Consists of expenses incurred in connection with non-recurring severance charges related to work force reduction.

(e)Consists of expenses incurred in connection with fully remediating previously identified material weaknesses in our internal control over financial reporting.

2026 Proxy Statement 89