Pineapple Financial names Usman Maher CFO
PTIV trading is anticipated on or about October 26, while the proposed corporate renaming and strategic transactions remain subject to approval and review.
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Rhea-AI Filing Summary
Pineapple Financial Inc. appointed Usman Maher Chief Financial Officer and Chief Strategy Officer effective October 15, 2026; Syed Sarfraz Habib became Chief Accounting Officer and Controller. Habib remains principal financial officer and principal accounting officer through the filing of the fiscal 2026 Form 10-K; afterward, Maher assumes the principal financial officer designation and Habib remains principal accounting officer. Maher’s agreement provides a $250,000 annual base salary accruing from October 1, 2026, and a target annual bonus of 100% of base salary, with payouts from 50% at threshold to 150% at maximum. Equity awards are subject to Board and Compensation Committee approval.
The company announced the Pentiv operating brand and launched an intelligence platform for mortgage agents and brokerages; its Recruitment Agent and Alternative Mortgage Renewal Agent already operate in Pineapple+. A special committee of independent directors is reviewing a proposed repositioning that includes delineating the technology platform and digital-asset treasury operations from mortgage brokerage and a potential subsequent spin-off. The non-binding proposal remains subject to review, definitive agreements and approvals. Trading under PTIV is anticipated on or about October 26, 2026; the corporate renaming to Pentiv Inc. requires shareholder approval.
Filing Explained
To show progress from internal proof toward third-party commercialization, the company says it intends to report adoption and outcomes inside Pineapple, additional deployments, external pilots and customer agreements, and recurring platform revenue in coming quarters.
8-K Event Classification
Key Figures
Key Terms
Management Incentive Plan financial
non-binding term sheet financial
asset-light operating model technical
system of record technical
recurring platform revenue financial
FAQ
AI-generated questions and answers. How Rhea-AI works. Not financial advice.
What are Pineapple Financial (PAPL) CFO Usman Maher's compensation terms?
What is Pineapple Financial (PAPL) proposing with its Pentiv repositioning?
Who is on the Pineapple Financial (PAPL) special committee?
When will Pineapple Financial (PAPL) change its ticker to PTIV?
What does Pineapple Financial's (PAPL) Pentiv platform offer mortgage brokerages?
AI-generated analysis. How Rhea-AI works. Not financial advice.
UNITED STATES
SECURITIES AND EXCHANGE COMMISSION
Washington, D.C. 20549
FORM
CURRENT REPORT
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Indicate by check mark whether the registrant is an emerging growth company as defined in Rule 405 of the Securities Act of 1933 (§230.405 of this chapter) or Rule 12b-2 of the Securities Exchange Act of 1934 (§ 240.12b-2 of this chapter).
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Item 5.02 Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers.
Chief Financial Officer Transition
On October 9, 2026, the Board of Directors (the “Board”) of Pineapple Financial Inc. (the “Company”) approved a transition of the Company’s finance leadership. Effective October 15, 2026, Usman Maher was appointed Chief Financial Officer and Chief Strategy Officer of the Company.
Syed Sarfraz Habib, who has served as the Company’s Chief Financial Officer, was appointed Chief Accounting Officer and Controller of the Company. Mr. Habib’s transition is not the result of any disagreement with the Company on any matter relating to the Company’s operations, policies or practices.
The appointment reflects the Company’s focus on strengthening its finance and strategy functions as it scales the Pentiv platform, including institutional-grade financial planning and analysis, capital-markets execution, and the reporting infrastructure to support the Company’s commercial milestones.
Mr. Maher, age 40, brings nearly two decades of experience across hedge fund investing, private equity, special situations credit, and high-growth financial technology. From 2022 to 2026, he served as Senior Director, Strategic Finance at SoFi Technologies, Inc., where he built the finance function for SoFi’s member platform. From 2020 to 2021, he served as a consultant on transactions and diligence matters for investment management firms. From 2016 to 2020, he served in roles of increasing seniority, most recently Vice President, at Lone Star Funds, focused on private equity and special situations investments. Mr. Maher has been a CFA charterholder since 2011 and holds an M.B.A. from the University of Chicago Booth School of Business.
Employment Agreement
In connection with Mr. Maher’s appointment, the Company and Mr. Maher entered into an Executive Employment Agreement, dated as of October 9, 2026 (the “Employment Agreement”), under which Mr. Maher will receive an annual base salary of $250,000, accruing from October 1, 2026. Mr. Maher will participate in the Company’s Management Incentive Plan, with a target annual bonus of 100% of base salary and a payout range of 50% of base salary at threshold to 150% at maximum. Mr. Maher will also be granted equity awards subject to Board and Compensation Committee approval and to the terms of the Company’s 2022 Omnibus Equity Incentive Plan and 2021 Stock Option Plan. The foregoing description of the Employment Agreement does not purport to be complete and is qualified in its entirety by reference to the full text of the Employment Agreement, which is filed as Exhibit 10.1 to this Current Report and incorporated herein by reference.
Principal Financial Officer and Principal Accounting Officer Designations
Mr. Habib shall continue to serve as the Company’s “principal financial officer” and “principal accounting officer” for all purposes of the U.S. Securities Exchange Act of 1934 and the rules thereunder through the filing of the Company’s Annual Report on Form 10-K for the fiscal year ended August 31, 2026 (the “Form 10-K”) and the certifications and other filings related thereto. Upon the filing of the Form 10-K, Mr. Maher shall, without further action of the Board, assume the designation of “Principal Financial Officer”, and Mr. Habib shall continue as “Principal Accounting Officer” of the Company.
Item 7.01 Regulation FD Disclosure.
On October 15, 2026, the Company issued a press release announcing the matters described in this Current Report and made available an investor presentation. Copies of the press release and the investor presentation are furnished as Exhibit 99.1 and Exhibit 99.2, respectively, to this Current Report. The information in this Item 7.01, including Exhibits 99.1 and 99.2, is being furnished and shall not be deemed “filed” for purposes of Section 18 of the Securities Exchange Act of 1934, as amended, or otherwise subject to the liabilities of that Section, and shall not be deemed incorporated by reference into any filing under the Securities Act of 1933, as amended, except as expressly set forth by specific reference in such filing.
Item 8.01 Other Events
Formation of Special Committee
On October 9, 2026, the Board of the Company formed a special committee of the Board (the “Special Committee”) to oversee management’s evaluation of a proposed multi-phase strategic repositioning of the Company under the “Pentiv” brand and related transactions (together, the “Proposed Transactions”). The repositioning encompasses a proposed corporate renaming, the delineation of the Company’s technology platform and digital-asset treasury operations from its mortgage brokerage operations, and continued investment in the development and commercialization of the Pentiv platform, including deployment of its AI-enabled workflows within the Company’s brokerage network, potential licensing of the platform to third-party brokerages, and potential longer-term data-product offerings. The Proposed Transactions also contemplate a potential subsequent spin-off of the Company’s mortgage brokerage business. The related ticker symbol change is described separately below.
The Proposed Transactions are described in a non-binding term sheet dated September 16, 2026. The Special Committee was formed because of the related-party nature of certain elements of the Proposed Transactions. Management’s proposal is intended to accelerate the Company’s strategy of developing and commercializing technology through its operating mortgage brokerage. The proposed structure could position Pentiv to serve a broader market while retaining the brokerage as an anchor customer and a source of operating data and product feedback. The brokerage, in turn, could benefit from dedicated ownership and continued access to the platform under contemplated long-term commercial and technology agreements. The proposal’s objective is to strengthen both businesses and enhance long-term shareholder value. The Proposed Transactions remain subject to the Special Committee’s review, negotiation and execution of definitive agreements, and applicable approvals. The term sheet does not predetermine the outcome of that review, and there can be no assurance that any transaction will be pursued or completed, or as to its terms, timing or anticipated benefits.
The Special Committee consists solely of independent directors: Anthony Georgiades (Chair), Drew Green, Paul Baron and Tasis Giannoukakis. The Board has authorized the Special Committee to, among other things, evaluate, review, direct, supervise and, where it determines appropriate, conduct negotiations regarding the Proposed Transactions or any potential alternative transaction. The Special Committee may also retain independent legal, financial and other advisors at the Company’s expense, and commission any valuation or fairness opinion it considers appropriate.
Ticker Symbol Change
On October 15, 2026, the Company announced that as part of its rebranding initiatives, its stock ticker symbol on the New York Stock Exchange (the “NYSE”) will change from “PAPL” to “PTIV”. Trading under the new stock ticker symbol is anticipated to begin on or about October 26, 2026. The Company’s common shares will continue to be listed on the NYSE, and the Company’s CUSIP will remain unchanged. The renaming of the Company to “Pentiv Inc.” remains subject to shareholder approval at a future meeting of shareholders; unless and until such approval is obtained and the renaming becomes effective, the Company’s filings with the Securities and Exchange Commission will continue to be made under the name Pineapple Financial Inc.
Forward-Looking Statements
This Current Report on Form 8-K contains forward-looking statements, including statements regarding the anticipated timing of the ticker symbol change, the proposed corporate renaming, and the evaluation of the Proposed Transactions. These statements are subject to risks and uncertainties, including those described in the Company’s filings with the Securities and Exchange Commission, and actual results may differ materially. The Company undertakes no obligation to update forward-looking statements except as required by law.
Item 9.01 Financial Statements and Exhibits.
(d) Exhibits.
| 10.1 | Executive Employment Agreement, dated as of October 9, 2026, between the Company and Usman Maher |
| 99.1 | Press release, dated October 15, 2026 |
| 99.2 | Investor presentation, dated October 2026 |
| 104 | Cover Page Interactive Data File (embedded within the Inline XBRL document) |
SIGNATURE
Pursuant to the requirements of the Securities Exchange Act of 1934, the registrant has duly caused this report to be signed on its behalf by the undersigned hereunto duly authorized.
Date: October 15, 2026
| PINEAPPLE FINANCIAL INC. | ||
| By: | /s/ Shubha Dasgupta | |
| Shubha Dasgupta | ||
| Chief Executive Officer | ||
Exhibit 99.1
Pentiv Launches Intelligence Platform for Mortgage Agents and Brokerages
Pineapple Financial evolves into Pentiv, combining its established mortgage operating platform with a new asset-light intelligence model; Usman Maher appointed Chief Financial Officer and Chief Strategy Officer
Toronto, Ontario—October 15, 2026—Pentiv (NYSE American: PAPL), the new operating brand of Pineapple Financial Inc., today announced the launch of its intelligence platform for mortgage agents and brokerages, marking the next phase of the company’s evolution. The platform builds on technology, permissioned data, and workflows developed within Pineapple Financial’s operating network and is designed for broader commercialization across independent brokerages and mortgage networks. The company also announced the appointment of Usman Maher as Chief Financial Officer and Chief Strategy Officer. The company’s common shares will continue to trade under the ticker “PAPL” until the ticker change to “PTIV” becomes effective on NYSE American, which is anticipated to occur on or about October 26, 2026. The corporate renaming to “Pentiv Inc.” remains subject to shareholder approval at the company’s upcoming meeting of shareholders.
Pentiv launches with an asset-light operating model and a growing base of recurring platform revenue. Rather than replace the origination systems brokerages already use, Pentiv is designed to sit above existing infrastructure, unify data and workflows, and apply intelligence to the operating functions that drive brokerage growth. That architecture gives the company a path to scale software and intelligence products beyond the economics of a single brokerage network.
Pentiv’s core operating strategy centers on the commercialization and expansion of its mortgage-intelligence platform. Pineapple Financial serves as the operating foundation, customer zero, and proof environment where products can be developed, tested, and measured in real brokerage workflows before broader deployment. The company’s digital asset treasury and broader treasury strategy provide supporting balance-sheet and capital infrastructure for its longer-term thesis that AI and on-chain finance will increasingly converge, giving Pentiv a vested role in the blockchain network that supports that future.
Mortgage technology has historically focused on automating the loan file, from origination and underwriting to document processing and funding. Pentiv focuses on a different layer: the brokerage itself. Its platform combines brokerage data and workflows in a unified system of record, beginning with applications for recruiting and alternative-mortgage renewals. Pentiv’s roadmap extends that intelligence across onboarding, retention, borrower engagement, and other functions throughout the brokerage lifecycle.
Usman Maher has joined Pentiv as CFO and Chief Strategy Officer. Maher brings more than a decade of experience across private equity, special situations credit, and high-growth fintech. Before joining Pentiv, he served as Senior Director of Strategic Finance at SoFi, where he built the finance function for the company’s member platform and helped scale it into a meaningful contributor to P&L. At Pentiv, Maher will lead financial operations and strategic direction, including platform strategy, capital allocation, reporting, governance, and execution against the company’s commercial milestones.
“At a time when many AI solutions in mortgage appear designed to automate brokerage professionals out of the process, we believe human judgment, trust, and relationships remain essential,” said Usman Maher, Chief Financial Officer and Chief Strategy Officer of Pentiv. “Pentiv is launching a solution that helps brokerages harness AI to compete with large technology platforms while strengthening the professionals at the center of the mortgage process. We will prove the economics inside Pineapple, extend the platform to external brokerages, and scale adoption to build a durable intelligence company and long-term shareholder value.”
Pineapple Financial provides Pentiv with integrated systems, mortgage data, active brokerage workflows, and direct feedback from mortgage professionals using its tools in their day-to-day work. Pentiv’s initial applications, a Recruitment Agent and an Alternative Mortgage Renewal Agent, already operate within Pineapple+, Pineapple Financial’s integrated application environment. The Recruitment Agent is designed to help brokerage leaders identify promising mortgage professionals, prioritize outreach, and manage recruiting workflows. The Alternative Mortgage Renewal Agent is designed to surface at-risk or upcoming alternative-mortgage renewals, suggest outreach, manage documentation, and help mortgage professionals retain more customers and mortgage balances.
“We have spent years building technology around how mortgage professionals actually operate, where friction exists, how brokerages recruit and retain talent, and how agents stay close to borrowers,” said Shubha Dasgupta, CEO of Pentiv and Pineapple Financial. “Pentiv gives us the opportunity to take what we have built and learned inside Pineapple and extend it to the broader industry. Pineapple will remain the environment where we can test, validate, and improve the platform in real workflows, while Pentiv gives us the vehicle to scale that intelligence far beyond our own network. That is what makes this next phase so exciting.”
The opportunity extends materially beyond Pineapple. Mortgage distribution in Canada operates through a large and fragmented network of independent brokerages and mortgage professionals that often rely on multiple disconnected systems, while broker penetration among recent homebuyers continues to grow. Mortgage Professionals Canada’s 2026 consumer research found that 38% of recent homebuyers obtained their mortgage through a broker, up six percentage points from 2024. Among recent first-time buyers, the share reached 48%, an increase of 10 percentage points. In Ontario alone, licensed mortgage brokerages originated more than 270,000 mortgages representing over C$158 billion in volume in 2024, across a channel that includes more than 1,100 independent brokerages. Together, these figures underscore the scale and growing relevance of the broker channel.
Over the coming quarters, Pentiv intends to report against defined commercial and operating proof points, including adoption and measurable outcomes from its recruiting and renewal applications inside Pineapple, additional product deployments, external brokerage pilots and customer agreements, and growth in recurring platform revenue. These milestones are intended to give investors and customers a clear view of the company’s progress from internal proof to third-party commercialization. Pentiv expects to provide additional detail regarding its platform strategy, operating KPIs, and capital allocation framework through future earnings updates and investor communications.
For more information, visit PentivHQ.com.
About Pentiv
Pentiv, the operating brand of Pineapple Financial Inc., is the intelligence platform for the mortgage brokerage industry. It unifies the data, workflows, and applied intelligence behind recruiting, onboarding, retention, borrower engagement, and renewals. Operating from a unified system of record, its solutions reduce administrative work, surface actionable opportunities, and help brokerages scale efficiently while enabling agents to serve more clients, close more business, and grow their books. Pentiv is the operating brand of Pineapple Financial Inc.; the company’s securities filings continue to be made under the legal name Pineapple Financial Inc. pending shareholder approval of the corporate renaming. For more information, visit PentivHQ.com.
Media Contact
Avenue Z
pentiv@avenuez.com
Safe Harbor Forward-Looking Statements
Certain statements in this announcement are forward-looking statements. These forward-looking statements involve known and unknown risks and uncertainties. They are based on the Company’s current expectations and projections about future events that the Company believes may affect its financial condition, results of operations, business strategy and economic needs. These statements are generally identified by words such as “may,” “will,” “could,” “should,” “would,” “intends,” “expects,” “plans,” “anticipates,” “believes,” “estimates,” “seeks,” “designed,” “roadmap,” “potential,” “opportunity,” and similar expressions, although not all forward-looking statements contain these words. Forward-looking statements are not guarantees of future performance and are based on current expectations and assumptions that are subject to risks and uncertainties. Actual results and events could differ materially from those expressed or implied by these statements and other risks and uncertainties described in the Company’s filings with the Securities and Exchange Commission and other applicable securities regulators. Readers are cautioned not to place undue reliance on these forward-looking statements, which speak only as of the date of this press release. Pentiv undertakes no obligation to update or revise any forward-looking statements, except as required by law.
Exhibit 99.2
Filing Exhibits & Attachments
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