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Upland Software (Nasdaq: UPLD) hires Jennifer Simon as new Chief Financial Officer

Filing Impact
(Moderate)
Filing Sentiment
(Neutral)
Form Type
8-K

Rhea-AI Filing Summary

Upland Software, Inc. appointed Jennifer Simon as Chief Financial Officer, effective August 17, 2026, making her the company’s principal financial and accounting officer. She previously held senior finance roles at NextGen Healthcare, Quest Software, and Community Impact Newspaper, and is a Texas Certified Public Accountant with advanced accounting degrees from the University of Texas at Austin.

Under her executive employment agreement, Simon will receive an annual base salary of $350,000, eligibility for an annual bonus of up to 75% of base salary, a grant of 30,000 restricted stock units vesting in 12 equal installments over three years, and performance-based RSUs with 6,666 units at target and up to 25,000 units at maximum. If terminated without cause or if she resigns for good reason, she is eligible for 12 months of base-salary continuation and reimbursement of the employer portion of COBRA premiums for up to 12 months, subject to ongoing compliance with her agreement. Simon succeeds founding executive Mike Hill, who will retire from the CFO role.

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Item 5.02 Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers Governance
Key personnel changes including departures, elections, or appointments of directors and executive officers.
Item 7.01 Regulation FD Disclosure Disclosure
Material non-public information disclosed under Regulation Fair Disclosure, often investor presentations or guidance.
Item 9.01 Financial Statements and Exhibits Exhibits
Financial statements, pro forma financial information, and exhibit attachments filed with this report.
CFO base salary $350,000 Annual base salary for Jennifer Simon starting on the Effective Date as CFO
Target bonus opportunity 75% of base salary Maximum annual bonus percentage for Jennifer Simon based on performance objectives
Time-based RSUs 30,000 units Restricted stock units granted to Jennifer Simon, vesting in 12 equal installments over three years
Target PRSUs 6,666 units Performance-Based RSUs eligible to vest at target performance for the new CFO
Maximum PRSUs 25,000 units Performance-Based RSUs eligible to vest at maximum performance for the new CFO
Severance term 12 months Base-salary continuation period after qualifying termination without cause or for good reason
COBRA reimbursement period up to 12 months Employer portion of COBRA premiums reimbursable after qualifying termination, subject to earlier cessation
Cost savings at prior employer $120 million Cost savings Jennifer Simon drove at Quest Software, as described in her background
restricted stock units financial
"a grant of 30,000 restricted stock units, which will vest in 12 equal installments"
Restricted stock units are a type of company reward where employees are promised shares of stock, but they only fully own these shares after meeting certain conditions, like staying with the company for a set time. They matter because they can become valuable assets and are often used to motivate employees to help the company succeed.
Performance-Based Restricted Stock Units financial
"a grant of Performance-Based Restricted Stock Units (“PRSUs”), which will vest based on performance goals"
Performance-based restricted stock units are a type of employee equity award that converts into company shares only if predefined financial or operational targets are met over a set period. Think of it like a bonus check that becomes stock only when specific goals are hit; it ties pay to results, aligning managers’ incentives with shareholders. Investors care because these awards affect future share count, executive incentives, and signal how management’s success will be measured and rewarded.
COBRA premiums financial
"reimbursement of the employer portion of COBRA premiums for up to twelve months"
Regulation FD regulatory
"Item 7.01. Regulation FD Disclosure."
Regulation FD is a rule that prevents company insiders, like executives, from sharing important information with some people before others get it. It matters because it helps ensure all investors have equal access to key news, making the stock market fairer and reducing chances of insider trading.
forward-looking statements regulatory
"Certain statements in this press release constitute forward-looking statements"
Forward-looking statements are predictions or plans that companies share about what they expect to happen in the future, like estimating sales or profits. They matter because they help investors understand a company's outlook, but since they are based on guesses and assumptions, they can sometimes be wrong.

AI-generated analysis. How Rhea-AI works. Not financial advice.

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FAQ

What executive leadership change did Upland Software (UPLD) announce?
Upland Software appointed Jennifer Simon as Chief Financial Officer, effective August 17, 2026. She becomes the company’s principal financial and accounting officer, succeeding founding executive Mike Hill as Upland continues its focus on AI-driven enterprise intelligence.

What is the compensation package for Upland Software (UPLD)’s new CFO?
Jennifer Simon will receive a $350,000 annual base salary, an annual bonus of up to 75% of base salary, 30,000 RSUs vesting over three years, and performance-based RSUs with 6,666 units at target and up to 25,000 units at maximum performance.

What severance protections does Upland Software (UPLD) provide to its new CFO?
If Upland terminates Jennifer Simon without cause or she resigns for good reason, she is eligible for 12 months of base-salary continuation and reimbursement of the employer portion of COBRA premiums for up to 12 months, conditioned on compliance with her agreement.

What prior experience does Jennifer Simon bring to Upland Software (UPLD)?
Jennifer Simon brings over 20 years of finance leadership, including Senior Vice President Finance at NextGen Healthcare and key roles at Quest Software, where she drove $120 million in cost savings, built ARR and SaaS metrics reporting, and led M&A diligence and a debt restructuring.

How do equity incentives for Upland Software (UPLD)’s CFO appointment work?
The package includes 30,000 time-based RSUs vesting in 12 equal installments over three years and performance-based RSUs that vest based on board-approved goals, with 6,666 units at target and up to 25,000 units at maximum, all subject to continued service.

Who will Jennifer Simon report to at Upland Software (UPLD)?
As Chief Financial Officer, Jennifer Simon will report to President and Chief Executive Officer Sean Nathaniel. She will oversee financial planning and analysis, accounting, treasury, tax, and investor relations as Upland advances its AI-focused strategic priorities.
0001505155false00015051552026-07-172026-07-170001505155upld:CommonStockParValue00001PerShareMember2026-07-172026-07-170001505155upld:PreferredStockPurchaseRightsMember2026-07-172026-07-17

UNITED STATES
SECURITIES AND EXCHANGE COMMISSION
Washington, DC 20549
FORM 8-K
CURRENT REPORT
Pursuant to Section 13 or 15(d) of
The Securities Exchange Act of 1934
July 17, 2026
Date of Report (Date of earliest event reported)
UPLAND SOFTWARE, INC.
(Exact name of registrant as specified in its charter)
Delaware
001-36720
27-2992077
(State or other jurisdiction of incorporation)
(Commission File Number)
(IRS Employer Identification No.)
900 S. Capital of Texas Highway, Las Cimas IV, Suite 300
Austin, Texas 78746
(Address of principal executive offices, including zip code)
(512) 960-1010
(Registrant’s telephone number, including area code)
Check the appropriate box below if the Form 8-K filing is intended to simultaneously satisfy the filing obligation of the registrant under any of the following provisions (see General Instruction A.2. below):
☐ Written communications pursuant to Rule 425 under the Securities Act (17 CFR 230.425)
☐ Soliciting material pursuant to Rule 14a-12 under the Exchange Act (17 CFR 240.14a-12)
☐ Pre-commencement communications pursuant to Rule 14d-2(b) under the Exchange Act (17 CFR 240.14d-2(b))
☐ Pre-commencement communications pursuant to Rule 13e-4(c) under the Exchange Act (17 CFR 240.13e-4(c))
Securities registered pursuant to Section 12(b) of the Act:
Title of each class
Trading Symbol
Name of each exchange on which registered
Common Stock, par value $0.0001 per share
UPLD
The Nasdaq Global Market
Preferred Stock Purchase Rights
-
The Nasdaq Global Market
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).
Emerging growth company    ☐
If an emerging growth company, indicate by check mark if the registrant has elected not to use the extended transition period for complying with any new or revised financial accounting standards provided pursuant to Section 13(a) of the Exchange Act.                                              ☐


Item 5.02 Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers.
On July 17, 2026, the board of directors (the “Board”) of Upland Software, Inc. (the “Company”) appointed Jennifer Simon to serve as Chief Financial Officer of the Company, effective as of August 17, 2026 (the “Effective Date”). In this capacity, Ms. Simon will be the Company’s principal financial and accounting officer.
Ms. Simon, age 51, has served as Senior Vice President Finance of NextGen Healthcare since January 2026. Prior to becoming Senior Vice President Finance of NextGen Healthcare, Ms. Simon served in various finance roles at Quest Software from July 2022 to October 2025, most recently serving as Vice President of Finance, FP&A of Quest Software from June 2025 to October 2025, as well as interim Chief Financial Officer from March 2025 to June 2025. Prior to joining Quest Software, Ms. Simon served as Chief Financial Officer of Community Impact Newspaper from February 2016 to July 2022. She is a Certified Public Accountant in the state of Texas and holds both a Masters in Professional Accounting and a Bachelor of Business Administration from the University of Texas at Austin.
In connection with Ms. Simon’s appointment as Chief Financial Officer, on July 17, 2026, the Company entered an executive employment agreement with Ms. Simon (the “Employment Agreement”). The Employment Agreement contains compensation terms to begin on the Effective Date as follows: (i) an annual base salary of $350,000, (ii) eligibility for an annual bonus of up to 75% of base salary, upon achievement of performance objectives determined by the Board, (iii) a grant of 30,000 restricted stock units, which will vest in 12 equal installments over three years, subject to Ms. Simon’s continued service, and (iv) a grant of Performance-Based Restricted Stock Units (“PRSUs”), which will vest based on the achievement of performance goals established by the Board or the Compensation Committee of the Board, subject to Ms. Simon’s continued service, with 6,666 PRSUs eligible to vest at target performance and up to 25,000 PRSUs eligible to vest at maximum performance.
If Ms. Simon’s employment is terminated by the Company for cause or if she resigns without good reason, she will be entitled to (i) her accrued but unpaid base salary, (ii) accrued but unused vacation, (iii) unreimbursed business expenses and (iv) any other vested benefits in accordance with applicable plans. She will not be entitled to any additional compensation or benefits. If Ms. Simon’s employment is terminated by the Company without cause or if she resigns for good reason, she will be entitled to (i) continued payment of her base salary for twelve months following such termination and (ii) reimbursement of the employer portion of COBRA premiums for up to twelve months, subject to earlier cessation upon specified events. Any such severance payments and benefits are subject to Ms. Simon’s continued compliance with the Employment Agreement.
No family relationships exist between Ms. Simon and any of the Company’s directors or executive officers or any person nominated or chosen by the Company to become a director or executive officer. Other than with respect to the compensation matters, as described above, there are no arrangements or understandings between Ms. Simon and any other person pursuant to which Ms. Simon was selected as Chief Financial Officer of the Company, nor are there any transactions to which the Company is or was a participant and in which Ms. Simon has or had a direct or indirect material interest subject to disclosure under Item 404(a) of Regulation S-K.

Item 7.01. Regulation FD Disclosure.
On July 21, 2026, the Company issued a press release announcing the appointment of Ms. Simon as Chief Financial Officer. The text of the press release is attached as Exhibit 99.1 to this Form 8-K. The information in Item 7.01 of this Current Report on Form 8-K, including Exhibit 99.1, is being furnished and shall not be deemed “filed” for the purposes of Section 18 of the Securities Exchange Act of 1934, as amended (the “Exchange Act”), or otherwise subject to the liabilities of that section, nor shall it be deemed incorporated by


reference in any filing under the Securities Act of 1933, as amended, or the Exchange Act, except as expressly set forth by specific reference in such a filing.

Item 9.01      Financial Statements and Exhibits.
(d) Exhibits.
Exhibit No.
 
Description
99.1
Press Release of Upland Software, Inc. dated July 21, 2026
104
The cover page from this Current Report on Form 8-K, formatted as Inline XBRL


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 thereunto duly authorized.
UPLAND SOFTWARE, INC.
By:
/s/ Michael D. Hill
Michael D. Hill
Chief Financial Officer
Date: July 21, 2026




Exhibit 99.1
Upland Software Appoints Jennifer Simon as Chief Financial Officer
Veteran finance executive with two decades of software and private equity-backed leadership experience to join Upland effective August 17

AUSTIN, Texas — (BUSINESS WIRE) — Upland Software, Inc. (Nasdaq: UPLD) (the "Company" or "Upland"), a provider of enterprise intelligence that turns knowledge, content, and data into actionable AI-powered outcomes, today announced the appointment of Jennifer Simon, CPA, as Chief Financial Officer, effective August 17, 2026. Jennifer will lead Upland's global finance organization, reporting to President and Chief Executive Officer Sean Nathaniel.
Jennifer brings more than 20 years of finance leadership across software, technology, and private equity-backed environments. She joins Upland from NextGen Healthcare, where she served as Senior Vice President of Finance. Immediately prior, she spent more than three years at Quest Software, a $1 billion private equity-backed global software company much like Upland, rising from Vice President of Finance to Interim CFO. There she drove $120 million in cost savings, built the company's ARR and SaaS metrics reporting, led diligence across multiple M&A processes, and executed a debt restructuring. She also previously served as Chief Financial Officer of Community Impact Newspaper, where she helped scale the company from 20 to 41 markets. She is a Certified Public Accountant with a Master's in Professional Accounting from the University of Texas at Austin.
In the role, Jennifer will oversee financial planning and analysis, accounting, treasury, tax, and investor relations, working closely with Upland's leadership team to strengthen financial and operating discipline, support effective capital allocation and investment decisions, and advance the Company's strategic priorities. Jennifer’s appointment comes as Upland sharpens its strategic focus to its core intelligence domains of knowledge, content, and data, prioritizing disciplined capital allocation as the Company invests in AI-driven product innovation and strengthens its balance sheet.
"Since becoming CEO, my focus has been on sharpening our strategy, simplifying how we operate, and strengthening our leadership team," said Sean Nathaniel, President and Chief Executive Officer of Upland Software. "Jennifer's appointment marks an important milestone in that work. She brings significant software transformation experience, financial discipline, and a strong operating perspective. I look forward to partnering with her as we build a more focused and agile organization, thoughtfully apply AI across our products and operations, and strengthen business performance."
"I am excited to join Upland at an important point in its transformation," said Jennifer Simon. "Upland has strong customer relationships, a portfolio of mission-critical products, and meaningful opportunities ahead. I look forward to partnering with Sean and the leadership team to strengthen execution and create long-term value for our customers and shareholders."
Jennifer succeeds Mike Hill, one of Upland's founding team members, who will retire from his role as Chief Financial Officer following an illustrious career with the Company. Prior to his departure, Mike has partnered closely with CEO Sean Nathaniel to support his transition into the CEO role.

About Upland Software
Upland Software (Nasdaq: UPLD) provides an intelligence layer that unifies and contextualizes enterprise knowledge, content, and data, turning isolated information into actionable outcomes for every human and agent. More than 1,100 enterprise customers rely on Upland's deep domain expertise to drive measurable, value-add outcomes, unlocking the full potential of AI as their organizations evolve. For more information, visit www.uplandsoftware.com.




Forward-Looking Statements
Certain statements in this press release constitute forward-looking statements under the Private Securities Litigation Reform Act of 1995. These statements involve risks and uncertainties that may cause actual results to differ materially from those anticipated. For additional information, please refer to Upland's filings with the Securities and Exchange Commission.

Contacts:
Investor Relations Contact:
Michael D. Hill
512-960-1031
investor-relations@uplandsoftware.com

Media Contact:
Lloyd Berry
512-960-1010
media@uplandsoftware.com
Source: Upland Software, Inc.

Source: View Original Filing on SEC EDGAR

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