📄 What This Document Is 📜

This filing is a Proxy Statement (DEF 14A), which is a comprehensive guide sent to Upland Software's stockholders before an Annual Meeting. Its primary purpose is to explain all the proposals that stockholders will vote on, including changes to corporate structure, executive compensation, and the company's governance.

👉 What to expect: The document details the logistics for the 2026 Annual Meeting on June 3, 2026, and outlines six specific items requiring a vote.

🏢 Upland Software Overview 💻

While this document focuses heavily on governance and votes, we can learn that Upland Software is a technology company that provides software and services. The company has a history of expanding its operations and leadership, with key personnel having backgrounds in various sectors, including finance, technology, and consulting.

👉 How to fund the operation: The company relies on its board and committee structure to manage risks and guide its financial and operational reporting.

📅 Annual Meeting & Voting Logistics 🗳️

The annual meeting is the central event for the stockholders, determining the fate of several corporate proposals. Stockholders have multiple ways to cast their votes, and advance voting is strongly encouraged.

• Meeting Details: The Annual Meeting is scheduled for June 3, 2026, at 11:00 a.m. Central Daylight Time. The physical address is 900 S. Capital of Texas Highway, Las Cimas IV, Suite 300, Austin, Texas 78746.
• Record Date: The crucial date for determining who is eligible to vote is the Record Date, which was April 13, 2026.
• Voting Tip: Stockholders do not need to attend the meeting to cast their vote; they can submit a proxy by the Internet, phone, or mail.

🏛️ Corporate Governance Structure 🌐

Corporate governance defines how the company is managed and regulated. Upland's Board of Directors is divided into three classes, and the company has established multiple committees to handle specific, complex areas of oversight.

• The Board: The current Board has six members, four of whom are considered "independent directors" (meaning they are not employees or closely related parties to the company).
• Leadership: John T. (Jack) McDonald serves as the Chairman of the Board, and David D. May serves as the Lead Independent Director.
• Committees: The board maintains three standing committees—the Audit, Compensation, and Nominating and Governance Committees—all of which are staffed by independent directors. This separation of duties is standard practice to ensure objective oversight.

💼 Founder Transition and Leadership Changes 🧑‍💼

A major point of focus is the leadership transition, as the founder is scheduled to step down from key roles.

• CEO/President Transition: John T. (Jack) McDonald, who founded Upland in 2010, is scheduled to retire from his roles as Chief Executive Officer and President on April 30, 2026.
• Roles: Until that date, Mr. McDonald’s roles as Chair, CEO, and President remain combined. The Board believes that he is best suited for this combined role because he is the most familiar with the company’s business and history.
• Commitment: Despite the transition, Mr. McDonald will continue to serve as the Chair of the Board after his retirement date.

🗳️ Proposal One: Electing the Director 👑

The first matter up for vote is the election of a Class III director. The company recommends voting FOR the election of John T. (Jack) McDonald.

• Role: Mr. McDonald, the founder, is nominated to serve as the Class III director until the third annual meeting of stockholders following the election.
• Voting Detail: The vote requires the nominee to receive the highest number of affirmative votes from the combined Common Stock and Series A Preferred Stock shares.

💰 Proposal Three: Advisory Vote on Executive Compensation 💵

Stockholders will vote on an advisory basis to approve the compensation of the company's named executive officers (NEOs).

• Advisory Meaning: This is important to note because an advisory vote result is not legally binding on the company or the Board.
• Oversight: The Compensation Committee, chaired by David D. May, is responsible for reviewing and determining the compensation for all executive officers and directors.

💹 Proposal Four: Reverse Stock Split Proposal 📉

This proposal allows the Board to amend the Certificate of Incorporation to effect a "Reverse Split" of the Common Stock.

• Purpose: The split ratio will be in the range of 1-for-five to 1-for-30. A reverse split means that multiple shares of stock are consolidated into one share (e.g., five shares become one).
• Why this matters: Companies often use reverse splits to maintain a higher share price, which can be important for listing requirements on major exchanges.

💵 Executive Compensation Details 📈

The Compensation Committee provides detailed compensation data for the three named executive officers (NEOs): John T. McDonald, Michael D. Hill, and Daniel Doman.

• John T. McDonald's Compensation: In 2025, his total compensation was $4,774,820. In 2024, it was $3,903,514.
• Michael D. Hill's Compensation: In 2025, his total compensation was $617,800. In 2024, it was $790,382.
• Daniel Doman's Compensation: In 2025, his total compensation was $1,734,417.
• Outstanding Equity: The filing meticulously details outstanding, unvested equity awards for each NEO as of December 31, 2025, showing the current market value of these rights.

🛡️ Board Risk Management and Guidelines 🚨

The Board has established formal protocols to manage the various risks the company faces, which gives the Board its oversight teeth.

• Oversight Scope: The Audit Committee oversees financial and operational risks, including cybersecurity. The Compensation Committee oversees risks related to executive compensation. The Nominating and Governance Committee oversees corporate governance risks.
• Policies: The Board has adopted a written Code of Business Conduct and Ethics, which applies to all directors, officers, and employees.
• Clawbacks: The Compensation Committee has a clawback policy in place to recover incentive compensation if the company must restate its financial statements due to material noncompliance.

📧 Contact and Resources 📞

For stockholders needing more information, the company has designated specific contacts for various inquiries.

• General Annual Meeting Questions: Contact Investor Relations at (512) 960-1031.
• Stock Ownership for Registered Holders: Contact Broadridge Corporate Issuer Solutions, Inc. at (866) 321-8022.
• Proxy Materials: The full proxy materials, the Proxy Statement, and the Annual Report on Form 10-K are available at www.proxyvote.com.

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🧠 The Analogy

Voting on a Proxy Statement is like reviewing the minutes and bylaws for a large homeowners' association (HOA) that runs a multi-million dollar property. You aren't making day-to-day decisions, but you are voting on huge structural changes—like whether the association should make its primary pool, clubhouse, or parking structure smaller and consolidate it (the reverse split), or how the management fees (executive compensation) should be structured for the next year. Each section of the filing is designed to inform you on who is making the rules and how those rules will impact the value of your investment.

🧩 Final Takeaway

Upland is presenting its stockholders with significant governance decisions, most notably a potential reverse stock split and a substantial increase in the employee equity pool. While the founder, John T. McDonald, is stepping down from the CEO role, the Board structure remains highly detailed and robust, emphasizing rigorous independent oversight through its standing committees.