Form 4: Upland Software CEO John McDonald Reports Stock Transaction

Upland Software CEO John T. McDonald reported the withholding of 19,677 shares of common stock to cover tax obligations related to restricted stock unit vesting.

Summary

• John T. McDonald, CEO and Director of Upland Software, Inc. (UPLD), reported a transaction on December 16, 2025.
• The transaction involved the withholding of 19,677 shares of Common Stock by the issuer.
• These shares were withheld to satisfy tax withholding obligations in connection with the vesting of restricted stock units, and it was not an open market sale of securities.
• The shares were valued at $1.485 per share for the withholding purpose.
• Following this transaction, Mr. McDonald directly beneficially owns 2,409,492 shares of Common Stock.
• Additionally, Mr. McDonald indirectly beneficially owns 363,738 shares through National Financial Services as Cust FBO J. McDonald RRA.
• The reported beneficial ownership does not include 125,000 shares of common stock held in a trust for the benefit of Mr. McDonald's children, where The Bryn Mawr Trust Company of Delaware is the trustee.

Sentiment

Score: 5

Explanation: The filing reports a routine insider transaction related to tax withholding upon RSU vesting, which is a neutral event for company operations or strategic direction.

Positives

• Vesting of restricted stock units (RSUs) indicates earned compensation for the CEO.

Negatives

• 19,677 shares were withheld by the issuer to satisfy tax withholding obligations, reducing the CEO's direct beneficial ownership. This is a mechanical tax event, not a discretionary sale.

Future Outlook

NA

Industry Context

NA

Related Party Transactions

• 125,000 shares of common stock are held in a trust for the benefit of Mr. McDonald's children, with The Bryn Mawr Trust Company of Delaware as trustee. These shares are not included in the reported beneficial ownership.

Stakeholder Impact

• Shareholders: A minor reduction in direct beneficial ownership by the CEO due to tax withholding, which is a standard operational event and not indicative of a discretionary sale.

Key Dates

Recommendation

This Form 4 filing details a routine tax withholding event related to the vesting of restricted stock units for the CEO. It does not provide new information regarding the company's operational performance, strategic direction, or financial health that would warrant a change in investment recommendation. The transaction is a standard part of executive compensation and tax management.

Keywords

Upland Software, UPLD, Form 4, insider transaction, stock withholding, CEO, John T. McDonald, restricted stock units, RSU vesting