Form 4: Upland Software CEO's RSU Tax Obligation Met

Upland Software CEO John T. McDonald had 22,956 shares withheld by the company to cover tax obligations from restricted stock unit vesting.

Summary

• John T. McDonald, CEO and Director of Upland Software, Inc. (UPLD), reported a transaction on September 16, 2025.
• The transaction involved the disposition of 22,956 shares of Common Stock at a price of $2.48 per share.
• These shares were withheld by the issuer to satisfy tax withholding obligations in connection with the vesting of restricted stock units.
• The filing explicitly states this was not an open market sale of securities.
• Following this transaction, Mr. McDonald directly beneficially owns 2,429,169 shares of Common Stock.
• Additionally, 363,738 shares are indirectly beneficially owned via National Financial Services as Custodian FBO J. McDonald RRA.
• The reported beneficial ownership does not include 125,000 shares held in a trust for the benefit of Mr. McDonald's children.

Sentiment

Score: 5

Explanation: The filing reports a routine, non-discretionary transaction (tax withholding for RSU vesting) which is neutral in sentiment. It is neither a voluntary sale nor a purchase, and the clarification that it's not an open market sale helps mitigate potential negative interpretations.

Positives

• The transaction clarifies that the disposition of shares was for tax withholding related to RSU vesting, not a voluntary open market sale, which can prevent negative market speculation.
• The vesting of restricted stock units indicates continued compensation and alignment of the executive's interests with shareholders.

Negatives

• A total of 22,956 shares of Common Stock were disposed of, resulting in a reduction of Mr. McDonald's direct beneficial ownership.

Future Outlook

NA

Industry Context

NA

Stakeholder Impact

• Shareholders: Minimal impact as this is a routine, non-discretionary transaction for tax purposes, not a voluntary sale indicating a change in management's confidence.
• Employees: No direct impact mentioned.

Key Dates

Keywords

Upland Software, UPLD, Form 4, Insider Transaction, Restricted Stock Units, RSU, Tax Withholding, John T. McDonald, CEO, Director