Form 4: Upland Software CFO's Tax-Related Stock Transaction

Upland Software's CFO, Michael Douglass Hill, reported a disposition of 8,856 shares of common stock to cover tax withholding obligations related to restricted stock unit vesting.

Summary

• Michael Douglass Hill, CFO, Treasurer & Secretary, and Director of Upland Software, Inc. (UPLD), reported a transaction on December 16, 2025.
• The transaction involved the disposition of 8,856 shares of common stock at a price of $1.485 per share.
• These shares were withheld by the issuer to satisfy tax withholding obligations in connection with the vesting of restricted stock units.
• This was not an open market sale of securities.
• Following the transaction, Michael Douglass Hill directly beneficially owns 331,222 shares of common stock.
• Additionally, 160,042 shares are indirectly beneficially owned through the MDH Trust, for which the reporting person is the trustee.

Sentiment

Score: 5

Explanation: The filing reports a routine, non-discretionary transaction related to executive compensation and tax obligations, indicating a neutral sentiment regarding the company's operational or financial performance.

Future Outlook

This filing does not contain any forward-looking statements or guidance regarding the company's future outlook.

Industry Context

The reported transaction is a routine insider filing (Form 4) detailing the disposition of shares to cover tax liabilities associated with the vesting of restricted stock units. This is a common and expected event for executives receiving equity compensation and does not typically reflect discretionary trading activity or a change in management's sentiment towards the company's stock.

Comparison to Industry Standards

• The practice of withholding shares to cover tax obligations upon the vesting of restricted stock units is a standard industry practice for equity compensation plans across publicly traded companies.
• This mechanism is widely used to manage the tax implications for employees and executives receiving stock-based awards, aligning with compensation structures seen in technology and software companies comparable to Upland Software.

Related Party Transactions

• Michael Douglass Hill indirectly beneficially owns 160,042 shares of common stock through the MDH Trust, for which he is the trustee and which holds shares for the benefit of his family.

Stakeholder Impact

• Shareholders: Minimal impact, as this is a routine tax-related transaction and not a discretionary sale, thus not indicative of management's sentiment on the stock price.
• Employees: No direct impact on the broader employee base, as this relates to executive compensation.

Key Dates

Keywords

Upland Software, UPLD, Form 4, Insider Transaction, CFO, Restricted Stock Units, Tax Withholding, Equity Compensation