Every Form 4 that Upland Software, Inc. (UPLD) has filed with the SEC in the last 12 months is listed below, newest first, and each one links through to the document itself with the summary and the scores our analysis gives it.
A Form 4 covers the transactions officers, directors and large holders report, so if you follow UPLD and want that one kind of document rather than the whole filing history, this is the page to keep. The company's other filings, of every form, are on the full UPLD filings page.
Upland Software, Inc. (UPLD) reported that officer Dan Doman, Chief Operating & Product Officer, had 2,952 shares of common stock withheld on September 16, 2026 to satisfy tax withholding obligations related to vesting restricted stock units. This was not an open market sale. After this withholding, Doman directly holds 86,473 shares of Upland common stock.
Upland Software, Inc. (UPLD) reported that CEO and President Nathaniel Sean had 1,640 shares of common stock withheld on September 16, 2026 to satisfy tax withholding obligations upon vesting of restricted stock units. The shares were withheld by the issuer and were not an open market sale. Following this transaction, Sean directly held 48,574 shares of Upland Software common stock. No transactions were made under a Rule 10b5-1 trading plan.
Upland Software, Inc. (UPLD) reported that its Chief Financial Officer Jennifer L. Simon had 1,117 shares of common stock withheld on September 16, 2026 to satisfy tax withholding obligations related to vesting of restricted stock units. After this withholding, she directly holds 28,883 shares of Upland common stock. The company notes this was not an open market sale of securities.
Upland Software, Inc. (symbol: UPLD) is the issuer of record for a Form 4 filing submitted to the SEC.
Upland Software, Inc. director Timothy Mattox reported selling 847.4 shares of common stock on 2026-08-07 in an open market or private transaction at a weighted average price of $4.2801 per share. The sale was made under an approved Rule 10b5-1 trading plan adopted on 03/09/2026, and his directly held stake after the sale was 36,052.6 shares.
Upland Software, Inc. director Timothy Mattox reported a sale of 1,000 shares of common stock on 2026-08-06 at $4.27 per share in an open-market or private transaction. After this sale, he holds 36,900 shares directly. The transaction was conducted under an approved Rule 10b5-1 trading plan with an adoption date of 03/09/2026.
Upland Software, Inc. director Timothy Mattox reported two sales of company common stock totaling 2,000 shares. He sold 1,000 shares at $4.33 on 2026-08-04 and 1,000 shares at $4.53 on 2026-08-05. Both transactions were conducted under an approved 10b5-1 Plan adopted on 03/09/2026.
Upland Software, Inc. director Timothy Mattox reported two sales of common stock totaling 2,000 shares, with 1,000 shares sold at $4.48 on 2026-07-31 and 1,000 shares at $4.45 on 2026-08-03. According to the footnotes, these transactions were conducted under an approved 10b5-1 Plan adopted on 03/09/2026 and the shares were sold to cover tax withholding obligations arising from the vesting of restricted stock units.
Upland Software, Inc. reported a Form 4 for CFO, Treasurer & Secretary Michael Douglass Hill. On June 16, 2026, 8,931 shares of common stock were disposed of at $0.6064 per share to satisfy tax withholding obligations tied to vesting restricted stock units, which is not an open-market sale. After this tax-withholding disposition, Hill directly holds 383,360 common shares and indirectly holds 160,042 common shares through the MDH Trust, where he serves as trustee for his family.
Upland Software, Inc. CEO and President Nathaniel Sean reported a routine tax-related share disposition. On 2026-06-16, 18,605 shares of common stock were withheld by the company to cover tax obligations from vesting restricted stock units, at $0.6064 per share. This was explicitly described as not being an open market sale. After the withholding, Sean directly held 502,146 shares of Upland Software common stock.
Upland Software, Inc. Chief Operating & Product Officer Dan Doman reported a routine tax-related share disposition. On June 16, 2026, 29,515 shares of common stock were withheld by the company at $0.6064 per share to cover tax obligations from vesting restricted stock units. This was explicitly stated as not being an open-market sale. After this withholding, Doman directly holds 894,251 shares of Upland Software common stock.
Nathaniel Sean reported acquisition or exercise transactions in this Form 4 filing.
Upland Software CEO Nathaniel Sean received new equity awards. He was granted 500,000 shares of common stock at no cost, bringing his direct holdings to 520,751 shares. He was also granted 133,333 performance-based restricted stock units tied to stock-price hurdles between $2.00 and $5.00 over a three-year period, with time-based RSUs vesting quarterly from June 16, 2026 and potential acceleration after certain terminations following a Change in Control.
Upland Software director John T. McDonald reported equity compensation changes involving common stock and performance share units. He received a grant of 250,000 restricted stock units, which will vest on the earliest of February 28, 2028, his termination from the board without Cause as defined in his employment agreement, or a Change in Control under the company’s 2024 Omnibus Incentive Plan. At the same time, 250,000 performance stock units were canceled effective April 30, 2026 under a Transition Agreement between McDonald and the company. Following these transactions, he holds 2,640,887 shares of common stock directly and 363,738 shares indirectly through a custodial account, in addition to 125,000 shares held in a trust for his children that are noted but not included in the reported totals.
Upland Software CEO John T. McDonald reported a routine tax-related share disposition. On the vesting of restricted stock units, 18,605 shares of Common Stock were withheld by the company at $0.54 per share to cover tax obligations, which the filing specifies is not an open market sale. After this withholding, McDonald directly owns 2,390,887 shares of Upland Software common stock. He also has an additional 363,738 shares held indirectly through an account at National Financial Services, and a footnote notes a separate 125,000 shares held in a trust for his children.
Upland Software, Inc. CFO, Treasurer & Secretary Michael Douglass Hill reported a routine tax-related share disposition. On March 16, 2026, 8,931 shares of common stock were withheld by the company at $0.54 per share to cover tax obligations from vesting restricted stock units. This was explicitly described as not an open-market sale. After this withholding, Hill directly owned 392,291 common shares and indirectly held 160,042 shares through the MDH Trust, where he serves as trustee for his family.
Upland Software, Inc. Chief Operating & Product Officer Dan Doman reported a routine tax-related share disposition. On the reported date, 33,491 shares of common stock were withheld by the company at a price of $0.54 per share to cover tax obligations tied to vesting restricted stock units. This was explicitly described as not being an open-market sale. After the withholding, Doman directly owned 923,766 shares of Upland common stock, indicating he continues to hold a substantial equity position in the company.
Upland Software, Inc. reported that Chief Operating & Product Officer Dan Doman acquired 100,000 shares of common stock through a grant of restricted stock units. The award was priced at $0.00 per share, increasing his directly held stake to 957,257 shares.
The restricted stock units vest in twelve equal quarterly installments starting on the three‑month anniversary of the vesting commencement date of December 16, 2025, with potential accelerated vesting under certain change‑of‑control conditions.
Hill Michael Douglass reported acquisition or exercise transactions in this Form 4 filing.
Upland Software’s CFO, Treasurer & Secretary Michael Douglass Hill received an equity grant of 70,000 shares of common stock on February 23, 2026. The award was made at a stated price of $0.00 per share as a grant, not an open‑market purchase.
According to a footnote, these restricted stock units vest in twelve equal quarterly installments starting on the three‑month anniversary of the Vesting Commencement Date of December 16, 2025, subject to continued service or as otherwise specified in his executive employment agreement. Following the grant, Hill directly owns 401,222 common shares. He also has indirect ownership of 160,042 common shares held by the MDH Trust, a trust for the benefit of his family for which he serves as trustee.
Doman Dan reported acquisition or exercise transactions in this Form 4 filing.
Upland Software’s Chief Operating & Product Officer Dan Doman received an equity award of 150,000 shares of common stock at a stated price of $0.00 per share. After this grant, his directly held stake increased to 857,257 shares.
According to the accompanying footnote, these are restricted stock units that vest in twelve equal quarterly installments starting on the three‑month anniversary of a vesting commencement date of December 16, 2025. Vesting requires Mr. Doman to remain a service provider through each vesting date, except as otherwise provided in his executive employment agreement.
Upland Software, Inc. reported that its Chief Operating & Product Officer, D. Doman, had 24,595 shares of common stock withheld on 12/16/2025 at $1.485 per share to cover tax obligations tied to the vesting of restricted stock units. The filing states this was not an open market sale, but shares retained by the issuer for tax withholding. After this transaction, Doman beneficially owned 707,257 shares of Upland Software common stock directly.
Upland Software, Inc. CEO and director J. McDonald reported an automatic share withholding related to equity compensation. On 12/16/2025, 19,677 shares of Upland common stock were withheld by the company at a price of $1.485 per share to cover tax obligations tied to the vesting of restricted stock units, and the filing clarifies this was not an open market sale. After this transaction, McDonald beneficially owned 2,409,492 shares directly and 363,738 shares indirectly through National Financial Services as custodian for a retirement account. The disclosure also notes that these totals do not include 125,000 additional shares held in a trust for the benefit of McDonald’s children.
Upland Software, Inc. officer Micheal D. Hill, who serves as CFO, Treasurer and Secretary, reported an insider transaction involving company common stock. On 12/16/2025, 8,856 shares of common stock were disposed of at $1.485 per share with a transaction code "F," indicating shares were withheld by the issuer to satisfy tax withholding obligations tied to the vesting of restricted stock units, rather than sold in the open market.
Following this tax withholding event, Hill beneficially owned 331,222 shares of common stock directly. In addition, 160,042 shares were held indirectly through the MDH Trust, a trust for the benefit of his family for which he serves as trustee.
Upland Software (UPLD) director D. Chung reported a grant of 25,000 restricted stock units on 10/27/2025 at a stated price of $0. Half of the RSUs vest on 12/16/2025, with the remaining units vesting in two equal installments on 3/16/2026 and 6/16/2026, contingent on continued board service.
After the grant, Chung beneficially owns 124,484 shares directly. Any proceeds from later sales of shares covered by these RSUs will be transferred to HGGC pursuant to an agreement, and Chung disclaims all pecuniary interest in the reported securities.
Upland Software (UPLD) reported an insider equity grant. A director acquired 25,000 restricted stock units on 10/27/2025 at $0. The RSUs vest as follows: one‑half on 12/16/2025, and the remainder in two equal quarterly installments on 3/16/2026 and 6/16/2026. Following this transaction, the director beneficially owned 124,232 shares, held directly.
Upland Software (UPLD) director T. Mattox reported acquiring 25,000 shares of Common Stock via restricted stock units on 10/27/2025 at a price of $0 per share, according to a Form 4.
The RSUs vest as follows: one-half on 12/16/2025, and the remainder in two equal quarterly installments on 3/16/2026 and 6/16/2026.
Following this transaction, Mattox beneficially owned 419,008 shares, held directly.
Upland Software (UPLD) reported an insider equity award on a Form 4. A company director acquired 25,000 shares of common stock in the form of restricted stock units (RSUs) on 10/27/2025 at a stated price of $0 per unit.
The RSUs vest as disclosed: one-half on 12/16/2025, with the remainder vesting in two equal quarterly installments on 3/16/2026 and 6/16/2026. Following this transaction, the reporting person beneficially owned 191,437 shares. The ownership form is listed as Direct.
Upland Software (UPLD) reported an insider equity award. A director acquired 25,000 shares on 10/27/2025 at a reported price of $0, reflecting a grant of restricted stock units. Following the transaction, the director directly beneficially owns 144,490 shares.
The RSUs vest as follows: one-half on 12/16/2025, and the remainder in two equal installments on 3/16/2026 and 6/16/2026.