Upland Software, Inc. (UPLD) Insider Trading
Directors, officers and holders of more than 10% of UPLD report their trades in its stock on SEC Form 4, within two business days. Each row below is one Form 4 transaction line. The one-letter code says what kind of transaction it was: only P (purchase) and S (sale) are open-market or private trades; awards, option exercises, tax withholding and gifts carry other codes.
Recent Form 4 transactions
The 50 most recent of 90 transactions on file: 0 with code P, 8 with code S and 42 with other codes.
| Date | Insider | Title | Code | Shares | Price | Value |
|---|---|---|---|---|---|---|
| Sep 16, 2026 | Nathaniel Sean | CEO and President | F Tax Payment | 1,640 | $3.94 | $6,470 |
| Sep 16, 2026 | Simon Jennifer L. | Chief Financial Officer | F Tax Payment | 1,117 | $3.94 | $4,407 |
| Sep 16, 2026 | Doman Dan | Chief Operating & Product Ofcr | F Tax Payment | 2,952 | $3.94 | $11,646 |
| Aug 17, 2026 | Simon Jennifer L. | Chief Financial Officer | A Award | 30,000 | Not measured | Not measured |
| Aug 17, 2026 | Simon Jennifer L. | Chief Financial Officer | A Award | 6,666 | Not measured | Not measured |
| Aug 7, 2026 | Mattox Timothy | Director | S Sale | 847 | $4.28 | $3,627 |
| Aug 6, 2026 | Mattox Timothy | Director | S Sale | 1,000 | $4.27 | $4,270 |
| Aug 5, 2026 | Mattox Timothy | Director | S Sale | 1,000 | $4.53 | $4,530 |
| Aug 4, 2026 | Mattox Timothy | Director | S Sale | 1,000 | $4.33 | $4,330 |
| Aug 3, 2026 | Mattox Timothy | Director | S Sale | 1,000 | $4.45 | $4,450 |
| Jul 31, 2026 | Mattox Timothy | Director | S Sale | 1,000 | $4.48 | $4,480 |
| Jun 16, 2026 | Doman Dan | Chief Operating & Product Ofcr | F Tax Payment | 2,952 | $6.06 | $17,898 |
| Jun 16, 2026 | Nathaniel Sean | CEO and President | F Tax Payment | 1,861 | $6.06 | $11,282 |
| Jun 16, 2026 | Hill Michael Douglass | CFO, Treasurer & Secretary | F Tax Payment | 893 | $6.06 | $5,416 |
| Jun 4, 2026 | Nathaniel Sean | CEO and President | A Award | 50,000 | Not measured | Not measured |
| Jun 4, 2026 | Nathaniel Sean | CEO and President | A Award | 133,333 | Not measured | Not measured |
| Apr 30, 2026 | MCDONALD JOHN T | CEO | D Disposition | 250,000 | Not measured | Not measured |
| Apr 30, 2026 | MCDONALD JOHN T | CEO | A Award | 25,000 | Not measured | Not measured |
| Mar 16, 2026 | MCDONALD JOHN T | CEO | F Tax Payment | 1,861 | $5.40 | $10,047 |
| Mar 16, 2026 | Hill Michael Douglass | CFO, Treasurer & Secretary | F Tax Payment | 893 | $5.40 | $4,823 |
| Mar 16, 2026 | Doman Dan | Chief Operating & Product Ofcr | F Tax Payment | 3,349 | $5.40 | $18,085 |
| Feb 27, 2026 | Doman Dan | Chief Operating & Product Ofcr | A Award | 10,000 | Not measured | Not measured |
| Feb 23, 2026 | Doman Dan | Chief Operating & Product Ofcr | A Award | 15,000 | Not measured | Not measured |
| Feb 23, 2026 | Hill Michael Douglass | CFO, Treasurer & Secretary | A Award | 7,000 | Not measured | Not measured |
| Dec 16, 2025 | MCDONALD JOHN T | CEO | F Tax Payment | 1,968 | $14.85 | $29,220 |
| Dec 16, 2025 | Doman Dan | Chief Operating & Product Ofcr | F Tax Payment | 2,460 | $14.85 | $36,524 |
| Dec 16, 2025 | Hill Michael Douglass | CFO, Treasurer & Secretary | F Tax Payment | 886 | $14.85 | $13,151 |
| Oct 27, 2025 | MAY DAVID | Director | A Award | 2,500 | Not measured | Not measured |
| Oct 27, 2025 | Walsh Teresa Miles | Director | A Award | 2,500 | Not measured | Not measured |
| Oct 27, 2025 | Mattox Timothy | Director | A Award | 2,500 | Not measured | Not measured |
| Oct 27, 2025 | COURTER STEPHEN E | Director | A Award | 2,500 | Not measured | Not measured |
| Oct 27, 2025 | Chung David H S | Director | A Award | 2,500 | Not measured | Not measured |
| Sep 16, 2025 | Hill Michael Douglass | CFO, Treasurer & Secretary | F Tax Payment | 1,115 | $24.80 | $27,657 |
| Sep 16, 2025 | Doman Dan | Chief Operating & Product Ofcr | F Tax Payment | 2,624 | $24.80 | $65,065 |
| Sep 16, 2025 | MCDONALD JOHN T | CEO | F Tax Payment | 2,296 | $24.80 | $56,931 |
| Sep 11, 2025 | MCDONALD JOHN T | CEO | S Sale | 1,444 | $23.59 | $34,064 |
| Jun 30, 2025 | Cummings Karen | President and COO | F Tax Payment | 4,099 | $19.50 | $79,936 |
| Jun 16, 2025 | Cummings Karen | President and COO | F Tax Payment | 1,148 | $18.40 | $21,121 |
| Jun 16, 2025 | MCDONALD JOHN T | CEO | F Tax Payment | 2,296 | $18.40 | $42,241 |
| Jun 16, 2025 | Hill Michael Douglass | CFO, Treasurer & Secretary | F Tax Payment | 1,115 | $18.40 | $20,520 |
| Jun 16, 2025 | Doman Dan | Chief Operating & Product Ofcr | F Tax Payment | 1,476 | $18.40 | $27,155 |
| Jun 16, 2025 | Smith Matthew Harnden | General Counsel and Secretary | F Tax Payment | 360 | $18.40 | $6,617 |
| Jun 13, 2025 | Doman Dan | Chief Operating & Product Ofcr | A Award | 35,000 | Not measured | Not measured |
| Mar 17, 2025 | Mattox Timothy | Director | S Sale | 2,000 | $31.93 | $63,862 |
| Mar 16, 2025 | Hill Michael Douglass | CFO, Treasurer & Secretary | F Tax Payment | 1,265 | $31.00 | $39,224 |
| Mar 16, 2025 | Smith Matthew Harnden | General Counsel and Secretary | F Tax Payment | 414 | $31.00 | $12,819 |
| Mar 16, 2025 | MCDONALD JOHN T | CEO | F Tax Payment | 2,427 | $31.00 | $75,246 |
| Mar 16, 2025 | Cummings Karen | President and COO | F Tax Payment | 865 | $31.00 | $26,809 |
| Mar 16, 2025 | Doman Dan | Chief Operating & Product Ofcr | F Tax Payment | 1,641 | $31.00 | $50,883 |
| Jan 28, 2025 | Smith Matthew Harnden | General Counsel and Secretary | A Award | 5,000 | Not measured | Not measured |
The full Form 4 history is on the UPLD company page (Insider Trades card, View all).
Questions about this data
Which insider transactions are open-market trades?
Code P (open market or private purchase) and code S (open market or private sale). Code F is shares withheld to pay tax on vesting stock, A is an award from the company, M and X are option exercises and G is a gift. None of those is the insider choosing to buy or sell in the market.
How quickly are insider trades reported?
A Form 4 is due before the end of the second business day after the trade. The date shown is the transaction date from the form.
Who has to file Form 4?
Officers, directors and beneficial owners of more than 10% of a class of the company’s registered equity, under Section 16 of the Securities Exchange Act.
Look up any code in the Form 4 transaction code reference, or read Form 4 codes explained.