Upland Software's three largest insider shareholders as of April 11, 2026 are John T Mcdonald (Ceo, 2.39Mn shares), Dan Doman (Chief Operating Product Ofcr, 923.77K shares), Timothy Mattox (Co President Coo, 419.01K shares).
| Holder | Position | Shares (Direct) | Shares (Indirect) | Report Date |
|---|---|---|---|---|
| John T Mcdonald | Ceo | 2,390,887 | 0 | 17 Mar, 2026 |
| Dan Doman | Chief Operating Product Ofcr | 923,766 | 0 | 17 Mar, 2026 |
| Timothy Mattox | Co President Coo | 419,008 | 0 | 29 Oct, 2025 |
| Michael Douglass Hill | Cfo, Treasurer Secretary | 392,291 | 0 | 17 Mar, 2026 |
| John T Mcdonald | Ceo | 0 | 363,738 | 12 Aug, 2024 |
| Rodney C Favaron | President | 338,742 | 0 | 21 Jun, 2022 |
| Karen Cummings | President And Coo | 306,432 | 0 | 01 Jul, 2025 |
| Oliver Robert Macfarlane Yates | Chief Sales Officer | 251,567 | 0 | 19 Mar, 2024 |
| Paul Kenneth Miller | Chief Operating Officer | 209,387 | 0 | 19 Dec, 2023 |
| Kinloch Iii Gill | Clo And Secretary | 194,590 | 0 | 19 Sep, 2023 |
| David May | - | 191,437 | 0 | 29 Oct, 2025 |
| Michael Douglass Hill | Cfo Treasurer | 0 | 160,042 | 14 Jan, 2022 |
| Matthew Breslin | Chief Revenue Officer | 150,000 | 0 | 07 Feb, 2024 |
| Teresa Miles Walsh | - | 144,490 | 0 | 29 Oct, 2025 |
| Matthew Harnden Smith | General Counsel And Secretary | 131,908 | 0 | 17 Jun, 2025 |
| David H S Chung | - | 124,484 | 0 | 29 Oct, 2025 |
| Stephen E Courter | - | 124,232 | 0 | 29 Oct, 2025 |
| Joe Ross | - | 118,545 | 0 | 02 Aug, 2023 |
| Ian Burk | Chief Business Officer | 107,047 | 0 | 19 Dec, 2022 |
* Please note that the shares above only reflect shares from the fund portfolio and the institutional portfolio. Shares from the personal portfolio are excluded from this Institutional Ownership Page. See these insiders' latest transactions here on Insider Page.
| Transaction Date | Insider Name | Security Class | Transaction Type | Shares Traded | Price | Shares Remaining | Ownership | Code |
|---|---|---|---|---|---|---|---|---|
| 16 Mar, 2026 | John T Mcdonald | Common Stock | D | 18,605 | $0.54 | 2,390,887 | D | F |
| 16 Mar, 2026 | Michael Douglass Hill | Common Stock | D | 8,931 | $0.54 | 392,291 | D | F |
| 16 Mar, 2026 | Dan Doman | Common Stock | D | 33,491 | $0.54 | 923,766 | D | F |
| 27 Feb, 2026 | Dan Doman | Common Stock | A | 100,000 | $0.00 | 957,257 | D | A |
| 23 Feb, 2026 | Michael Douglass Hill | Common Stock | A | 70,000 | $0.00 | 401,222 | D | A |
| 23 Feb, 2026 | Dan Doman | Common Stock | A | 150,000 | $0.00 | 857,257 | D | A |
| 16 Dec, 2025 | John T Mcdonald | Common Stock | D | 19,677 | $1.49 | 2,409,492 | D | F |
| 16 Dec, 2025 | Michael Douglass Hill | Common Stock | D | 8,856 | $1.49 | 331,222 | D | F |
| 16 Dec, 2025 | Dan Doman | Common Stock | D | 24,595 | $1.49 | 707,257 | D | F |
| 27 Oct, 2025 | David H S Chung | Common Stock | A | 25,000 | $0.00 | 124,484 | D | A |
| 27 Oct, 2025 | Teresa Miles Walsh | Common Stock | A | 25,000 | $0.00 | 144,490 | D | A |
| 27 Oct, 2025 | Stephen E Courter | Common Stock | A | 25,000 | $0.00 | 124,232 | D | A |
| 27 Oct, 2025 | Timothy Mattox | Common Stock | A | 25,000 | $0.00 | 419,008 | D | A |
| 27 Oct, 2025 | David May | Common Stock | A | 25,000 | $0.00 | 191,437 | D | A |
| 16 Sep, 2025 | John T Mcdonald | Common Stock | D | 22,956 | $2.48 | 2,429,169 | D | F |
| 16 Sep, 2025 | Dan Doman | Common Stock | D | 26,236 | $2.48 | 731,852 | D | F |
| 16 Sep, 2025 | Michael Douglass Hill | Common Stock | D | 11,152 | $2.48 | 340,078 | D | F |
| 11 Sep, 2025 | John T Mcdonald | Common Stock | D | 14,438 | $2.36 | 2,452,125 | D | S |
| 30 Jun, 2025 | Karen Cummings | Common Stock | D | 40,993 | $1.95 | 306,432 | D | F |
| 13 Jun, 2025 | Dan Doman | Common Stock | A | 350,000 | $0.00 | 772,846 | D | A |