Upland Software's three largest insider shareholders as of May 23, 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 |
| Stephen E Courter | - | 124,232 | 0 | 29 Oct, 2025 |
| Michael Douglass Hill | Cfo, Treasurer Secretary | 392,291 | 0 | 17 Mar, 2026 |
| Karen Cummings | President And Coo | 306,432 | 0 | 01 Jul, 2025 |
| Matthew Harnden Smith | General Counsel And Secretary | 131,908 | 0 | 17 Jun, 2025 |
| David May | - | 191,437 | 0 | 29 Oct, 2025 |
| David H S Chung | - | 124,484 | 0 | 29 Oct, 2025 |
| Rodney C Favaron | President | 338,742 | 0 | 21 Jun, 2022 |
| Timothy Mattox | Co President Coo | 419,008 | 0 | 29 Oct, 2025 |
| Kinloch Iii Gill | Clo And Secretary | 194,590 | 0 | 19 Sep, 2023 |
| Joe Ross | - | 118,545 | 0 | 02 Aug, 2023 |
| Teresa Miles Walsh | - | 144,490 | 0 | 29 Oct, 2025 |
| Dan Doman | Chief Operating Product Ofcr | 923,766 | 0 | 17 Mar, 2026 |
| Ian Burk | Chief Business Officer | 107,047 | 0 | 19 Dec, 2022 |
| Paul Kenneth Miller | Chief Operating Officer | 209,387 | 0 | 19 Dec, 2023 |
| Oliver Robert Macfarlane Yates | Chief Sales Officer | 251,567 | 0 | 19 Mar, 2024 |
| Matthew Breslin | Chief Revenue Officer | 150,000 | 0 | 07 Feb, 2024 |
* 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 | Dan Doman | Common Stock | D | 24,595 | $1.49 | 707,257 | D | F |
| 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 |
| 27 Oct, 2025 | Teresa Miles Walsh | Common Stock | A | 25,000 | $0.00 | 144,490 | D | A |
| 27 Oct, 2025 | David May | Common Stock | A | 25,000 | $0.00 | 191,437 | D | A |
| 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 | Timothy Mattox | Common Stock | A | 25,000 | $0.00 | 419,008 | D | A |
| 27 Oct, 2025 | Stephen E Courter | Common Stock | A | 25,000 | $0.00 | 124,232 | D | A |
| 16 Sep, 2025 | John T Mcdonald | Common Stock | D | 22,956 | $2.48 | 2,429,169 | D | F |
| 16 Sep, 2025 | Michael Douglass Hill | Common Stock | D | 11,152 | $2.48 | 340,078 | D | F |
| 16 Sep, 2025 | Dan Doman | Common Stock | D | 26,236 | $2.48 | 731,852 | 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 |