Upland Software's three largest insider shareholders as of September 29, 2026 are John T Mcdonald (Ceo, 264.09K shares), Dan Doman (Chief Operating Product Ofcr, 86.47K shares), Sean Nathaniel (Ceo And President, 48.57K shares).
| # | Insider | Position | Direct | Indirect | Total | Share of Insiders | Last Filed |
|---|---|---|---|---|---|---|---|
| 1 | John T Mcdonald | Ceo | 264,089 | 0 | 264,089 | 35.6% | 04 May, 2026 |
| 2 | Dan Doman | Chief Operating Product Ofcr | 86,473 | 0 | 86,473 | 11.7% | 21 Sep, 2026 |
| 3 | Sean Nathaniel | Ceo And President | 48,574 | 0 | 48,574 | 6.5% | 21 Sep, 2026 |
| 4 | Michael Douglass Hill | Cfo, Treasurer Secretary | 38,336 | 0 | 38,336 | 5.2% | 16 Jun, 2026 |
| 5 | Timothy Mattox | Co President Coo | 36,053 | 0 | 36,053 | 4.9% | 11 Aug, 2026 |
| 6 | Rodney C Favaron | President | 33,874 | 0 | 33,874 | 4.6% | 21 Jun, 2022 |
| 7 | Karen Cummings | President And Coo | 30,643 | 0 | 30,643 | 4.1% | 01 Jul, 2025 |
| 8 | Jennifer L. Simon | Chief Financial Officer | 28,883 | 0 | 28,883 | 3.9% | 21 Sep, 2026 |
| 9 | Oliver Robert Macfarlane Yates | Chief Sales Officer | 25,157 | 0 | 25,157 | 3.4% | 19 Mar, 2024 |
| 10 | Paul Kenneth Miller | Chief Operating Officer | 20,939 | 0 | 20,939 | 2.8% | 19 Dec, 2023 |
| 11 | Kinloch Iii Gill | Clo And Secretary | 19,459 | 0 | 19,459 | 2.6% | 19 Sep, 2023 |
| 12 | David May | Director | 19,144 | 0 | 19,144 | 2.6% | 29 Oct, 2025 |
| 13 | Matthew Breslin | Chief Revenue Officer | 15,000 | 0 | 15,000 | 2.0% | 07 Feb, 2024 |
| 14 | Teresa Miles Walsh | Director | 14,449 | 0 | 14,449 | 1.9% | 29 Oct, 2025 |
| 15 | Matthew Harnden Smith | General Counsel And Secretary | 13,191 | 0 | 13,191 | 1.8% | 17 Jun, 2025 |
| 16 | David H S Chung | Director | 12,448 | 0 | 12,448 | 1.7% | 29 Oct, 2025 |
| 17 | Stephen E Courter | Director | 12,423 | 0 | 12,423 | 1.7% | 29 Oct, 2025 |
| 18 | Joe Ross | Director | 11,855 | 0 | 11,855 | 1.6% | 02 Aug, 2023 |
| 19 | Ian Burk | Chief Business Officer | 10,705 | 0 | 10,705 | 1.4% | 19 Dec, 2022 |
Each row is that insider’s most recently reported position, from Form 4 filings over the last 60 months — which is why this total does not tie to the quarterly series above, where a quarter counts only the insiders who filed in it. Shares held through a fund or institutional portfolio are counted on the institutional ownership page instead.
| Date | Insider | Position | Transaction | Shares | Price | Value | Shares Held After | Ownership |
|---|---|---|---|---|---|---|---|---|
| 16 Sep, 2026 | Jennifer L. Simon | Chief Financial Officer | Disposed F | 1,117 | $3.95 | $4.41K | 28,883 | Direct |
| 16 Sep, 2026 | Sean Nathaniel | Ceo And President | Disposed F | 1,640 | $3.95 | $6.47K | 48,574 | Direct |
| 16 Sep, 2026 | Dan Doman | Chief Operating Product Ofcr | Disposed F | 2,952 | $3.95 | $11.65K | 86,473 | Direct |
| 17 Aug, 2026 | Jennifer L. Simon | Chief Financial Officer | Acquired A | 30,000 | $0.00 | $0 | 30,000 | Direct |
| 17 Aug, 2026 | Jennifer L. Simon | Chief Financial Officer | Acquired A | 6,666 | $0.00 | $0 | 6,666 | Direct |
| 07 Aug, 2026 | Timothy Mattox | Director | Disposed S | 847 | $4.28 | $3.63K | 36,053 | Direct |
| 06 Aug, 2026 | Timothy Mattox | Director | Disposed S | 1,000 | $4.27 | $4.27K | 36,900 | Direct |
| 04 Aug, 2026 | Timothy Mattox | Director | Disposed S | 1,000 | $4.33 | $4.33K | 38,900 | Direct |
| 05 Aug, 2026 | Timothy Mattox | Director | Disposed S | 1,000 | $4.53 | $4.53K | 37,900 | Direct |
| 31 Jul, 2026 | Timothy Mattox | Director | Disposed S | 1,000 | $4.48 | $4.48K | 40,900 | Direct |
| 03 Aug, 2026 | Timothy Mattox | Director | Disposed S | 1,000 | $4.45 | $4.45K | 39,900 | Direct |
| 16 Jun, 2026 | Michael Douglass Hill | Cfo, Treasurer Secretary | Disposed F | 8,931 | $6.06 | $54.16K | 38,336 | Direct |
| 16 Jun, 2026 | Sean Nathaniel | Ceo And President | Disposed F | 18,605 | $6.06 | $112.82K | 50,215 | Direct |
| 16 Jun, 2026 | Dan Doman | Chief Operating Product Ofcr | Disposed F | 29,515 | $6.06 | $178.98K | 89,425 | Direct |
| 04 Jun, 2026 | Sean Nathaniel | Ceo And President | Acquired A | 500,000 | $0.00 | $0 | 52,075 | Direct |
| 04 Jun, 2026 | Sean Nathaniel | Ceo And President | Acquired A | 133,333 | $0.00 | $0 | 13,333 | Direct |
| 30 Apr, 2026 | John T Mcdonald | Director | Acquired A | 250,000 | $0.00 | $0 | 264,089 | Direct |
| 30 Apr, 2026 | John T Mcdonald | Director | Disposed D | 250,000 | $0.00 | $0 | 0 | Direct |
| 16 Mar, 2026 | John T Mcdonald | Ceo | Disposed F | 18,605 | $5.40 | $100.47K | 239,089 | Direct |
| 16 Mar, 2026 | Dan Doman | Chief Operating Product Ofcr | Disposed F | 33,491 | $5.40 | $180.85K | 92,377 | Direct |