UPLD · Insider Trading
Upland Software, Inc.
Every open-market purchase and sale reported by UPLD officers, directors and 10%+ beneficial owners on SEC Form 4, which must be filed within two business days of the transaction. Sales often reflect scheduled 10b5-1 plans or tax withholding rather than a directional view, so read counts alongside the size and the filer.
| Filed | Insider | Role | Type | Shares | Value |
|---|---|---|---|---|---|
| 2026-09-21 | Sean Nathaniel | CEO and President | F | −1,640 | −$6.47K |
| 2026-09-21 | Dan Doman | Chief Operating & Product Ofcr | F | −2,952 | −$11.65K |
| 2026-09-21 | Jennifer L. Simon | Chief Financial Officer | F | −1,117 | −$4.41K |
| 2026-08-18 | Jennifer L. Simon | Chief Financial Officer | A | +30,000 | — |
| 2026-08-11 | Timothy Mattox | Director | Sell | −847 | −$3.63K |
| 2026-08-10 | Timothy Mattox | Director | Sell | −1,000 | −$4.27K |
| 2026-08-06 | Timothy Mattox | Director | Sell | −2,000 | −$8.86K |
| 2026-08-04 | Timothy Mattox | Director | Sell | −2,000 | −$8.93K |
| 2026-06-16 | Dan Doman | Chief Operating & Product Ofcr | F | −29,515 | −$17.90K |
| 2026-06-16 | Michael Douglass Hill | CFO, Treasurer & Secretary | F | −8,931 | −$5.42K |
| 2026-06-16 | Sean Nathaniel | CEO and President | F | −18,605 | −$11.28K |
| 2026-06-08 | Sean Nathaniel | CEO and President | A | +500,000 | — |
| 2026-05-04 | John T McDonald | Director | A | +250,000 | — |
| 2026-03-17 | Dan Doman | Chief Operating & Product Ofcr | F | −33,491 | −$18.09K |
| 2026-03-17 | Michael Douglass Hill | CFO, Treasurer & Secretary | F | −8,931 | −$4.82K |
| 2026-03-17 | John T McDonald | CEO | F | −18,605 | −$10.05K |
| 2026-03-03 | Dan Doman | Chief Operating & Product Ofcr | A | +100,000 | — |
| 2026-02-25 | Michael Douglass Hill | CFO, Treasurer & Secretary | A | +70,000 | — |
| 2026-02-25 | Dan Doman | Chief Operating & Product Ofcr | A | +150,000 | — |
| 2025-12-17 | John T McDonald | CEO | F | −19,677 | −$29.22K |
| 2025-12-17 | Michael Douglass Hill | CFO, Treasurer & Secretary | F | −8,856 | −$13.15K |
| 2025-12-17 | Dan Doman | Chief Operating & Product Ofcr | F | −24,595 | −$36.52K |
| 2025-10-29 | Teresa Miles Walsh | Director | A | +25,000 | — |
| 2025-10-29 | Stephen E Courter | Director | A | +25,000 | — |
| 2025-10-29 | Timothy Mattox | Director | A | +25,000 | — |
| 2025-10-29 | David May | Director | A | +25,000 | — |
| 2025-10-29 | David H S Chung | Director | A | +25,000 | — |
| 2025-09-17 | Michael Douglass Hill | CFO, Treasurer & Secretary | F | −11,152 | −$27.66K |
| 2025-09-17 | John T McDonald | CEO | F | −22,956 | −$56.93K |
| 2025-09-17 | Dan Doman | Chief Operating & Product Ofcr | F | −26,236 | −$65.07K |
| 2025-09-11 | John T McDonald | CEO | Sell | −14,438 | −$34.06K |
| 2025-07-01 | Karen Cummings | President and COO | F | −40,993 | −$79.94K |
| 2025-06-17 | Karen Cummings | President and COO | F | −11,479 | −$21.12K |
| 2025-06-17 | Michael Douglass Hill | CFO & Treasurer | F | −11,152 | −$20.52K |
| 2025-06-17 | John T McDonald | CEO | F | −22,957 | −$42.24K |
| 2025-06-17 | Matthew Harnden Smith | General Counsel and Secretary | F | −3,596 | −$6.62K |
| 2025-06-17 | Dan Doman | Chief Product Officer | MIXED | +335,242 | −$27.15K |
| 2025-03-17 | Dan Doman | Chief Product Officer | F | −16,414 | −$50.88K |
| 2025-03-17 | Timothy Mattox | Director | Sell | −20,000 | −$63.86K |
| 2025-03-17 | Karen Cummings | President and COO | F | −8,648 | −$26.81K |
| 2025-03-17 | Michael Douglass Hill | CFO & Treasurer | F | −12,653 | −$39.22K |
| 2025-03-17 | Matthew Harnden Smith | General Counsel and Secretary | F | −4,135 | −$12.82K |
| 2025-03-17 | John T McDonald | CEO | F | −24,273 | −$75.25K |
| 2025-01-30 | Matthew Harnden Smith | General Counsel and Secretary | A | +50,000 | — |
| 2025-01-30 | John T McDonald | CEO | A | +250,000 | — |
| 2025-01-30 | Dan Doman | Chief Product Officer | A | +150,000 | — |
| 2025-01-30 | Michael Douglass Hill | CFO & Treasurer | A | +70,000 | — |
| 2024-12-17 | Timothy Mattox | Director | Sell | −2,768 | −$12.61K |
| 2024-12-17 | Dan Doman | Chief Product Officer | F | −11,643 | −$52.51K |
| 2024-12-17 | Michael Douglass Hill | CFO & Treasurer | F | −11,070 | −$49.93K |
| Insider | Role | Shares Held | Value |
|---|---|---|---|
| John T McDonald | CEO | 300,463 | $1.15M |
| Dan Doman | Chief Operating & Product Ofcr | 86,473 | $329.89K |
| Michael Douglass Hill | CFO, Treasurer & Secretary | 54,340 | $207.31K |
| Sean Nathaniel | CEO and President | 48,574 | $185.31K |
| Timothy Mattox | Director | 36,052 | $137.54K |
| Karen Cummings | President and COO | 30,643 | $116.90K |
| Jennifer L. Simon | Chief Financial Officer | 28,883 | $110.19K |
| David May | Director | 19,144 | $73.03K |
| Teresa Miles Walsh | Director | 14,449 | $55.12K |
| Matthew Harnden Smith | General Counsel and Secretary | 13,191 | $50.32K |
| David H S Chung | Director | 12,448 | $47.49K |
| Stephen E Courter | Director | 12,423 | $47.39K |
Form 4 reports a change in beneficial ownership by an officer, director or 10%+ holder, and must be filed within two business days of the transaction — so this is close to real time, unlike the 45-day-lagged 13F institutional data.
Transaction codes matter more than the raw buy/sell count. Code P is an open-market purchase — an insider choosing to buy with their own money, which is the signal most research treats as informative. Code S is a sale, but sales are frequently pre-scheduled under a 10b5-1 plan or cover tax withholding on vesting equity, so a run of sales often says nothing directional. Codes A and M are grants and option exercises rather than open-market decisions.
Full filing history and per-insider positions are on the UPLD quote page; the site-wide leaderboard is on the insider transactions hub.
Market data may be delayed, incomplete, or inaccurate. Not a recommendation to buy, sell, or hold any security. Verify quotes with your broker before trading. See Terms §17.