12 insiders reported 40 Form 4 transactions for Upland Software, Inc. (UPLD) over the past 18 months (most recent 2026-09-21). Recent activity: Nathaniel Sean (CEO and President) Sell 1,640 shares, Doman Dan (Chief Operating & Product Ofcr) Sell 2,952 shares, Simon Jennifer L. (Chief Financial Officer) Sell 1,117 shares, Simon Jennifer L. (Chief Financial Officer) Buy 30,000 shares, Mattox Timothy (Director) Sell 847 shares. Source: SEC Form 4.
| Date | Insider | Title | Type | Shares | Value |
|---|---|---|---|---|---|
| 2026-09-21 | Nathaniel Sean | CEO and President | Sell | 1,640 | $6,470 |
| 2026-09-21 | Doman Dan | Chief Operating & Product Ofcr | Sell | 2,952 | $11,646 |
| 2026-09-21 | Simon Jennifer L. | Chief Financial Officer | Sell | 1,117 | $4,407 |
| 2026-08-18 | Simon Jennifer L. | Chief Financial Officer | Buy | 30,000 | $0 |
| 2026-08-11 | Mattox Timothy | Director | Sell | 847 | $3,627 |
| 2026-08-10 | Mattox Timothy | Director | Sell | 1,000 | $4,270 |
| 2026-08-06 | Mattox Timothy | Director | Sell | 1,000 | $4,330 |
| 2026-08-06 | Mattox Timothy | Director | Sell | 1,000 | $4,530 |
| 2026-08-04 | Mattox Timothy | Director | Sell | 1,000 | $4,480 |
| 2026-08-04 | Mattox Timothy | Director | Sell | 1,000 | $4,450 |
| 2026-06-16 | Hill Michael Douglass | CFO, Treasurer & Secretary | Sell | 8,931 | $5,448 |
| 2026-06-16 | Doman Dan | Chief Operating & Product Ofcr | Sell | 29,515 | $18,004 |
| 2026-06-16 | Nathaniel Sean | CEO and President | Sell | 18,605 | $11,349 |
| 2026-06-08 | Nathaniel Sean | CEO and President | Buy | 500,000 | $0 |
| 2026-05-04 | MCDONALD JOHN T | Director | Buy | 250,000 | $0 |
| 2026-03-17 | Doman Dan | Chief Operating & Product Ofcr | Sell | 33,491 | $18,085 |
| 2026-03-17 | Hill Michael Douglass | CFO, Treasurer & Secretary | Sell | 8,931 | $4,823 |
| 2026-03-17 | MCDONALD JOHN T | CEO | Sell | 18,605 | $10,047 |
| 2026-03-03 | Doman Dan | Chief Operating & Product Ofcr | Buy | 100,000 | $0 |
| 2026-02-25 | Doman Dan | Chief Operating & Product Ofcr | Buy | 150,000 | $0 |
| 2026-02-25 | Hill Michael Douglass | CFO, Treasurer & Secretary | Buy | 70,000 | $0 |
| 2025-12-17 | Hill Michael Douglass | CFO, Treasurer & Secretary | Sell | 8,856 | $13,195 |
| 2025-12-17 | Doman Dan | Chief Operating & Product Ofcr | Sell | 24,595 | $36,647 |
| 2025-12-17 | MCDONALD JOHN T | CEO | Sell | 19,677 | $29,319 |
| 2025-10-29 | Walsh Teresa Miles | Director | Buy | 25,000 | $0 |
Source: SEC Form 4 filings · as of 2026-09-21