12 insiders reported 43 Form 4 transactions for Upland Software, Inc. (UPLD) over the past 18 months (most recent 2026-08-18). Recent activity: Simon Jennifer L. (Chief Financial Officer) Buy 30,000 shares, Mattox Timothy (Director) Sell 847 shares, Mattox Timothy (Director) Sell 1,000 shares, Mattox Timothy (Director) Sell 1,000 shares, Mattox Timothy (Director) Sell 1,000 shares. Source: SEC Form 4.
| Date | Insider | Title | Type | Shares | Value |
|---|---|---|---|---|---|
| 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 | $5,416 |
| 2026-06-16 | Nathaniel Sean | CEO and President | Sell | 18,605 | $11,282 |
| 2026-06-16 | Doman Dan | Chief Operating & Product Ofcr | Sell | 29,515 | $17,898 |
| 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 |
| 2025-10-29 | Mattox Timothy | Director | Buy | 25,000 | $0 |
| 2025-10-29 | MAY DAVID | Director | Buy | 25,000 | $0 |
| 2025-10-29 | COURTER STEPHEN E | Director | Buy | 25,000 | $0 |
Source: SEC Form 4 filings · as of 2026-08-18