Upland Software, Inc. — Insider Transactions
Form 4 filings by directors, officers, and 10%+ shareholders
SEC rules require corporate insiders — including directors, executive officers, and any shareholder owning more than 10% of a company's shares — to report changes in their ownership within two business days of a transaction. These disclosures are filed as Form 4. Open-market purchases (code P) are generally considered the most meaningful signal, as insiders are spending their own money.
| Insider | Title | Type | Shares | Price | Value | Owns After | Date |
|---|---|---|---|---|---|---|---|
| Doman Dan | Chief Operating & Product Ofcr | Tax Withholding | 24,595 | $1.49 | $36,647 | 707,257 | Dec 16, 2025 |
| MCDONALD JOHN T | CEO | Tax Withholding | 19,677 | $1.49 | $29,319 | 2,409,492 | Dec 16, 2025 |
| Hill Michael Douglass | CFO, Treasurer & Secretary | Tax Withholding | 8,856 | $1.49 | $13,195 | 331,222 | Dec 16, 2025 |
| Chung David H S | — | Award / Grant | 25,000 | — | — | 124,484 | Oct 27, 2025 |
| COURTER STEPHEN E | — | Award / Grant | 25,000 | — | — | 124,232 | Oct 27, 2025 |
| Mattox Timothy | — | Award / Grant | 25,000 | — | — | 419,008 | Oct 27, 2025 |
| MAY DAVID | — | Award / Grant | 25,000 | — | — | 191,437 | Oct 27, 2025 |
| Walsh Teresa Miles | — | Award / Grant | 25,000 | — | — | 144,490 | Oct 27, 2025 |
| MCDONALD JOHN T | CEO | Tax Withholding | 22,956 | $2.48 | $56,931 | 2,429,169 | Sep 16, 2025 |
| Hill Michael Douglass | CFO, Treasurer & Secretary | Tax Withholding | 11,152 | $2.48 | $27,657 | 340,078 | Sep 16, 2025 |
| Doman Dan | Chief Operating & Product Ofcr | Tax Withholding | 26,236 | $2.48 | $65,065 | 731,852 | Sep 16, 2025 |
| MCDONALD JOHN T | CEO | Sale | 14,438 | $2.36 | $34,074 | 2,452,125 | Sep 11, 2025 |
| Cummings Karen | President and COO | Tax Withholding | 40,993 | $1.95 | $79,936 | 306,432 | Jun 30, 2025 |
| Smith Matthew Harnden | General Counsel and Secretary | Tax Withholding | 3,596 | $1.84 | $6,617 | 131,908 | Jun 16, 2025 |
| MCDONALD JOHN T | CEO | Tax Withholding | 22,957 | $1.84 | $42,241 | 2,466,563 | Jun 16, 2025 |
| Hill Michael Douglass | CFO & Treasurer | Tax Withholding | 11,152 | $1.84 | $20,520 | 351,230 | Jun 16, 2025 |
| Cummings Karen | President and COO | Tax Withholding | 11,479 | $1.84 | $21,121 | 347,425 | Jun 16, 2025 |
| Doman Dan | Chief Product Officer | Tax Withholding | 14,758 | $1.84 | $27,155 | 758,088 | Jun 13, 2025 |
| Mattox Timothy | — | Sale | 20,000 | $3.19 | $63,800 | 394,008 | Mar 17, 2025 |
| Smith Matthew Harnden | General Counsel and Secretary | Tax Withholding | 4,135 | $3.10 | $12,819 | 135,504 | Mar 16, 2025 |
| MCDONALD JOHN T | CEO | Tax Withholding | 24,273 | $3.10 | $75,246 | 2,489,520 | Mar 16, 2025 |
| Hill Michael Douglass | CFO & Treasurer | Tax Withholding | 12,653 | $3.10 | $39,224 | 362,382 | Mar 16, 2025 |
| Doman Dan | Chief Product Officer | Tax Withholding | 16,414 | $3.10 | $50,883 | 422,846 | Mar 16, 2025 |
| Cummings Karen | President and COO | Tax Withholding | 8,648 | $3.10 | $26,809 | 358,904 | Mar 16, 2025 |
| Smith Matthew Harnden | General Counsel and Secretary | Award / Grant | 50,000 | — | — | 139,639 | Jan 28, 2025 |
| MCDONALD JOHN T | CEO | Award / Grant | 250,000 | — | — | 2,513,793 | Jan 28, 2025 |
| Hill Michael Douglass | CFO & Treasurer | Award / Grant | 70,000 | — | — | 375,035 | Jan 28, 2025 |
| Doman Dan | Chief Product Officer | Award / Grant | 150,000 | — | — | 439,260 | Jan 28, 2025 |
| Mattox Timothy | — | Sale | 2,768 | $4.56 | $12,622 | 414,008 | Dec 17, 2024 |
| Smith Matthew Harnden | General Counsel and Secretary | Tax Withholding | 6,197 | $4.51 | $27,948 | 89,639 | Dec 16, 2024 |
| MCDONALD JOHN T | CEO | Tax Withholding | 17,833 | $4.51 | $80,427 | 2,263,793 | Dec 16, 2024 |
| Hill Michael Douglass | CFO & Treasurer | Tax Withholding | 11,070 | $4.51 | $49,926 | 305,035 | Dec 16, 2024 |
| Doman Dan | Chief Product Officer | Tax Withholding | 11,643 | $4.51 | $52,510 | 289,260 | Dec 16, 2024 |
| Cummings Karen | President and COO | Tax Withholding | 7,812 | $4.51 | $35,232 | 367,552 | Dec 16, 2024 |
| MCDONALD JOHN T | CEO | Option Exercise | 187,500 | — | — | 2,355,407 | Dec 6, 2024 |
| MCDONALD JOHN T | CEO | Option Exercise | 156,250 | — | — | 1,983,001 | Dec 4, 2024 |
| Mattox Timothy | — | Sale | 18,000 | $2.50 | $45,000 | 416,776 | Nov 13, 2024 |
| Chung David H S | — | Award / Grant | 25,000 | — | — | 99,484 | Nov 4, 2024 |
| COURTER STEPHEN E | — | Award / Grant | 25,000 | — | — | 99,232 | Nov 4, 2024 |
| Mattox Timothy | — | Award / Grant | 25,000 | — | — | 436,776 | Nov 4, 2024 |
| Walsh Teresa Miles | — | Award / Grant | 25,000 | — | — | 119,490 | Nov 4, 2024 |
| MAY DAVID | — | Award / Grant | 25,000 | — | — | 166,437 | Nov 4, 2024 |
| Smith Matthew Harnden | General Counsel and Secretary | Tax Withholding | 1,240 | $2.24 | $2,778 | 95,836 | Sep 16, 2024 |
| MCDONALD JOHN T | CEO | Tax Withholding | 17,833 | $2.24 | $39,946 | 1,826,751 | Sep 16, 2024 |
| Cummings Karen | President and COO | Tax Withholding | 7,815 | $2.24 | $17,506 | 375,364 | Sep 16, 2024 |
| Doman Dan | Chief Product Officer | Tax Withholding | 11,643 | $2.24 | $26,080 | 300,903 | Sep 16, 2024 |
| Hill Michael Douglass | CFO & Treasurer | Tax Withholding | 11,070 | $2.24 | $24,797 | 316,105 | Sep 16, 2024 |
| MCDONALD JOHN T | CEO | Purchase | 66,365 | $1.96 | $130,075 | 363,738 | Aug 8, 2024 |
| Smith Matthew Harnden | General Counsel and Secretary | Tax Withholding | 1,460 | $2.63 | $3,840 | 97,076 | Jun 16, 2024 |
| Cummings Karen | President and COO | Tax Withholding | 7,815 | $2.63 | $20,553 | 383,179 | Jun 16, 2024 |