The public view is the crawlable proof. The same sourced dataset is available through REST and MCP for agents, research scripts, and back-office tools.
| Date | Insider | Role | Action | Shares | Price | Value |
|---|---|---|---|---|---|---|
| Aug 17, 2026 | Simon Jennifer L. | Chief Financial Officer | Grant(A) | 7K | — | $0 |
| Aug 17, 2026 | Simon Jennifer L. | Chief Financial Officer | Grant(A) | 30K | — | $0 |
| Aug 7, 2026 | Mattox Timothy | Director | Sell(S) | 847 | $4.28 | $4K |
| Aug 6, 2026 | Mattox Timothy | Director | Sell(S) | 1K | $4.27 | $4K |
| Aug 5, 2026 | Mattox Timothy | Director | Sell(S) | 1K | $4.53 | $5K |
| Aug 4, 2026 | Mattox Timothy | Director | Sell(S) | 1K | $4.33 | $4K |
| Aug 3, 2026 | Mattox Timothy | Director | Sell(S) | 1K | $4.45 | $4K |
| Jul 31, 2026 | Mattox Timothy | Director | Sell(S) | 1K | $4.48 | $4K |
| Jun 16, 2026 | Nathaniel Sean | CEO and President | Tax withholding(F) | 19K | $0.61 | $11K |
| Jun 16, 2026 | Doman Dan | Chief Operating & Product Ofcr | Tax withholding(F) | 30K | $0.61 | $18K |
| Jun 16, 2026 | Hill Michael Douglass | CFO, Treasurer & Secretary | Tax withholding(F) | 9K | $0.61 | $5K |
| Jun 4, 2026 | Nathaniel Sean | CEO and President | Grant(A) | 500K | — | $0 |
| Jun 4, 2026 | Nathaniel Sean | CEO and President | Grant(A) | 133K | — | $0 |
| Apr 30, 2026 | McDonald John T | Director | Grant(A) | 250K | — | $0 |
| Apr 30, 2026 | McDonald John T | Director | Disposed to issuer(D) | 250K | — | $0 |
| Mar 16, 2026 | McDonald John T | CEO, Director | Tax withholding(F) | 19K | $0.54 | $10K |
| Mar 16, 2026 | Hill Michael Douglass | CFO, Treasurer & Secretary | Tax withholding(F) | 9K | $0.54 | $5K |
| Mar 16, 2026 | Doman Dan | Chief Operating & Product Ofcr | Tax withholding(F) | 33K | $0.54 | $18K |
| Feb 27, 2026 | Doman Dan | Chief Operating & Product Ofcr | Grant(A) | 100K | — | $0 |
| Feb 23, 2026 | Hill Michael Douglass | CFO, Treasurer & Secretary | Grant(A) | 70K | — | $0 |
| Feb 23, 2026 | Doman Dan | Chief Operating & Product Ofcr | Grant(A) | 150K | — | $0 |
| Dec 16, 2025 | McDonald John T | CEO, Director | Tax withholding(F) | 20K | $1.49 | $29K |
| Dec 16, 2025 | Hill Michael Douglass | CFO, Treasurer & Secretary | Tax withholding(F) | 9K | $1.49 | $13K |
| Dec 16, 2025 | Doman Dan | Chief Operating & Product Ofcr | Tax withholding(F) | 25K | $1.49 | $37K |
| Oct 27, 2025 | Courter Stephen E | Director | Grant(A) | 25K | — | $0 |
| Oct 27, 2025 | May David | Director | Grant(A) | 25K | — | $0 |
| Oct 27, 2025 | Mattox Timothy | Director | Grant(A) | 25K | — | $0 |
| Oct 27, 2025 | Chung David H S | Director | Grant(A) | 25K | — | $0 |
| Oct 27, 2025 | Walsh Teresa Miles | Director | Grant(A) | 25K | — | $0 |
| Sep 16, 2025 | McDonald John T | CEO, Director | Tax withholding(F) | 23K | $2.48 | $57K |
| Sep 16, 2025 | Hill Michael Douglass | CFO, Treasurer & Secretary | Tax withholding(F) | 11K | $2.48 | $28K |
| Sep 16, 2025 | Doman Dan | Chief Operating & Product Ofcr | Tax withholding(F) | 26K | $2.48 | $65K |
| Sep 11, 2025 | McDonald John T | CEO, Director | Sell(S) | 14K | $2.36 | $34K |
| Jun 30, 2025 | Cummings Karen | President and COO | Tax withholding(F) | 41K | $1.95 | $80K |
| Jun 16, 2025 | Cummings Karen | President and COO | Tax withholding(F) | 11K | $1.84 | $21K |
| Jun 16, 2025 | Doman Dan | Chief Product Officer | Tax withholding(F) | 15K | $1.84 | $27K |
| Jun 16, 2025 | Hill Michael Douglass | CFO & Treasurer | Tax withholding(F) | 11K | $1.84 | $21K |
| Jun 16, 2025 | McDonald John T | CEO, Director | Tax withholding(F) | 23K | $1.84 | $42K |
| Jun 16, 2025 | Smith Matthew Harnden | General Counsel and Secretary | Tax withholding(F) | 4K | $1.84 | $7K |
| Jun 13, 2025 | Doman Dan | Chief Product Officer | Grant(A) | 350K | — | $0 |
| Mar 17, 2025 | Mattox Timothy | Director | Sell(S) | 20K | $3.19 | $64K |
| Mar 16, 2025 | Cummings Karen | President and COO | Tax withholding(F) | 9K | $3.10 | $27K |
| Mar 16, 2025 | Doman Dan | Chief Product Officer | Tax withholding(F) | 16K | $3.10 | $51K |
| Mar 16, 2025 | Hill Michael Douglass | CFO & Treasurer | Tax withholding(F) | 13K | $3.10 | $39K |
| Mar 16, 2025 | McDonald John T | CEO, Director | Tax withholding(F) | 24K | $3.10 | $75K |
| Mar 16, 2025 | Smith Matthew Harnden | General Counsel and Secretary | Tax withholding(F) | 4K | $3.10 | $13K |
| Jan 28, 2025 | Doman Dan | Chief Product Officer | Grant(A) | 150K | — | $0 |
| Jan 28, 2025 | Hill Michael Douglass | CFO & Treasurer | Grant(A) | 70K | — | $0 |
| Jan 28, 2025 | McDonald John T | CEO, Director | Grant(A) | 250K | — | $0 |
| Jan 28, 2025 | McDonald John T | CEO, Director | Grant(A) | 250K | — | $0 |
| Jan 28, 2025 | Smith Matthew Harnden | General Counsel and Secretary | Grant(A) | 50K | — | $0 |
| Dec 17, 2024 | Mattox Timothy | Director | Sell(S) | 3K | $4.56 | $13K |
| Dec 16, 2024 | Cummings Karen | President and COO | Tax withholding(F) | 8K | $4.51 | $35K |
| Dec 16, 2024 | Doman Dan | Chief Product Officer | Tax withholding(F) | 12K | $4.51 | $53K |
| Dec 16, 2024 | Hill Michael Douglass | CFO & Treasurer | Tax withholding(F) | 11K | $4.51 | $50K |
| Dec 16, 2024 | McDonald John T | CEO, Director | Tax withholding(F) | 18K | $4.51 | $80K |
| Dec 16, 2024 | Smith Matthew Harnden | General Counsel and Secretary | Tax withholding(F) | 6K | $4.51 | $28K |
| Dec 10, 2024 | McDonald John T | CEO, Director | Tax withholding(F) | 74K | $5.31 | $392K |
| Dec 10, 2024 | McDonald John T | CEO, Director | Option exercise(M) | 188K | — | $0 |
| Dec 10, 2024 | McDonald John T | CEO, Director | Option exercise(M) | 188K | — | $0 |
| Dec 9, 2024 | McDonald John T | CEO, Director | Option exercise(M) | 125K | — | $0 |
| Dec 9, 2024 | McDonald John T | CEO, Director | Tax withholding(F) | 49K | $4.89 | $241K |
| Dec 9, 2024 | McDonald John T | CEO, Director | Option exercise(M) | 125K | — | $0 |
| Dec 6, 2024 | McDonald John T | CEO, Director | Option exercise(M) | 188K | — | $0 |
| Dec 6, 2024 | McDonald John T | CEO, Director | Tax withholding(F) | 74K | $4.45 | $328K |
| Dec 6, 2024 | McDonald John T | CEO, Director | Option exercise(M) | 188K | — | $0 |
| Dec 5, 2024 | McDonald John T | CEO, Director | Option exercise(M) | 63K | — | $0 |
| Dec 5, 2024 | McDonald John T | CEO, Director | Tax withholding(F) | 25K | $4.32 | $106K |
| Dec 5, 2024 | McDonald John T | CEO, Director | Option exercise(M) | 63K | — | $0 |
| Dec 4, 2024 | McDonald John T | CEO, Director | Tax withholding(F) | 12K | $4.00 | $49K |
| Dec 4, 2024 | McDonald John T | CEO, Director | Option exercise(M) | 31K | — | $0 |
| Dec 4, 2024 | McDonald John T | CEO, Director | Option exercise(M) | 31K | — | $0 |
| Dec 3, 2024 | McDonald John T | CEO, Director | Tax withholding(F) | 61K | $4.37 | $269K |
| Dec 3, 2024 | McDonald John T | CEO, Director | Option exercise(M) | 156K | — | $0 |
| Dec 3, 2024 | McDonald John T | CEO, Director | Option exercise(M) | 156K | — | $0 |
| Nov 14, 2024 | Mattox Timothy | Director | Sell(S) | 18K | $2.50 | $45K |
| Nov 13, 2024 | Mattox Timothy | Director | Sell(S) | 2K | $2.64 | $5K |
| Nov 4, 2024 | May David | Director | Grant(A) | 25K | — | $0 |
| Nov 4, 2024 | Mattox Timothy | Director | Grant(A) | 25K | — | $0 |
| Nov 4, 2024 | Courter Stephen E | Director | Grant(A) | 25K | — | $0 |
| Nov 4, 2024 | Chung David H S | Director | Grant(A) | 25K | — | $0 |
| Nov 4, 2024 | Walsh Teresa Miles | Director | Grant(A) | 25K | — | $0 |
| Sep 16, 2024 | Hill Michael Douglass | CFO & Treasurer | Tax withholding(F) | 11K | $2.24 | $25K |
| Sep 16, 2024 | Doman Dan | Chief Product Officer | Tax withholding(F) | 12K | $2.24 | $26K |
| Sep 16, 2024 | Cummings Karen | President and COO | Tax withholding(F) | 8K | $2.24 | $18K |
| Sep 16, 2024 | McDonald John T | CEO, Director | Tax withholding(F) | 18K | $2.24 | $40K |
| Sep 16, 2024 | Smith Matthew Harnden | General Counsel and Secretary | Tax withholding(F) | 1K | $2.24 | $3K |
| Aug 9, 2024 | McDonald John T | CEO, Director | Buy(P) | 66K | $1.96 | $130K |
| Aug 8, 2024 | McDonald John T | CEO, Director | Buy(P) | 34K | $1.98 | $67K |
| Jun 16, 2024 | McDonald John T | CEO, Director | Tax withholding(F) | 18K | $2.63 | $47K |
| Jun 16, 2024 | Hill Michael Douglass | CFO & Treasurer | Tax withholding(F) | 11K | $2.63 | $29K |
| Jun 16, 2024 | Cummings Karen | President and COO | Tax withholding(F) | 8K | $2.63 | $21K |
| Jun 16, 2024 | Smith Matthew Harnden | General Counsel and Secretary | Tax withholding(F) | 1K | $2.63 | $4K |
| Jun 16, 2024 | Doman Dan | Chief Product Officer | Tax withholding(F) | 13K | $2.63 | $35K |
| Jun 5, 2024 | McDonald John T | CEO, Director | Grant(A) | 500K | — | $0 |
| Mar 16, 2024 | McDonald John T | CEO, Director | Tax withholding(F) | 19K | $4.21 | $81K |
| Mar 16, 2024 | Hill Michael Douglass | CFO & Treasurer | Tax withholding(F) | 13K | $4.21 | $53K |
| Mar 16, 2024 | Cummings Karen | President and COO | Tax withholding(F) | 10K | $4.21 | $40K |
| Mar 16, 2024 | Smith Matthew Harnden | General Counsel and Secretary | Tax withholding(F) | 1K | $4.21 | $6K |
| Mar 16, 2024 | Doman Dan | Chief Product Officer | Tax withholding(F) | 15K | $4.21 | $64K |
Insider transactions sourced from SEC EDGAR Form 4 filings, normalized within minutes of acceptance. "Buy"/"Sell" mark open-market transactions (codes P/S), the tradeable signal. Awards, option exercises and tax-withholding are shown with their raw code. All data is public domain.
Issuer: Upland Software, Inc., SEC CIK 0001505155. The symbol on a Form 4 is typed by the filer, so this page follows the issuer with the newest filing under UPLD and shows every filing by that issuer.
Coverage: Form 4 filings indexed 2006-01-02 → 2026-09-14. Earlier history is backfilling; this window widens as it deepens.
Programmatic access via the Arkolith API & MCP server (insider.transactions, insider.company).
Connected pages for UPLD