GWRE · Guidewire Software, Inc.
Trades by corporate insiders — officers, directors and holders of more than 10% of the shares — disclosed to the SEC on Forms 4 and 5. Form 3 supplies initial ownership rather than a trade; Form 4 must be filed within two business days of the trade.
Insider Sentiment Score
Peer-relative 0–100 rank of how aggressively insiders accumulated over the trailing 90 days. See the full ranking.
| Date | Insider | Role | Type | Security | Shares |
|---|---|---|---|---|---|
| 2026-08-31 | Rosenbaum Michael George |
Director, Chief Executive Officer |
Sell↓
Filing footnotes — Common Stock (Direct)
Automatic sale pursuant to a 10b5-1 Trading Plan adopted by the Reporting Person on October 14, 2025. |
Common Stock
|
1,200 |
| 2026-08-27 | Peterson David Franklin |
Chief Accounting Officer |
Sell↓
Filing footnotes — Common Stock (Direct)
Automatic sale pursuant to a 10b5-1 Trading Plan adopted by the Reporting Person on October 10, 2025. |
Common Stock
|
2,500 |
| 2026-08-25 | Mullen John P |
President |
Sell↓
Filing footnotes — Common Stock (Direct)
Automatic sale pursuant to a 10b5-1 Trading Plan adopted by the Reporting Person on October 14, 2025, as amended January 13, 2026. |
Common Stock
|
1,800 |
| 2026-08-24 | Rosenbaum Michael George |
Director, Chief Executive Officer |
Sell↓
Filing footnotes — Common Stock (Direct)
Automatic sale pursuant to a 10b5-1 Trading Plan adopted by the Reporting Person on October 14, 2025. |
Common Stock
|
1,200 |
| 2026-08-19 | Mullen John P |
President |
Sell↓
Filing footnotes — Common Stock (Direct)
Automatic sale pursuant to a 10b5-1 Trading Plan adopted by the Reporting Person on October 14, 2025, as amended January 13, 2026. |
Common Stock
|
16,200 |
| 2026-08-17 | Rosenbaum Michael George |
Director, Chief Executive Officer |
Sell↓
Filing footnotes — Common Stock (Direct)
Automatic sale pursuant to a 10b5-1 Trading Plan adopted by the Reporting Person on October 14, 2025. |
Common Stock
|
1,200 |
| 2026-08-12 | Vollert Karl Alexander |
Director |
Award↑
Filing footnotes — Common Stock (Direct)
These restricted stock units were granted on August 12, 2026, and are scheduled to become 100% vested after the earlier of one year from the grant date or Issuer's next annual meeting of stockholders. |
Common Stock
|
578 |
| 2026-08-10 | Rosenbaum Michael George |
Director, Chief Executive Officer |
Sell↓
Filing footnotes — Common Stock (Direct)
Automatic sale pursuant to a 10b5-1 Trading Plan adopted by the Reporting Person on October 14, 2025. |
Common Stock
|
1,200 |
| 2026-08-03 | Rosenbaum Michael George |
Director, Chief Executive Officer |
Sell↓
Filing footnotes — Common Stock (Direct)
Automatic sale pursuant to a 10b5-1 Trading Plan adopted by the Reporting Person on October 14, 2025. |
Common Stock
|
1,200 |
| 2026-07-27 | Rosenbaum Michael George |
Director, Chief Executive Officer |
Sell↓
Filing footnotes — Common Stock (Direct)
Automatic sale pursuant to a 10b5-1 Trading Plan adopted by the Reporting Person on October 14, 2025. |
Common Stock
|
1,200 |
| 2026-07-20 | Rosenbaum Michael George |
Director, Chief Executive Officer |
Sell↓
Filing footnotes — Common Stock (Direct)
Automatic sale pursuant to a 10b5-1 Trading Plan adopted by the Reporting Person on October 14, 2025. |
Common Stock
|
1,200 |
| 2026-07-13 | Rosenbaum Michael George |
Director, Chief Executive Officer |
Sell↓
Filing footnotes — Common Stock (Direct)
Automatic sale pursuant to a 10b5-1 Trading Plan adopted by the Reporting Person on October 14, 2025. |
Common Stock
|
1,200 |
| 2026-07-09 | King James Winston |
Chief Admin Officer, Gen Couns |
Sell↓
Filing footnotes — Common Stock (Direct)
Automatic sale pursuant to a 10b5-1 Trading Plan adopted by the Reporting Person on October 14, 2025, as amended on April 9, 2026. |
Common Stock
|
1,684 |
| 2026-07-06 | Rosenbaum Michael George |
Director, Chief Executive Officer |
Sell↓
Filing footnotes — Common Stock (Direct)
Automatic sale pursuant to a 10b5-1 Trading Plan adopted by the Reporting Person on October 14, 2025. |
Common Stock
|
1,200 |
| 2026-06-29 | Rosenbaum Michael George |
Director, Chief Executive Officer |
Sell↓
Filing footnotes — Common Stock (Direct)
Automatic sale pursuant to a 10b5-1 Trading Plan adopted by the Reporting Person on October 14, 2025. |
Common Stock
|
1,200 |
| 2026-06-22 | Cooper Jeffrey Elliott |
Chief Financial Officer |
Sell↓
Filing footnotes — Common Stock (Direct)
Automatic sale pursuant to a 10b5-1 Trading Plan adopted by the Reporting Person on March 20, 2026. |
Common Stock
|
1,348 |
| 2026-06-22 | Rosenbaum Michael George |
Director, Chief Executive Officer |
Sell↓
Filing footnotes — Common Stock (Direct)
Automatic sale pursuant to a 10b5-1 Trading Plan adopted by the Reporting Person on October 14, 2025. |
Common Stock
|
1,200 |
| 2026-06-16 | King James Winston |
Chief Admin Officer, Gen Couns |
Sell↓
Filing footnotes — Common Stock (Direct)
Shares sold by Issuer to cover taxes associated with settlement of Restricted Stock Units. |
Common Stock
|
999 |
| 2026-06-16 | Cooper Jeffrey Elliott |
Chief Financial Officer |
Sell↓
Filing footnotes — Common Stock (Direct)
Shares sold by Issuer to cover taxes associated with settlement of Restricted Stock Units. |
Common Stock
|
2,594 |
| 2026-06-16 | Mullen John P |
President |
Sell↓
Filing footnotes — Common Stock (Direct)
Shares sold by Issuer to cover taxes associated with settlement of Restricted Stock Units. |
Common Stock
|
4,292 |
| 2026-06-16 | Peterson David Franklin |
Chief Accounting Officer |
Sell↓
Filing footnotes — Common Stock (Direct)
Shares sold by Issuer to cover taxes associated with settlement of Restricted Stock Units. |
Common Stock
|
246 |
| 2026-06-16 | Rosenbaum Michael George |
Director, Chief Executive Officer |
Sell↓
Filing footnotes — Common Stock (Direct)
Shares sold by Issuer to cover taxes associated with settlement of Restricted Stock Units. |
Common Stock
|
5,830 |
| 2026-06-15 | Rosenbaum Michael George |
Director, Chief Executive Officer |
Sell↓
Filing footnotes — Common Stock (Direct)
Automatic sale pursuant to a 10b5-1 Trading Plan adopted by the Reporting Person on October 14, 2025. |
Common Stock
|
1,200 |
| 2026-06-08 | Rosenbaum Michael George |
Director, Chief Executive Officer |
Sell↓
Filing footnotes — Common Stock (Direct)
Automatic sale pursuant to a 10b5-1 Trading Plan adopted by the Reporting Person on October 14, 2025. |
Common Stock
|
1,200 |
| 2026-06-01 | Rosenbaum Michael George |
Director, Chief Executive Officer |
Sell↓
Filing footnotes — Common Stock (Direct)
Automatic sale pursuant to a 10b5-1 Trading Plan adopted by the Reporting Person on October 14, 2025. |
Common Stock
|
1,200 |
| 2026-05-26 | Rosenbaum Michael George |
Director, Chief Executive Officer |
Sell↓
Filing footnotes — Common Stock (Direct)
Automatic sale pursuant to a 10b5-1 Trading Plan adopted by the Reporting Person on October 14, 2025. |
Common Stock
|
1,200 |
| 2026-05-18 | Rosenbaum Michael George |
Director, Chief Executive Officer |
Sell↓
Filing footnotes — Common Stock (Direct)
Automatic sale pursuant to a 10b5-1 Trading Plan adopted by the Reporting Person on October 14, 2025. |
Common Stock
|
1,200 |
| 2026-05-11 | Rosenbaum Michael George |
Director, Chief Executive Officer |
Sell↓
Filing footnotes — Common Stock (Direct)
Automatic sale pursuant to a 10b5-1 Trading Plan adopted by the Reporting Person on October 14, 2025. |
Common Stock
|
1,200 |
| 2026-05-04 | Rosenbaum Michael George |
Director, Chief Executive Officer |
Sell↓
Filing footnotes — Common Stock (Direct)
Automatic sale pursuant to a 10b5-1 Trading Plan adopted by the Reporting Person on October 14, 2025. |
Common Stock
|
1,200 |
| 2026-04-27 | Rosenbaum Michael George |
Director, Chief Executive Officer |
Sell↓
Filing footnotes — Common Stock (Direct)
Automatic sale pursuant to a 10b5-1 Trading Plan adopted by the Reporting Person on October 14, 2025. |
Common Stock
|
1,200 |
| 2026-04-20 | Rosenbaum Michael George |
Director, Chief Executive Officer |
Sell↓
Filing footnotes — Common Stock (Direct)
Automatic sale pursuant to a 10b5-1 Trading Plan adopted by the Reporting Person on October 14, 2025. |
Common Stock
|
1,200 |
| 2026-04-13 | Rosenbaum Michael George |
Director, Chief Executive Officer |
Sell↓
Filing footnotes — Common Stock (Direct)
Automatic sale pursuant to a 10b5-1 Trading Plan adopted by the Reporting Person on October 14, 2025. |
Common Stock
|
1,200 |
| 2026-04-06 | Rosenbaum Michael George |
Director, Chief Executive Officer |
Sell↓
Filing footnotes — Common Stock (Direct)
Automatic sale pursuant to a 10b5-1 Trading Plan adopted by the Reporting Person on October 14, 2025. |
Common Stock
|
1,200 |
| 2026-03-30 | Rosenbaum Michael George |
Director, Chief Executive Officer |
Sell↓
Filing footnotes — Common Stock (Direct)
Automatic sale pursuant to a 10b5-1 Trading Plan adopted by the Reporting Person on October 14, 2025. |
Common Stock
|
1,200 |
| 2026-03-23 | Rosenbaum Michael George |
Director, Chief Executive Officer |
Sell↓
Filing footnotes — Common Stock (Direct)
Automatic sale pursuant to a 10b5-1 Trading Plan adopted by the Reporting Person on October 14, 2025. |
Common Stock
|
1,200 |
| 2026-03-17 | Mullen John P |
President |
Sell↓
Filing footnotes — Common Stock (Direct)
Shares sold by Issuer to cover taxes associated with settlement of Restricted Stock Units. |
Common Stock
|
6,576 |
| 2026-03-17 | Peterson David Franklin |
Chief Accounting Officer |
Sell↓
Filing footnotes — Common Stock (Direct)
Shares sold by Issuer to cover taxes associated with settlement of Restricted Stock Units. |
Common Stock
|
273 |
| 2026-03-17 | Cooper Jeffrey Elliott |
Chief Financial Officer |
Sell↓
Filing footnotes — Common Stock (Direct)
Shares sold by Issuer to cover taxes associated with settlement of Restricted Stock Units. |
Common Stock
|
1,935 |
| 2026-03-17 | King James Winston |
Chief Admin Officer, Gen Couns |
Sell↓
Filing footnotes — Common Stock (Direct)
Shares sold by Issuer to cover taxes associated with settlement of Restricted Stock Units. |
Common Stock
|
1,001 |
| 2026-03-17 | Rosenbaum Michael George |
Director, Chief Executive Officer |
Sell↓
Filing footnotes — Common Stock (Direct)
Shares sold by Issuer to cover taxes associated with settlement of Restricted Stock Units. |
Common Stock
|
4,737 |
| 2026-03-16 | Rosenbaum Michael George |
Director, Chief Executive Officer |
Sell↓
Filing footnotes — Common Stock (Direct)
Automatic sale pursuant to a 10b5-1 Trading Plan adopted by the Reporting Person on October 14, 2025. |
Common Stock
|
1,200 |
| 2026-03-13 | Cooper Jeffrey Elliott |
Chief Financial Officer |
Sell↓
Filing footnotes — Common Stock (Direct)
This transaction was not made under a Rule 10b5-1 trading plan. The Reporting Person terminated his October 14, 2025, Rule 10b5-1 trading plan on February 5, 2026. This trade was made during the Issuer's open trading window in compliance with Issuer's Insider Trading Policy. |
Common Stock
|
4,757 |
| 2026-03-09 | Rosenbaum Michael George |
Director, Chief Executive Officer |
Sell↓
Filing footnotes — Common Stock (Direct)
Automatic sale pursuant to a 10b5-1 Trading Plan adopted by the Reporting Person on October 14, 2025. |
Common Stock
|
1,200 |
| 2026-03-02 | Rosenbaum Michael George |
Director, Chief Executive Officer |
Sell↓
Filing footnotes — Common Stock (Direct)
Automatic sale pursuant to a 10b5-1 Trading Plan adopted by the Reporting Person on October 14, 2025. |
Common Stock
|
1,200 |
| 2026-02-23 | Rosenbaum Michael George |
Director, Chief Executive Officer |
Sell↓
Filing footnotes — Common Stock (Direct)
Automatic sale pursuant to a 10b5-1 Trading Plan adopted by the Reporting Person on October 14, 2025. |
Common Stock
|
1,200 |
| 2026-02-17 | Rosenbaum Michael George |
Director, Chief Executive Officer |
Sell↓
Filing footnotes — Common Stock (Direct)
Automatic sale pursuant to a 10b5-1 Trading Plan adopted by the Reporting Person on October 14, 2025. |
Common Stock
|
1,200 |
| 2026-02-09 | Rosenbaum Michael George |
Director, Chief Executive Officer |
Sell↓
Filing footnotes — Common Stock (Direct)
Automatic sale pursuant to a 10b5-1 Trading Plan adopted by the Reporting Person on October 14, 2025. |
Common Stock
|
1,200 |
| 2026-02-02 | Rosenbaum Michael George |
Director, Chief Executive Officer |
Sell↓
Filing footnotes — Common Stock (Direct)
Automatic sale pursuant to a 10b5-1 Trading Plan adopted by the Reporting Person on October 14, 2025. |
Common Stock
|
1,200 |
| 2026-01-26 | Rosenbaum Michael George |
Director, Chief Executive Officer |
Sell↓
Filing footnotes — Common Stock (Direct)
Automatic sale pursuant to a 10b5-1 Trading Plan adopted by the Reporting Person on October 14, 2025. |
Common Stock
|
1,200 |
| 2026-01-20 | Rosenbaum Michael George |
Director, Chief Executive Officer |
Sell↓
Filing footnotes — Common Stock (Direct)
Automatic sale pursuant to a 10b5-1 Trading Plan adopted by the Reporting Person on October 14, 2025. |
Common Stock
|
1,200 |