As of September 05, 2026, Guidewire Software's top three insider holders are Michael George Rosenbaum (Chief Executive Officer, 190.18K shares), John P Mullen (President, 113.11K shares), Jeffrey Elliott Cooper (Chief Financial Officer, 62.12K shares).
| # | Insider | Position | Direct | Indirect | Total | Share of Insiders | Last Filed |
|---|---|---|---|---|---|---|---|
| 1 | Michael George Rosenbaum | Chief Executive Officer | 190,176 | 0 | 190,176 | 35.7% | 10 Aug, 2026 |
| 2 | John P Mullen | President | 113,115 | 0 | 113,115 | 21.2% | 26 Aug, 2026 |
| 3 | Jeffrey Elliott Cooper | Chief Financial Officer | 62,119 | 0 | 62,119 | 11.7% | 22 Jun, 2026 |
| 4 | James Winston King | Chief Admin Officer, Gen Couns | 30,018 | 0 | 30,018 | 5.6% | 09 Jul, 2026 |
| 5 | Frank E Jr Odowd | Chief Sales Officer | 28,275 | 0 | 28,275 | 5.3% | 21 Sep, 2021 |
| 6 | Margaret Dillon | Director | 16,393 | 0 | 16,393 | 3.1% | 16 Dec, 2025 |
| 7 | Catherine P Lego | Director | 14,393 | 0 | 14,393 | 2.7% | 16 Dec, 2025 |
| 8 | Paul Lavin | Director | 1,211 | 12,585 | 13,796 | 2.6% | 23 Dec, 2024 |
| 9 | Rajani Ramanathan | Director | 11,057 | 0 | 11,057 | 2.1% | 16 Dec, 2025 |
| 10 | Michael C Keller | Director | 10,606 | 0 | 10,606 | 2.0% | 16 Dec, 2025 |
| 11 | Marcus Ryu | Ceo And President | 10,555 | 0 | 10,555 | 2.0% | 19 Dec, 2023 |
| 12 | David Franklin Peterson | Chief Accounting Officer | 9,787 | 0 | 9,787 | 1.8% | 27 Aug, 2026 |
| 13 | Michael Polelle | Chief Delivery Officer | 7,241 | 0 | 7,241 | 1.4% | 18 Mar, 2022 |
| 14 | David S Bauer | Director | 7,099 | 0 | 7,099 | 1.3% | 16 Dec, 2025 |
| 15 | Mark V Anquillare | Director | 2,716 | 0 | 2,716 | 0.5% | 16 Dec, 2025 |
| 16 | Andrew William Fraser Brown | Director | 2,524 | 0 | 2,524 | 0.5% | 23 Jun, 2022 |
| 17 | Jeffrey Steven Sloan | Director | 2,371 | 0 | 2,371 | 0.4% | 16 Dec, 2025 |
| 18 | Karl Alexander Vollert | Director | 578 | 0 | 578 | 0.1% | 12 Aug, 2026 |
Each row is that insider’s most recently reported position, from Form 4 filings over the last 60 months — which is why this total does not tie to the quarterly series above, where a quarter counts only the insiders who filed in it. Shares held through a fund or institutional portfolio are counted on the institutional ownership page instead.
| Date | Insider | Position | Transaction | Shares | Price | Value | Shares Held After | Ownership |
|---|---|---|---|---|---|---|---|---|
| 31 Aug, 2026 | Michael George Rosenbaum | Chief Executive Officer | Disposed S | 1,200 | $204.44 | $245.33K | 186,576 | Direct |
| 27 Aug, 2026 | David Franklin Peterson | Chief Accounting Officer | Disposed S | 2,500 | $200.00 | $500.00K | 9,787 | Direct |
| 19 Aug, 2026 | John P Mullen | President | Disposed S | 16,200 | $185.00 | $3.00Mn | 114,915 | Direct |
| 25 Aug, 2026 | John P Mullen | President | Disposed S | 1,800 | $188.46 | $339.23K | 113,115 | Direct |
| 24 Aug, 2026 | Michael George Rosenbaum | Chief Executive Officer | Disposed S | 1,200 | $187.82 | $225.38K | 187,776 | Direct |
| 19 Aug, 2026 | John P Mullen | President | Disposed S | 14,400 | $185.00 | $2.66Mn | 116,715 | Direct |
| 17 Aug, 2026 | Michael George Rosenbaum | Chief Executive Officer | Disposed S | 1,200 | $172.88 | $207.46K | 188,976 | Direct |
| 12 Aug, 2026 | Karl Alexander Vollert | Director | Acquired A | 578 | $0.00 | $0 | 578 | Direct |
| 10 Aug, 2026 | Michael George Rosenbaum | Chief Executive Officer | Disposed S | 1,200 | $169.50 | $203.40K | 190,176 | Direct |
| 03 Aug, 2026 | Michael George Rosenbaum | Chief Executive Officer | Disposed S | 1,200 | $155.92 | $187.10K | 191,376 | Direct |
| 27 Jul, 2026 | Michael George Rosenbaum | Chief Executive Officer | Disposed S | 1,200 | $142.31 | $170.77K | 192,576 | Direct |
| 20 Jul, 2026 | Michael George Rosenbaum | Chief Executive Officer | Disposed S | 1,200 | $147.42 | $176.90K | 193,776 | Direct |
| 13 Jul, 2026 | Michael George Rosenbaum | Chief Executive Officer | Disposed S | 1,200 | $138.47 | $166.16K | 194,976 | Direct |
| 09 Jul, 2026 | James Winston King | Chief Admin Officer, Gen Couns | Disposed S | 1,684 | $130.64 | $220.00K | 30,018 | Direct |
| 06 Jul, 2026 | Michael George Rosenbaum | Chief Executive Officer | Disposed S | 1,200 | $131.63 | $157.96K | 196,176 | Direct |
| 29 Jun, 2026 | Michael George Rosenbaum | Chief Executive Officer | Disposed S | 1,200 | $124.29 | $149.15K | 197,376 | Direct |
| 22 Jun, 2026 | Michael George Rosenbaum | Chief Executive Officer | Disposed S | 1,200 | $105.67 | $126.80K | 198,576 | Direct |
| 22 Jun, 2026 | Jeffrey Elliott Cooper | Chief Financial Officer | Disposed S | 1,348 | $105.67 | $142.44K | 62,119 | Direct |
| 16 Jun, 2026 | John P Mullen | President | Disposed S | 4,292 | $118.74 | $509.64K | 131,115 | Direct |
| 15 Jun, 2026 | Michael George Rosenbaum | Chief Executive Officer | Disposed S | 1,200 | $123.85 | $148.62K | 205,606 | Direct |