King James Winston
SEC insider (Form 3/4/5 filer). CIK 0001586253. Chief Admin Officer, Gen Couns at Guidewire Software, Inc. (GWRE). 36 reported Form 4/5 transactions since Sep 2024; latest on Oct 9, 2026. Located in SAN MATEO, CA.
Companies King James Winston has filed insider reports for
- Guidewire Software, Inc. (GWRE): Officer, Chief Admin Officer, Gen Couns
King James Winston
CIK: 0001586253
Transaction Breakdown
High conviction signal
Position reduction
Derivative conversions
Compensation grants
Gifts, tax withholding, conversions, dispositions to the issuer and other codes
Companies & Roles (1)
Guidewire Software, Inc.
Discretionary Trading P&L
Holdings
Transaction History (36 total)
- Oct 9, 2026GWRE
Guidewire Software, Inc.
SaleDirect9.2K shares at avg. $168.00$1.5M - Sep 18, 2026GWRE
Guidewire Software, Inc.
SaleDirect1.4K shares at avg. $144.98$200K - Sep 17, 2026GWRE
Guidewire Software, Inc.
SaleDirect11.8K shares at avg. $144.47$1.7M - Sep 15, 2026GWRE
Guidewire Software, Inc.
ExerciseDirect19.7K shares- - Sep 11, 2026GWRE
Guidewire Software, Inc.
AwardDirect8K shares- - Jul 9, 2026GWRE
Guidewire Software, Inc.
SaleDirect1.7K shares at avg. $130.64$220K - Jun 16, 2026GWRE
Guidewire Software, Inc.
SaleDirect999 shares at avg. $118.74$119K - Mar 17, 2026GWRE
Guidewire Software, Inc.
SaleDirect1K shares at avg. $163.86$164K - Dec 18, 2025GWRE
Guidewire Software, Inc.
SaleDirect1.9K shares at avg. $195.00$363K - Dec 16, 2025GWRE
Guidewire Software, Inc.
SaleDirect1.5K shares at avg. $192.08$280K
| Type | Shares | Price | Ownership | |||
|---|---|---|---|---|---|---|
| Oct 9, 2026 | GWRE Guidewire Software, Inc. | Sale | 9,187 | $168.00 | $1,543,416 | Direct |
| Sep 18, 2026 | GWRE Guidewire Software, Inc. | Sale | 1,381 | $144.98 | $200,217 | Direct |
| Sep 17, 2026 | GWRE Guidewire Software, Inc. | Sale | 11,814 | $144.47 | $1,706,784 | Direct |
| Sep 15, 2026 | GWRE Guidewire Software, Inc. | Exercise | 19,701 | - | $0 | Direct |
| Sep 11, 2026 | GWRE Guidewire Software, Inc. | Award | 8,034 | - | $0 | Direct |
| Jul 9, 2026 | GWRE Guidewire Software, Inc. | Sale | 1,684 | $130.64 | $219,998 | Direct |
| Jun 16, 2026 | GWRE Guidewire Software, Inc. | Sale | 999 | $118.74 | $118,624 | Direct |
| Mar 17, 2026 | GWRE Guidewire Software, Inc. | Sale | 1,001 | $163.86 | $164,022 | Direct |
| Dec 18, 2025 | GWRE Guidewire Software, Inc. | Sale | 1,860 | $195.00 | $362,700 | Direct |
| Dec 16, 2025 | GWRE Guidewire Software, Inc. | Sale | 1,457 | $192.08 | $279,855 | Direct |
1-10 of 36 transactions