James Winston King

CIK: 0001586253

Transaction Breakdown

Open Market Buys (P)0 (0.0%)

High conviction signal

Open Market Sales (S)29 (80.6%)

Position reduction

Option Exercises (M)4 (11.1%)

Derivative conversions

Awards (A)3 (8.3%)

Compensation grants

Other (G, F, J, C, D, …)0 (0.0%)

Gifts, tax withholding, conversions, dispositions to the issuer and other codes

Companies & Roles (1)

GWRE

Guidewire Software, Inc.

Officer

Discretionary Trading P&L

Holdings

Transaction History (36 total)

GWRE
Guidewire Software, Inc.
Oct 9, 2026
Sale(S)
Direct
9.2K shares at avg. $168.00$1.5M
GWRE
Guidewire Software, Inc.
Sep 18, 2026
Sale(S)
Direct
1.4K shares at avg. $144.98$200K
GWRE
Guidewire Software, Inc.
Sep 17, 2026
Sale(S)
Direct
11.8K shares at avg. $144.47$1.7M
GWRE
Guidewire Software, Inc.
Sep 15, 2026
Exercise(M)
Direct
19.7K shares-
GWRE
Guidewire Software, Inc.
Sep 11, 2026
Award(A)
Direct
8K shares-
GWRE
Guidewire Software, Inc.
Jul 9, 2026
Sale(S)
Direct
1.7K shares at avg. $130.64$220K
GWRE
Guidewire Software, Inc.
Jun 16, 2026
Sale(S)
Direct
999 shares at avg. $118.74$119K
GWRE
Guidewire Software, Inc.
Mar 17, 2026
Sale(S)
Direct
1K shares at avg. $163.86$164K
GWRE
Guidewire Software, Inc.
Dec 18, 2025
Sale(S)
Direct
1.9K shares at avg. $195.00$363K
GWRE
Guidewire Software, Inc.
Dec 16, 2025
Sale(S)
Direct
1.5K shares at avg. $192.08$280K
GWRE
Guidewire Software, Inc.
Nov 17, 2025
Sale(S)
Direct
798 shares at avg. $222.54$178K
GWRE
Guidewire Software, Inc.
Oct 20, 2025
Sale(S)
Direct
798 shares at avg. $245.70$196K
GWRE
Guidewire Software, Inc.
Sep 18, 2025
Sale(S)
Direct
1.9K shares at avg. $249.35$484K
GWRE
Guidewire Software, Inc.
Sep 18, 2025
Sale(S)
Direct
1.9K shares at avg. $247.21$464K
GWRE
Guidewire Software, Inc.
Sep 18, 2025
Sale(S)
Direct
2.1K shares at avg. $250.12$537K
GWRE
Guidewire Software, Inc.
Sep 18, 2025
Sale(S)
Direct
1.2K shares at avg. $248.16$297K
GWRE
Guidewire Software, Inc.
Sep 16, 2025
Sale(S)
Direct
7.1K shares at avg. $242.87$1.7M
GWRE
Guidewire Software, Inc.
Sep 15, 2025
Exercise(M)
Direct
10.6K shares-
GWRE
Guidewire Software, Inc.
Sep 11, 2025
Award(A)
Direct
5.7K shares-
GWRE
Guidewire Software, Inc.
Aug 18, 2025
Sale(S)
Direct
799 shares at avg. $211.61$169K
GWRE
Guidewire Software, Inc.
Jul 14, 2025
Sale(S)
Direct
2.5K shares at avg. $220.65$548K
GWRE
Guidewire Software, Inc.
Jun 17, 2025
Sale(S)
Direct
1.2K shares at avg. $248.94$306K
GWRE
Guidewire Software, Inc.
Mar 19, 2025
Sale(S)
Direct
792 shares at avg. $194.61$154K
GWRE
Guidewire Software, Inc.
Mar 19, 2025
Sale(S)
Direct
841 shares at avg. $191.30$161K
GWRE
Guidewire Software, Inc.
Mar 19, 2025
Sale(S)
Direct
1.8K shares at avg. $193.51$354K

		Type	Shares	Price		Ownership
Oct 9, 2026	GWRE Guidewire Software, Inc.	Sale(S)	9,187	$168.00	$1,543,416	Direct
Sep 18, 2026	GWRE Guidewire Software, Inc.	Sale(S)	1,381	$144.98	$200,217	Direct
Sep 17, 2026	GWRE Guidewire Software, Inc.	Sale(S)	11,814	$144.47	$1,706,784	Direct
Sep 15, 2026	GWRE Guidewire Software, Inc.	Exercise(M)	19,701	-	$0	Direct
Sep 11, 2026	GWRE Guidewire Software, Inc.	Award(A)	8,034	-	$0	Direct
Jul 9, 2026	GWRE Guidewire Software, Inc.	Sale(S)	1,684	$130.64	$219,998	Direct
Jun 16, 2026	GWRE Guidewire Software, Inc.	Sale(S)	999	$118.74	$118,624	Direct
Mar 17, 2026	GWRE Guidewire Software, Inc.	Sale(S)	1,001	$163.86	$164,022	Direct
Dec 18, 2025	GWRE Guidewire Software, Inc.	Sale(S)	1,860	$195.00	$362,700	Direct
Dec 16, 2025	GWRE Guidewire Software, Inc.	Sale(S)	1,457	$192.08	$279,855	Direct
Nov 17, 2025	GWRE Guidewire Software, Inc.	Sale(S)	798	$222.54	$177,587	Direct
Oct 20, 2025	GWRE Guidewire Software, Inc.	Sale(S)	798	$245.70	$196,069	Direct
Sep 18, 2025	GWRE Guidewire Software, Inc.	Sale(S)	1,940	$249.35	$483,746	Direct
Sep 18, 2025	GWRE Guidewire Software, Inc.	Sale(S)	1,878	$247.21	$464,259	Direct
Sep 18, 2025	GWRE Guidewire Software, Inc.	Sale(S)	2,147	$250.12	$537,013	Direct
Sep 18, 2025	GWRE Guidewire Software, Inc.	Sale(S)	1,197	$248.16	$297,042	Direct
Sep 16, 2025	GWRE Guidewire Software, Inc.	Sale(S)	7,149	$242.87	$1,736,256	Direct
Sep 15, 2025	GWRE Guidewire Software, Inc.	Exercise(M)	10,597	-	-	Direct
Sep 11, 2025	GWRE Guidewire Software, Inc.	Award(A)	5,687	-	-	Direct
Aug 18, 2025	GWRE Guidewire Software, Inc.	Sale(S)	799	$211.61	$169,076	Direct
Jul 14, 2025	GWRE Guidewire Software, Inc.	Sale(S)	2,482	$220.65	$547,653	Direct
Jun 17, 2025	GWRE Guidewire Software, Inc.	Sale(S)	1,230	$248.94	$306,194	Direct
Mar 19, 2025	GWRE Guidewire Software, Inc.	Sale(S)	792	$194.61	$154,133	Direct
Mar 19, 2025	GWRE Guidewire Software, Inc.	Sale(S)	841	$191.30	$160,885	Direct
Mar 19, 2025	GWRE Guidewire Software, Inc.	Sale(S)	1,827	$193.51	$353,548	Direct

1-25 of 36 transactions

About King James Winston

King James Winston (SEC CIK 0001586253) files insider reports with the SEC as Chief Admin Officer, Gen Couns of Guidewire Software, Inc. (GWRE).

Signal8 holds 22 ownership filings by King James Winston, all Form 4s, filed between Sep 13, 2024 and Oct 13, 2026. Those filings report 36 transactions, from Sep 11, 2024 to Oct 9, 2026. Signal8's Form 4 history starts in Sep 2024.

The business address on King James Winston's filings is in SAN MATEO, CA.

Recent filings by King James Winston

Oct 9, 2026: Open-market sale of GWRE shares (Form 4, code S).
Sep 18, 2026: Open-market sale of GWRE shares (Form 4, code S).
Sep 17, 2026: Open-market sale of GWRE shares (Form 4, code S).
Sep 15, 2026: Option exercise of GWRE shares (Form 4, code M).
Sep 11, 2026: Grant or award of GWRE shares (Form 4, code A).

Other insiders filing for Guidewire Software, Inc. (GWRE)

Rosenbaum Michael George, Chief Executive Officer
Mullen John P, President
Peterson David Franklin, Chief Accounting Officer
Cooper Jeffrey Elliott, Chief Financial Officer
Vollert Karl Alexander, Director
Anquillare Mark V, Director

How to read Form 4 transaction codes