James Winston King - 15 Sep 2025 Form 4 Insider Report for Guidewire Software, Inc. (GWRE)

Role: Chief Admin Officer, Gen Couns
Signature: /s/ James Winston King
Issuer symbol: GWRE
Transactions as of: 15 Sep 2025
Net transactions value: -$1,736,256
Form type: 4
Filing time: 17 Sep 2025, 19:27:48 UTC
Previous filing: 15 Sep 2025
Next filing: 22 Sep 2025
SEC: View on sec.gov

Reporting Owners (1)

Name	Relationship	Address	Signature	Signature date	CIK
King James Winston	Chief Admin Officer, Gen Couns	C/O GUIDEWIRE SOFTWARE, INC., 970 PARK PL, SUITE 200, SAN MATEO	/s/ James Winston King	17 Sep 2025	0001586253

Transactions Table

Type	Sym	Class	Transaction	Value $	Shares	Change %	* Price $	Shares After	Date	Ownership	Footnotes
transaction	GWRE	Common Stock	Options Exercise	$0	+10,597	+25%	$0.000000	52,926	15 Sep 2025	Direct
transaction	GWRE	Common Stock	Sale	$1,736,256	-7,149	-14%	$242.87	45,777	16 Sep 2025	Direct	F1, F2

Derivative Securities (e.g., puts, calls, warrants, options, convertible securities)

Type	Sym	Class	Transaction	Value $	Shares	Change %	* Price $	Shares After	Date	Underlying Class	Amount	Exercise Price	Ownership	Footnotes
transaction	GWRE	Performance Shares	Options Exercise	$0	-10,597	-100%	$0.000000	0	15 Sep 2025	Common Stock	10,597	$0.000000	Direct	F3

* An asterisk sign (*) next to the price indicates that the price is likely invalid.

Explanation of Responses:

Id	Content
F1	Shares sold by Issuer to cover taxes associated with settlement of Restricted Stock Units.
F2	The sale price reported in column 4 of Table 1 represents the average sale price of the shares sold ranging from $242.8643 to $242.8692 per share. The reporting person will provide, upon request by the Commission staff, the Issuer, or a security holder of the Issuer, full information regarding the number of shares sold at each separate price.
F3	At the end of Year 1, as to 50% of this PSU award (Part 1), the Compensation Committee of the Board of Directors (Compensation Committee) determined, on September 15, 2023, that 101.8% of the performance conditions against the FY23 ARR targets were met resulting in an increase of 123 PSUs earned by the Reporting Person. 33% of Part 1 vested immediately thereafter. 33% of Part 1 will vest at the end of Year 2, and 33% of Part 1 will vest at the end of Year 3. At the end of Year 3, as to 50% of this PSU award (Part 2), the Compensation Committee determined, on September 10, 2025, that 120% of the performance conditions against the FY25 ARR targets were met resulting in an increase of 1,377 PSUs earned by the Reporting Person. Part 2 met its time-based vesting on September 15, 2025.