[Form 4] Guidewire Software, Inc. Insider Trading Activity

Rhea-AI Filing Summary

James Winston King, Chief Administrative Officer and General Counsel of Guidewire Software (GWRE), reported the receipt and partial disposition of company stock following PSU vesting. On 09/15/2025 10,597 performance shares converted into 10,597 common shares. The next day, 09/16/2025, 7,149 shares were sold at an average price of $242.867 per share to cover taxes, reducing his beneficial ownership from 52,926 to 45,777 shares. The filing explains these PSUs reflect performance determinations: Part 1 achieved 101.8% of FY23 targets (adding 123 PSUs) with staggered time-based vesting, and Part 2 achieved 120% of FY25 targets (adding 1,377 PSUs) and met time-based vesting on 09/15/2025. The PSUs underlying the award convert into common stock and have an expiration date of 09/15/2032.

Positive

• 10,597 performance shares converted into common stock, reflecting realized compensation
• Performance conditions exceeded targets: 101.8% for FY23 and 120% for FY25, increasing PSUs earned
• Detailed disclosure provided on vesting schedule, performance adjustments, and PSU expiration (09/15/2032)

Negative

• 7,149 shares sold at an average of $242.867 to cover taxes, reducing direct beneficial ownership from 52,926 to 45,777

Insights

Financial Analyst

TL;DR: Routine insider vesting and tax-driven sale; performance targets exceeded, modest net increase in share count.

The report documents standard executive compensation mechanics: performance share units vested based on achievement of ARR targets, converting into 10,597 shares. A portion of those shares (7,149) were sold immediately to satisfy tax withholding, at an average sale price of $242.867 per share, which is consistent with employer tax-withholding practices. Beneficial ownership declined from 52,926 to 45,777 shares after the sale. The performance results—101.8% for FY23 and 120% for FY25—are material to the grant but the filing contains no financial performance metrics beyond those percentages.

Corporate Governance Expert

TL;DR: Disclosure aligns with Section 16 timing and explains performance and vesting; transactions are administrative and non-suspicious.

The Form 4 provides required detail: conversion of PSUs, precise share counts, tax-related disposition, and an explanation of performance determinations and vesting schedule. The filing cites the Compensation Committee's determinations and identifies the expiration date for the awards. There are no indications of non-compliance, derivative hedging, or changes in control provisions in this document; it is a routine insider reporting of compensation realization and tax-related sale.

SEC Form 4

FORM 4

UNITED STATES SECURITIES AND EXCHANGE COMMISSION
Washington, D.C. 20549

STATEMENT OF CHANGES IN BENEFICIAL OWNERSHIP

Filed pursuant to Section 16(a) of the Securities Exchange Act of 1934
or Section 30(h) of the Investment Company Act of 1940

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Check this box if no longer subject to Section 16. Form 4 or Form 5 obligations may continue. See Instruction 1(b).

Check this box to indicate that a transaction was made pursuant to a contract, instruction or written plan for the purchase or sale of equity securities of the issuer that is intended to satisfy the affirmative defense conditions of Rule 10b5-1(c). See Instruction 10.

1. Name and Address of Reporting Person^*

King James Winston

(Last) (First) (Middle)

C/O GUIDEWIRE SOFTWARE, INC.

970 PARK PL, SUITE 200

(Street)

SAN MATEO CA 94403

(City) (State) (Zip)

2. Issuer Name and Ticker or Trading Symbol
Guidewire Software, Inc. [ GWRE ]

5. Relationship of Reporting Person(s) to Issuer
(Check all applicable)

	Director		10% Owner
X	Officer (give title below)		Other (specify below)
	Chief Admin Officer, Gen Couns

3. Date of Earliest Transaction (Month/Day/Year)
09/15/2025

4. If Amendment, Date of Original Filed (Month/Day/Year)

6. Individual or Joint/Group Filing (Check Applicable Line)

X	Form filed by One Reporting Person
	Form filed by More than One Reporting Person

Table I - Non-Derivative Securities Acquired, Disposed of, or Beneficially Owned
1. Title of Security (Instr. 3)	2. Transaction Date (Month/Day/Year)	2A. Deemed Execution Date, if any (Month/Day/Year)	3. Transaction Code (Instr. 8)		4. Securities Acquired (A) or Disposed Of (D) (Instr. 3, 4 and 5)			5. Amount of Securities Beneficially Owned Following Reported Transaction(s) (Instr. 3 and 4)	6. Ownership Form: Direct (D) or Indirect (I) (Instr. 4)	7. Nature of Indirect Beneficial Ownership (Instr. 4)
			Code	V	Amount	(A) or (D)	Price
Common Stock	09/15/2025		M		10,597	A	$0	52,926	D
Common Stock	09/16/2025		S(1)		7,149	D	$242.867(2)	45,777	D

Table II - Derivative Securities Acquired, Disposed of, or Beneficially Owned (e.g., puts, calls, warrants, options, convertible securities)
1. Title of Derivative Security (Instr. 3)	2. Conversion or Exercise Price of Derivative Security	3. Transaction Date (Month/Day/Year)	3A. Deemed Execution Date, if any (Month/Day/Year)	4. Transaction Code (Instr. 8)		5. Number of Derivative Securities Acquired (A) or Disposed of (D) (Instr. 3, 4 and 5)		6. Date Exercisable and Expiration Date (Month/Day/Year)		7. Title and Amount of Securities Underlying Derivative Security (Instr. 3 and 4)		8. Price of Derivative Security (Instr. 5)	9. Number of derivative Securities Beneficially Owned Following Reported Transaction(s) (Instr. 4)	10. Ownership Form: Direct (D) or Indirect (I) (Instr. 4)	11. Nature of Indirect Beneficial Ownership (Instr. 4)
				Code	V	(A)	(D)	Date Exercisable	Expiration Date	Title	Amount or Number of Shares
Performance Shares	$0	09/15/2025		M			10,597(3)	(3)	09/15/2032	Common Stock	10,597	$0	0	D

Explanation of Responses:

1. Shares sold by Issuer to cover taxes associated with settlement of Restricted Stock Units.

2. 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.

3. 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.

Remarks:

	/s/ James Winston King	09/17/2025
	** Signature of Reporting Person	Date
Reminder: Report on a separate line for each class of securities beneficially owned directly or indirectly.
* If the form is filed by more than one reporting person, see Instruction 4 (b)(v).
** Intentional misstatements or omissions of facts constitute Federal Criminal Violations See 18 U.S.C. 1001 and 15 U.S.C. 78ff(a).
Note: File three copies of this Form, one of which must be manually signed. If space is insufficient, see Instruction 6 for procedure.
Persons who respond to the collection of information contained in this form are not required to respond unless the form displays a currently valid OMB Number.

FAQ

What transactions did James Winston King report on the GWRE Form 4?

The filing reports conversion of 10,597 performance shares into common stock on 09/15/2025 and a sale of 7,149 shares on 09/16/2025 to cover taxes.

How many GWRE shares does the reporting person beneficially own after the transactions?

Following the reported transactions, the reporting person beneficially owned 45,777 shares.

At what price were the shares sold to cover taxes?

The sale price averaged $242.867 per share, with individual sale prices ranging from $242.8643 to $242.8692.

Why did the reporting person receive 10,597 shares?

Those shares resulted from vested performance share units after Compensation Committee determinations that performance targets were exceeded for FY23 and FY25.

When do the underlying PSUs expire and what is the vesting detail?

The PSUs have an expiration date of 09/15/2032. Part 1 had staggered time-based vesting (33% immediate, 33% at Year 2, 33% at Year 3); Part 2 met time-based vesting on 09/15/2025.