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

Rhea-AI Filing Summary

Jeffrey Elliott Cooper, Chief Financial Officer of Guidewire Software, Inc. (GWRE), received 21,194 performance shares on September 15, 2025 as a result of vested performance-based awards and plan mechanics, increasing his beneficial ownership to 98,749 shares. The award description notes earlier adjustments: 249 PSUs were added after FY23 performance and an additional 2,754 PSUs were credited after FY25 performance. On September 16, 2025 Cooper sold 14,103 shares to cover taxes related to RSU settlement at an average sale price of approximately $242.8668 per share, leaving him with 84,646 shares beneficially owned. The performance share award underlying the 21,194 shares is exercisable and converts into common stock and has an indicated expiration/action date of September 15, 2032.

Positive

• Performance-based awards were credited: an increase of 2,754 PSUs credited for FY25 performance (120% of target).
• Prior FY23 adjustment added 249 PSUs after a 101.8% achievement of FY23 ARR targets.
• 21,194 performance shares were issued on September 15, 2025, reflecting compensation tied to company ARR performance.

Negative

• 14,103 shares were sold on September 16, 2025 (tax-withholding sale), reducing beneficial ownership from 98,749 to 84,646 shares.
• Sale price for the withholding sale averaged approximately $242.8668 per share, representing a material cash transaction by the reporting person.

Insights

Securities Analyst

TL;DR: CFO received material performance-based equity and executed a routine tax-cover sell; net holdings reduced after the sell.

The filings show the CFO was credited with 21,194 performance shares on September 15, 2025, reflecting strong performance vesting (including 2,754 PSUs from FY25 at 120% achievement). Such crediting is a positive signal about attainment of ARR performance targets tied to compensation. The immediate subsequent sale of 14,103 shares on September 16, 2025, was disclosed as a tax-withholding sale tied to RSU settlement and occurred at an average price of ~$242.8668 per share. Net beneficial ownership moved from 98,749 shares pre-sale to 84,646 shares post-sale. These are standard executive compensation transactions with limited implications beyond confirming achievement of performance metrics and routine tax mechanics.

Corporate Governance Expert

TL;DR: Performance criteria met and Compensation Committee actions resulted in sizable PSU vesting; subsequent sell was administrative.

The report documents Compensation Committee determinations: Part 1 (FY23) resulted in a 101.8% payout (adding 249 PSUs) with staggered time-based vesting, and Part 2 (FY25) achieved 120% of targets adding 2,754 PSUs that met time-based vesting on September 15, 2025. The structure described (performance then time-based vesting) aligns pay with multi-year ARR targets. The disclosed sale on September 16, 2025, was for tax withholding purposes, a common mechanism to satisfy tax obligations on equity settlements. No non-routine trading patterns or flagged related-party issues are disclosed in the form.

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

OMB APPROVAL

OMB Number:			3235-0287
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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^*

Cooper Jeffrey Elliott

(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 Financial Officer

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		21,194	A	$0	98,749	D
Common Stock	09/16/2025		S(1)		14,103	D	$242.8668(2)	84,646	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			21,194(3)	(3)	09/15/2032	Common Stock	21,194	$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 $242.8664 to $242.8687 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 249 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 2,754 PSUs earned by the Reporting Person. Part 2 met its time-based vesting on September 15, 2025.

Remarks:

	By: Winston King, Attorney-in-Fact for Jeffrey Elliott Cooper	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.
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FAQ

What transactions did GWRE CFO Jeffrey Cooper report on Form 4?

The Form 4 reports receipt of 21,194 performance shares on September 15, 2025 and a sale of 14,103 shares on September 16, 2025 to cover taxes.

How many shares does Jeffrey Cooper beneficially own after these transactions (GWRE)?

Following the September 16, 2025 sale, the filing reports 84,646 shares beneficially owned by the reporting person.

Why were performance shares credited to the CFO?

The filing states Compensation Committee determinations: Part 1 (FY23) achieved 101.8% of ARR targets adding 249 PSUs; Part 2 (FY25) achieved 120% adding 2,754 PSUs that vested on September 15, 2025.

What was the price for the shares sold to cover taxes?

The average sale price for the tax-withholding sale on September 16, 2025, was approximately $242.8668 per share, with reported sale prices ranging from $242.8664 to $242.8687.

Are the performance shares subject to future vesting or expiration?

The filing indicates the performance shares involved are tied to a schedule with an indicated date of September 15, 2032 for the referenced award mechanics.