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

Rhea-AI Filing Summary

Michael George Rosenbaum, CEO and a director of Guidewire Software, reported changes in his beneficial ownership following performance-share vesting and a sale to cover taxes. On 09/15/2025 the reporting person was issued 45,849 performance shares (PSUs) deemed earned and immediately vested as to Part 2, increasing his direct beneficial ownership to 295,275 shares. On 09/16/2025 he sold 30,317 shares at an average price of approximately $242.8659 per share to cover taxes, leaving 264,958 shares beneficially owned. The filing states the PSUs reflect above-target performance (including a prior 101.8% achievement for FY23 and 120% for FY25) and notes the sale was to satisfy tax withholding on RSU settlement.

Positive

• Performance-based PSU issuance: 45,849 PSUs were issued following above-target performance (101.8% for FY23 component and 120% for FY25 component), indicating payout aligned with ARR goals
• Detailed disclosure: The filing specifies the number of shares, average sale price range for tax-withholding shares, and explains vesting and performance outcomes

Negative

• None.

Insights

Financial Analyst

TL;DR: Routine insider vesting and tax-related sale; performance metrics exceeded targets, resulting in meaningful PSU issuance.

The filing shows management compensation linked to ARR performance metrics: Part 1 and Part 2 of the PSU award exceeded targets (101.8% and 120%), producing additional earned PSUs. The immediate vesting of 45,849 PSUs on 09/15/2025 materially increased the CEO's direct stake to 295,275 shares. The subsequent sale of 30,317 shares on 09/16/2025 at an average price of $242.8659 appears to be a mechanical, tax-withholding transaction rather than a signal of opportunistic diversification. Overall, these transactions are consistent with performance-driven equity compensation and routine tax settlements, producing a neutral near-term market implication.

Corporate Governance Expert

TL;DR: Governance practices show pay-for-performance alignment; disclosure is specific about performance determinations and tax withholding sale.

The Form 4 discloses that the Compensation Committee certified performance against FY23 and FY25 ARR targets, increasing PSU awards and triggering time-based vesting. The report includes clear explanations of the sell-to-cover mechanics and provides the average sale price range. From a governance perspective, this demonstrates transparent linkage between pay and measurable targets and timely disclosure of related insider transactions.

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^*

Rosenbaum Michael George

(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)

X	Director		10% Owner
X	Officer (give title below)		Other (specify below)
	Chief Executive 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		45,849	A	$0	295,275	D
Common Stock	09/16/2025		S(1)		30,317	D	$242.8659(2)	264,958	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			45,849(3)	(3)	09/15/2032	Common Stock	45,849	$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 $242.8649 to $242.8684 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 537 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 5,957 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 Michael George Rosenbaum	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).
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FAQ

What insider transactions did Guidewire (GWRE) report for CEO Michael Rosenbaum?

On 09/15/2025 the CEO received 45,849 performance shares, and on 09/16/2025 he sold 30,317 shares to cover taxes at an average price of about $242.8659 per share.

Why were performance shares issued to the CEO in this Form 4?

The Compensation Committee certified that PSU performance targets tied to FY23 and FY25 ARR were met above target (101.8% and 120%), increasing the number of PSUs earned.

How many shares does Michael Rosenbaum beneficially own after these transactions?

Following the reported transactions the filing shows 264,958 shares beneficially owned after the sell-to-cover; prior to the sale ownership was reported as 295,275 shares.

What was the purpose of the 30,317-share sale reported on 09/16/2025?

The shares were sold by the issuer to cover taxes associated with the settlement of restricted stock units, per the filing's explanation.

At what price were the tax-withholding shares sold?

Average sale price reported was approximately $242.8659 per share, with the filing noting a range from $242.8649 to $242.8684 and offering to provide per-price details on request.