[Form 4] GUIDEWIRE SOFTWARE, INC. Insider Trading Activity

Rhea-AI Filing Summary

Michael George Rosenbaum, Chief Executive Officer and Director of Guidewire Software, Inc. (GWRE), reported an automatic sale of 1,400 shares of the issuer's common stock on 09/08/2025 at a price of $261.28 per share under a pre-existing 10b5-1 trading plan. Following the reported transaction, the filing shows the reporting person beneficially owned 221,868 shares, held directly.

The Form 4 was submitted as a single-person filing and was signed by an attorney-in-fact on behalf of Mr. Rosenbaum on 09/09/2025. The disclosure is limited to this single non-derivative sale and notes the sale was automatic pursuant to the trading plan adopted on 10/15/2024.

Positive

• Sale executed under a 10b5-1 plan, indicating the transaction was pre-planned and automatic
• Detailed disclosure provided: transaction date, price ($261.28), shares sold (1,400), and post-transaction ownership (221,868 shares)
• Reporting person retains significant direct ownership of 221,868 shares after the sale

Negative

• Reporting person disposed of 1,400 shares which reduces direct holdings

Insights

Financial Analyst

TL;DR: CEO executed an automatic sale of 1,400 shares under a 10b5-1 plan; retains significant direct ownership of 221,868 shares.

The Form 4 reports a routine, pre-planned disposition rather than an ad-hoc trade, which typically reduces concerns about opportunistic insider timing. The sale size (1,400 shares) is disclosed with the execution price of $261.28 and leaves the reporting person with 221,868 shares directly beneficially owned. From a capital-markets perspective this is a limited reduction in holdings and consistent with scheduled liquidity under an approved plan.

Corporate Governance Expert

TL;DR: Transaction executed under an established 10b5-1 plan, documented properly on Form 4 and countersigned by attorney-in-fact.

The filing clearly identifies the relationship (Director and CEO), the automatic nature of the sale pursuant to a 10b5-1 trading plan adopted on October 15, 2024, and includes the required signature by an attorney-in-fact dated September 9, 2025. Documentation meets standard disclosure requirements for Section 16 reporting: transaction code, number of shares sold, price per share, and post-transaction beneficial ownership are all provided.

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).

X

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)
09/08/2025

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	09/08/2025		S(1)		1,400	D	$261.28	221,868	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

Explanation of Responses:

1. Automatic sale pursuant to a 10b5-1 Trading Plan adopted by the Reporting Person on October 15, 2024.

Remarks:

	By: Winston King, Attorney-in-Fact for Michael George Rosenbaum	09/09/2025
	** 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 did GWRE CEO Michael Rosenbaum report on Form 4?

The Form 4 reports an automatic sale of 1,400 shares of Guidewire Software (GWRE) on 09/08/2025 at $261.28 per share under a 10b5-1 trading plan.

How many GWRE shares does Michael Rosenbaum own after the reported transaction?

The filing shows the reporting person beneficially owned 221,868 shares following the reported sale.

Was the sale by the GWRE insider spontaneous or pre-planned?

The sale was automatic and executed pursuant to a 10b5-1 trading plan adopted by the reporting person on 10/15/2024.

What price was reported for the GWRE share sale?

The reported sale price was $261.28 per share.

When was the Form 4 signed and filed?

The signature on the Form 4 is by an attorney-in-fact dated 09/09/2025; the transaction date reported is 09/08/2025.