[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 09/02/2025 at a price of $214.30 per share under a 10b5-1 trading plan adopted on October 15, 2024. After the reported transaction Rosenbaum beneficially owned 223,268 shares. The Form 4 was submitted and signed by an attorney-in-fact, Winston King, on behalf of Rosenbaum.

Positive

• Sale executed under a 10b5-1 plan, indicating the transaction was pre-scheduled and intended to provide an affirmative defense
• Clear disclosure of post-transaction beneficial ownership (223,268 shares), aiding investor transparency
• Form filed and signed by attorney-in-fact, demonstrating executed compliance with filing formalities

Negative

• Reduction in insider ownership by 1,400 shares as a result of the sale

Insights

Securities Analyst

TL;DR: A routine, pre-scheduled insider sale under a 10b5-1 plan; transaction reduces holdings by 1,400 shares.

The filing documents a single non-derivative sale of 1,400 common shares at $214.30 per share executed on 09/02/2025. The seller is the CEO and a director, and the sale is identified as automatic under a 10b5-1 trading plan adopted on 10/15/2024. The filing also reports post-transaction beneficial ownership of 223,268 shares. From a market-impact perspective, the disclosed sale is specific and limited in size and is presented as pre-authorized rather than opportunistic.

Corporate Governance Expert

TL;DR: Disclosure aligns with Section 16 reporting and 10b5-1 compliance; executed by attorney-in-fact.

The Form 4 shows adherence to Section 16(a) reporting requirements and notes the use of an affirmative defense trading plan. The filing was submitted via an attorney-in-fact signature, indicating delegated execution. The disclosure of the plan adoption date and transaction code supports transparency in insider trading controls, without revealing additional governance changes.

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
Estimated average burden
hours per response:			0.5

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)
09/02/2025

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	09/02/2025		S(1)		1,400	D	$214.3	223,268	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	09/02/2025
	** 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 Guidewire (GWRE) CEO Michael Rosenbaum sell on 09/02/2025?

He sold 1,400 shares of Guidewire common stock at $214.30 per share on 09/02/2025.

Was the sale by the GWRE CEO part of a pre-scheduled trading plan?

Yes. The sale was an automatic sale pursuant to a 10b5-1 trading plan adopted on October 15, 2024.

How many Guidewire shares does Michael Rosenbaum beneficially own after the transaction?

Following the sale, Rosenbaum beneficially owned 223,268 shares.

Who signed the Form 4 filing for Michael Rosenbaum?

The Form 4 was signed by Winston King, Attorney-in-Fact, on behalf of Michael George Rosenbaum on 09/02/2025.

What is the reporting relationship of Michael Rosenbaum to Guidewire?

He is reported as both a Director and an Officer with the title Chief Executive Officer.