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

Rhea-AI Filing Summary

Michael George Rosenbaum, Guidewire Software, Inc. (GWRE) Chief Executive Officer and director, reported a sale of 1,400 shares of Common Stock on 09/29/2025 at a price of $232.25 per share. After the sale he beneficially owns 262,158 shares. The filing states the sale was an automatic sale pursuant to a 10b5-1 trading plan that Mr. Rosenbaum adopted on October 15, 2024. The Form 4 was executed by Winston King as attorney-in-fact for Mr. Rosenbaum and reflects a routine reported change in beneficial ownership by an insider.

Positive

• Sale executed under a 10b5-1 trading plan, indicating pre-established, rule-compliant insider trading procedures
• Reporting shows continued significant insider ownership with 262,158 shares remaining beneficially owned

Negative

• Insider disposition of shares: 1,400 shares were sold, reducing beneficial holdings
• Form 4 reports only a single transaction; no additional context on frequency or total plan size is provided

Insights

Securities/Financial Analyst

TL;DR: Insider sold a small block under a pre-set 10b5-1 plan; ownership remains sizable at 262,158 shares.

The reported disposition of 1,400 shares at $232.25 was executed under a 10b5-1 plan adopted October 15, 2024. This disclosure is consistent with planned, rule-compliant insider liquidity rather than an opportunistic trade. The remaining beneficial ownership (262,158 shares) continues to reflect meaningful insider exposure to company equity. No derivatives or additional transactions are reported.

Corporate Governance Expert

TL;DR: Use of a 10b5-1 plan indicates adherence to insider-trading controls; filing was properly executed by an attorney-in-fact.

The Form 4 discloses a sale governed by a previously adopted 10b5-1 trading plan, which supports procedural compliance with insider trading policies. The document includes an attorney-in-fact signature (Winston King), showing an executed power of attorney process. No amendments, option exercises, or additional indirect ownership notes appear in this filing.

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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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).

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)
09/29/2025

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	09/29/2025		S(1)		1,400	D	$232.25	262,158	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	09/29/2025
	** 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 insider Michael Rosenbaum sell on 09/29/2025?

He sold 1,400 shares of Guidewire Software common stock at $232.25 per share on 09/29/2025.

Why was the sale by GWRE's CEO executed?

The Form 4 states the sale was an automatic sale pursuant to a 10b5-1 trading plan adopted by the reporting person on October 15, 2024.

How many GWRE shares does Michael Rosenbaum beneficially own after the sale?

Following the reported transaction he beneficially owns 262,158 shares.

Who signed the Form 4 for Michael Rosenbaum?

The Form 4 was executed by Winston King, Attorney-in-Fact, on behalf of Michael George Rosenbaum on 09/29/2025.

Does the Form 4 show any derivative transactions for GWRE by Rosenbaum?

No. The filing contains only a non-derivative sale of common stock; Table II for derivatives shows no transactions.

Was this Form 4 an amendment or the earliest transaction date reported?

The filing lists 09/29/2025 as the date of the earliest transaction and does not indicate it is an amendment to a prior Form 4.