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

Rhea-AI Filing Summary

Guidewire Software, Inc. (GWRE) filed a Form 4 disclosing that Chief Executive Officer and Director Michael George Rosenbaum sold 1,400 shares of common stock on 30 June 2025 at a weighted-average price of $236.89 per share. Gross proceeds total roughly $331,646. The transaction was executed under a pre-arranged Rule 10b5-1 trading plan adopted on 15 October 2024.

Following the sale, Rosenbaum’s direct beneficial ownership declined from 237,268 to 235,868 shares, representing an approximate 0.6 % reduction in his personal stake. No derivative securities were reported, and there were no additional insider transactions disclosed in this filing.

The moderate size of the sale relative to Rosenbaum’s remaining holdings and the existence of a 10b5-1 plan suggest routine portfolio diversification rather than a definitive negative signal. Nonetheless, investors often monitor any insider selling activity by key executives for potential sentiment clues.

Positive

• None.

Negative

• CEO insider sale: Even though small, selling by the chief executive can be interpreted as a mildly negative sentiment indicator.

Insights

Securities Analyst

TL;DR: CEO sold 1,400 GWRE shares (~$0.33M) via 10b5-1; impact limited.

The reported sale equals roughly 0.6 % of Rosenbaum’s ownership and an immaterial fraction of Guidewire’s 82 million shares outstanding. Because it was executed under an established 10b5-1 plan, the transaction likely reflects automated diversification rather than an assessment of future fundamentals. Insider sentiment screens may flag the sale, but the magnitude is too small to alter valuation models or forward estimates. Overall, the filing is informational with negligible earnings or cash-flow impact.

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)
06/30/2025

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	06/30/2025		S(1)		1,400	D	$236.89	235,868	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	06/30/2025
	** 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

How many GWRE shares did the CEO sell on 30 June 2025?

Michael George Rosenbaum sold 1,400 shares of Guidewire Software common stock.

What price did Guidewire's CEO receive for the shares?

The shares were sold at a weighted-average price of $236.89 each.

How large is the CEO's remaining stake in GWRE after the sale?

Rosenbaum now directly owns 235,868 shares of GWRE.

Was the insider sale part of a 10b5-1 trading plan?

Yes. The sale was executed automatically under a Rule 10b5-1 plan adopted on 15 Oct 2024.

Does the filing report any changes in derivative securities?

No. The Form 4 shows no derivative securities acquired or disposed of in this transaction.