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

Rhea-AI Filing Summary

Guidewire Software insider sale by CEO and director Michael G. Rosenbaum. The filing discloses an automatic sale of 1,400 shares of Guidewire common stock on 08/25/2025 at a reported price of $214.70 per share under a 10b5-1 trading plan adopted October 15, 2024. After the sale, the reporting person beneficially owned 224,668 shares. The form is signed by an attorney-in-fact on behalf of Mr. Rosenbaum and indicates the sale was executed pursuant to the written trading plan to satisfy Rule 10b5-1 affirmative defense conditions.

Positive

• Transaction executed under a 10b5-1 trading plan, which provides an affirmative defense and demonstrates procedural compliance
• Filing discloses specific post-transaction beneficial ownership (224,668 shares), giving transparency about insider holdings

Negative

• Insider sale by the Chief Executive Officer and Director may be interpreted by some investors as a reduction in insider exposure
• Sale reduces holdings by 1,400 shares, which could attract attention despite being reported as pre-planned

Insights

Securities Analyst

TL;DR: Routine, pre-planned sale by the CEO under a 10b5-1 plan; limited immediate signal about company fundamentals.

This Form 4 shows a single automatic disposition of 1,400 shares at $214.70 under a 10b5-1 plan adopted October 15, 2024, leaving the reporting person with 224,668 shares. Because the sale is identified as executed under a pre-established plan, it reduces the informational weight of the transaction as an insider "timing" signal. The transaction size relative to total holdings appears modest in absolute terms based on the remaining beneficial ownership reported. The filing is procedural and complies with Section 16 reporting requirements.

Corporate Governance Expert

TL;DR: Governance procedure followed: sale executed via attorney-in-fact under an established 10b5-1 plan.

The document documents compliance with insider trading policies by disclosing a sale under a Rule 10b5-1 trading plan and includes an attorney-in-fact signature. This is standard governance practice for insiders seeking to transact while managing regulatory risk. The filing provides clear disclosure of relationship to the issuer (Director and Chief Executive Officer) and the mechanics of the reported sale.

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)
08/25/2025

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	08/25/2025		S(1)		1,400	D	$214.7	224,668	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	08/25/2025
	** 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) insider Michael G. Rosenbaum do on 08/25/2025?

He sold 1,400 shares of Guidewire common stock on 08/25/2025 at a reported price of $214.70 per share.

Was the sale by the insider part of a pre-established trading plan?

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

How many Guidewire shares did Rosenbaum own after the reported transaction?

After the sale, the reporting person beneficially owned 224,668 shares.

What is Michael Rosenbaum's relationship to Guidewire Software?

The form lists him as both a Director and an Officer with the title Chief Executive Officer.

Who signed the Form 4 for Rosenbaum?

The Form 4 was signed by Winston King, Attorney-in-Fact for Michael George Rosenbaum on 08/25/2025.