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

Rhea-AI Filing Summary

Guidewire Software, Inc. (GWRE) – Form 4 insider transaction

On 7 July 2025, Chief Executive Officer and Director Michael George Rosenbaum reported a single open-market sale of 1,400 shares of Guidewire common stock at a price of $230.70 per share. The filing indicates the sale was executed under a pre-arranged Rule 10b5-1 trading plan adopted on 15 October 2024.

Following the transaction, the CEO’s direct beneficial ownership stands at 234,468 shares, implying that the disposition represents roughly 0.6 % of his reported holdings. No derivative security activity was reported in Table II.

• Type of filing: Form 4 (Statement of Changes in Beneficial Ownership)
• Insider role: Chief Executive Officer & Director
• Transaction code: “S” – open-market sale
• Rule 10b5-1: Affirmative defence box checked; sale executed pursuant to a previously adopted plan

The limited size of the sale relative to the CEO’s remaining stake and the disclosure of a 10b5-1 plan reduce the probability that the trade signals a fundamental change in management’s outlook; nevertheless, insider sales by top executives are routinely monitored by investors for potential sentiment shifts.

Positive

• Transparent execution under a disclosed Rule 10b5-1 plan enhances governance credibility.
• CEO retains 234,468 shares, signalling continued alignment with shareholder interests.

Negative

• Insider sale by the CEO can be perceived as a mildly negative sentiment indicator, despite its small size.

Insights

Securities Analyst

TL;DR: CEO sells 1,400 GWRE shares (0.6 % stake) via 10b5-1; low dollar impact, neutral signal.

The Form 4 reveals a modest, pre-planned disposition. At ~$231 per share, proceeds equal about $324k—immaterial against both the CEO’s remaining 234k shares and Guidewire’s public float. Because the transaction is flagged as a 10b5-1 trade, it likely reflects routine diversification rather than a valuation call. From a market-impact view, the event is not materially negative but will be logged in insider-transaction screens. Continued large insider ownership (>230k shares) preserves alignment with shareholders.

Corporate Governance Expert

TL;DR: Small, disclosed sale under 10b5-1 supports governance transparency.

The filing demonstrates adherence to best practices: advance adoption of a Rule 10b5-1 plan, timely Form 4 submission, and full description of the automatic sale. The sale volume is limited, and the CEO remains a significant holder, which mitigates governance concerns about commitment. I view the action as governance-neutral; no red flags arise regarding control, related-party issues, or abrupt stake reductions.

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)
07/07/2025

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	07/07/2025		S(1)		1,400	D	$230.7	234,468	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	07/07/2025
	** 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 07/07/2025?

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

At what price were the GWRE shares sold?

The shares were sold at $230.70 per share.

What percentage of the CEO's holdings was sold?

The sale represents approximately 0.6 % of his reported 234,468-share stake.

Was the sale executed under a Rule 10b5-1 trading plan?

Yes. The filing states it was an automatic sale under a 10b5-1 plan adopted on 10/15/2024.

How many GWRE shares does the CEO now own?

After the transaction, he beneficially owns 234,468 shares directly.

Were any derivative securities involved in this Form 4?

No. Table II shows no derivative security activity for this filing.