Guidewire CEO sells 1,200 shares in planned trade

Guidewire Software, Inc. Chief Executive Officer Michael George Rosenbaum reported an open-market sale of 1,200 shares of common stock at $135.62 per share.

Rhea-AI Filing Summary

Guidewire Software, Inc. Chief Executive Officer Michael George Rosenbaum reported an open-market sale of 1,200 shares of common stock at $135.62 per share. The transaction was executed pursuant to a pre-arranged Rule 10b5-1 trading plan adopted on October 14, 2025.

Following this sale, Rosenbaum directly holds 206,806 shares of Guidewire common stock, reflecting his continuing equity stake in the company while allowing for planned portfolio diversification through scheduled sales.

Insider Trade Summary 10b5-1

Net Seller: 1,200 shares

Net Sell 1 txn

Insider Rosenbaum Michael George

Role Chief Executive Officer

Sold 1,200 shs ($163K)

Type	Security	Shares	Price	Value
Sale	Common Stock	1,200	$135.62	$163K

Holdings After Transaction: Common Stock — 206,806 shares (Direct)

Footnotes (1)

1. F1. Automatic sale pursuant to a 10b5-1 Trading Plan adopted by the Reporting Person on October 14, 2025.

Key Figures

Shares sold: 1,200 shares Sale price: $135.62 per share Shares held after: 206,806 shares +1 more

4 metrics

Shares sold 1,200 shares Open-market sale on June 8, 2026

Sale price $135.62 per share Price for the 1,200 shares sold

Shares held after 206,806 shares Direct holdings following the transaction

Net shares sold 1,200 shares Net sell direction in transaction summary

Key Terms

Rule 10b5-1 Trading Plan, open-market sale, Common Stock, Form 4, +1 more

5 terms

Rule 10b5-1 Trading Plan regulatory

"Automatic sale pursuant to a 10b5-1 Trading Plan adopted by the Reporting Person"

A Rule 10b5-1 trading plan is a pre-arranged schedule that allows company insiders to buy or sell stock at specific times, even if they have inside information. It helps prevent accusations of unfair trading by making these transactions look planned and transparent, rather than sneaky or illegal.

open-market sale financial

"transaction_action: open-market sale"

An open-market sale is when a shareholder sells existing shares directly on a public exchange to any willing buyer, rather than through a private deal. Think of it like putting goods on a busy market stall where price is set by supply and demand; for investors it matters because such sales increase available supply, can put short-term downward pressure on the stock price, and signal changes in liquidity or investor confidence.

Common Stock financial

"security_title: Common Stock"

Common stock represents ownership shares in a company, giving investors a stake in its success and a say in important decisions through voting rights. It is the most common type of stock traded on markets and can provide income through dividends, as well as potential for value growth. For investors, holding common stock means sharing in the company’s profits and risks.

Form 4 regulatory

"INSIDER FILING DATA (Form 4)"

Form 4 is a official document that company insiders, such as executives or major shareholders, file with regulators whenever they buy or sell company shares. It provides transparency about how those with inside knowledge are trading, helping investors see if insiders are confident in the company's prospects or may be selling for personal reasons. This information can influence investor decisions by revealing insiders' perspectives on the company's value.

Chief Executive Officer financial

"officer_title: Chief Executive Officer"

A chief executive officer (CEO) is the top leader of a company, responsible for making major decisions, setting goals, and guiding the organization’s overall direction. Think of the CEO as the captain of a ship, steering it toward success. Investors pay close attention to the CEO because their leadership and strategy can significantly influence the company's performance and future growth.

FAQ

AI-generated questions and answers. How Rhea-AI works. Not financial advice.

What insider transaction did Guidewire (GWRE) report in this Form 4?

Guidewire reported that CEO Michael George Rosenbaum sold 1,200 shares of common stock. The shares were sold in an open-market transaction at a reported price of $135.62 per share, as disclosed in the Form 4 filing.

At what price did the Guidewire (GWRE) CEO sell shares?

The CEO’s 1,200 Guidewire shares were sold at $135.62 per share. This price reflects the execution level for the reported open-market transaction, providing investors with a clear reference point for the insider sale.

How many Guidewire (GWRE) shares does the CEO hold after the sale?

After the reported transaction, CEO Michael George Rosenbaum directly holds 206,806 Guidewire shares. This post-transaction holding shows he retains a significant ownership position despite the relatively small sale disclosed.

Was the Guidewire (GWRE) CEO sale under a Rule 10b5-1 trading plan?

Yes. The Form 4 notes the sale occurred under a Rule 10b5-1 trading plan. The plan was adopted on October 14, 2025, indicating the transaction was pre-scheduled rather than opportunistic market timing.

How large was the Guidewire (GWRE) CEO’s sale compared to his holdings?

The CEO sold 1,200 shares while reporting 206,806 shares owned afterward. This indicates only a small portion of his total reported direct holdings was sold in the disclosed transaction.

AI-generated analysis. How Rhea-AI works. Not financial advice.

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Accepted by SEC EDGAR 06/08/2026 - 04:42 PM EDT Learn about SEC filing dates

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 CALIFORNIA 94403

(City) (State) (Zip)

UNITED STATES

(Country)

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

2a. Foreign Trading Symbol

3. Date of Earliest Transaction (Month/Day/Year)
06/08/2026

6. Individual or Joint/Group Filing (Check Applicable Line)

X	Form filed by One Reporting Person
	Form filed by More than One Reporting Person

4. If Amendment, Date of Original Filed (Month/Day/Year)

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	06/08/2026		S(1)		1,200	D	$135.62	206,806	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 14, 2025.

Remarks:

	By: Winston King, Attorney-in-Fact for Michael George Rosenbaum	06/08/2026
	** 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.
* Form 4: SEC 1474 (03-26)