Guidewire (GWRE) CEO logs small 1,200-share sale under 10b5-1 plan

Rhea-AI Filing Summary

Guidewire Software, Inc. Chief Executive Officer Michael George Rosenbaum reported an open-market sale of common stock. He sold 1,200 shares at a price of $138.51 per share and held 209,206 shares of common stock directly after the transaction. According to a footnote, this was an automatic sale made under a pre-arranged Rule 10b5-1 trading plan adopted by the reporting person.

Insights

Equity compensation and insider-trading analyst

CEO's small, pre-planned stock sale appears routine and limited in size.

Chief Executive Officer Michael George Rosenbaum sold 1,200 shares of Guidewire Software, Inc. common stock at $138.51 per share. Following the sale, he directly owns 209,206 shares, indicating that only a small fraction of his reported holdings was sold in this transaction.

A footnote explains the sale was executed automatically under a Rule 10b5-1 trading plan. Such plans are established in advance and are designed to systematize trading, which generally reduces the informational value of the sale’s timing for assessing management’s view of the stock.

Insider Trade Summary 10b5-1

Net Seller: 1,200 shares ($166,212)

Net Sell 1 txn

Insider Rosenbaum Michael George

Role Chief Executive Officer

Sold 1,200 shs ($166K)

Type	Security	Shares	Price	Value
Sale	Common Stock	1,200	$138.51	$166K

Holdings After Transaction: Common Stock — 209,206 shares (Direct, null)

Footnotes (1)

1. [object Object]

Key Figures

Shares sold: 1,200 shares Sale price: $138.51 per share Shares held after sale: 209,206 shares +1 more

4 metrics

Shares sold 1,200 shares Open-market sale of common stock on 2026-05-26

Sale price $138.51 per share Price for the 1,200 shares of common stock sold

Shares held after sale 209,206 shares Direct common stock ownership following the transaction

Net buy/sell shares -1,200 shares Net effect of reported transactions in this Form 4

Key Terms

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

4 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

"Guidewire Software reported the sale in a Form 4 insider trading report"

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.

Form 4 Insider Transactions: What Each Field Means →

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)
05/26/2026

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	05/26/2026		S(1)		1,200	D	$138.51	209,206	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	05/26/2026
	** 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)

FAQ

What insider transaction did Guidewire Software (GWRE) report for its CEO?

Guidewire Software reported that CEO Michael George Rosenbaum sold 1,200 shares of common stock. The shares were sold in an open-market transaction at a price of $138.51 per share, and the sale was disclosed in a Form 4 insider trading report.

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

The CEO’s shares were sold at an average price of $138.51 per share. This price reflects the execution level for the 1,200 shares sold in the open market, as reported in the Form 4 transaction details filed with regulators.

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

After selling 1,200 shares, CEO Michael George Rosenbaum directly holds 209,206 shares of Guidewire common stock. This post-transaction holding is disclosed in the Form 4 and shows he retained the large majority of his reported equity position.

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

Yes. A footnote states the sale was automatic under a Rule 10b5-1 Trading Plan adopted by the reporting person. Such pre-arranged plans schedule trades in advance, helping separate personal portfolio decisions from non-public information concerns.

Does the Guidewire (GWRE) Form 4 show any option exercises or derivative trades?

No derivative transactions are listed in the summarized data. The Form 4 excerpt shows a single non-derivative transaction: an open-market sale of 1,200 shares of common stock by the CEO, with no option exercises reported in this specific filing.