Guidewire Software (GWRE) CEO logs 1,200-share 10b5-1 stock sale

Rhea-AI Filing Summary

Guidewire Software CEO Michael George Rosenbaum reported an open-market sale of 1,200 shares of Common Stock at an average price of $128.19 per share. After this transaction, he directly holds 210,406 shares.

The sale was executed automatically under a Rule 10b5-1 trading plan adopted by Rosenbaum on October 14, 2025, indicating it was pre-scheduled rather than a discretionary market-timing decision.

Insider Trade Summary 10b5-1

Net Seller: 1,200 shares ($153,828)

Net Sell 1 txn

Insider Rosenbaum Michael George

Role Chief Executive Officer

Sold 1,200 shs ($154K)

Type	Security	Shares	Price	Value
Sale	Common Stock	1,200	$128.19	$154K

Holdings After Transaction: Common Stock — 210,406 shares (Direct, null)

Footnotes (1)

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Key Figures

Shares sold: 1,200 shares Sale price: $128.19 per share Shares held after sale: 210,406 shares +2 more

5 metrics

Shares sold 1,200 shares Open-market sale of common stock

Sale price $128.19 per share Average price for the 1,200-share sale

Shares held after sale 210,406 shares Direct holdings following the transaction

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

Transaction date 2026-05-18 Date of the reported open-market sale

Key Terms

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

3 terms

Rule 10b5-1 Trading Plan financial

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

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; transaction_code_description: Sale in open market or private transaction"

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 for the non-derivative transaction reported"

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 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)
05/18/2026

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	05/18/2026		S(1)		1,200	D	$128.19	210,406	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	05/18/2026
	** 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 GWRE’s CEO report in this Form 4?

Guidewire Software’s CEO Michael George Rosenbaum reported selling 1,200 shares of Common Stock. The shares were sold in an open-market transaction at an average price of $128.19 per share, and the trade was executed automatically under a pre-arranged Rule 10b5-1 trading plan.

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

The CEO sold Guidewire shares at an average price of $128.19 per share. This price reflects the execution level for the 1,200-share open-market sale reported, giving investors a clear view of the transaction value disclosed in this Form 4 filing.

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

After the reported sale, the CEO directly holds 210,406 shares of Guidewire common stock. This shows that the 1,200 shares sold represent a relatively small portion of his total direct holdings as disclosed in the Form 4 transaction details.

Was the GWRE CEO’s share sale under a Rule 10b5-1 trading plan?

Yes. The footnote states the sale was automatic under a Rule 10b5-1 trading plan adopted on October 14, 2025. Such plans pre-schedule trades, indicating the sale timing was planned in advance rather than a new discretionary decision.

What type of transaction did the GWRE Form 4 disclose?

The Form 4 discloses an open-market sale of common stock by the CEO, coded as an “S” transaction. It involved 1,200 shares and is categorized as a non-derivative transaction, meaning it relates directly to common stock, not options or other derivatives.