Guidewire CEO sells 73,490 shares in September

Guidewire Software’s CEO reported Rule 10b5-1 and tax-related sales totaling 73,490 shares of common stock.

Rhea-AI Filing Summary

Guidewire Software, Inc. (GWRE) reported that Chief Executive Officer and director Michael George Rosenbaum had two open-market sales of common stock. On September 17, 2026, 72,290 shares were sold at an average price of $144.4718 per share to cover taxes associated with Restricted Stock Unit settlement.

On September 21, 2026, an additional 1,200 shares were sold at $145.92 per share in an automatic transaction pursuant to a Rule 10b5-1 Trading Plan adopted on October 14, 2025. The filing does not state Rosenbaum’s total holdings after these sales.

Insider Trade Summary 10b5-1

Net Seller: 73,490 shares

Net Sell 2 txns

Insider Rosenbaum Michael George

Role Chief Executive Officer

Sold 73,490 shs ($10.62M)

Type	Security	Shares	Price	Value
Sale	Common Stock F3	1,200	$145.92	$175K
Sale	Common Stock F1, F2	72,290	$144.4718	$10.44M

Holdings After Transaction: Common Stock — 279,666 shares (Direct)

Footnotes (3)

1. F1. Shares sold by Issuer to cover taxes associated with settlement of Restricted Stock Units.
2. F2. The sale price reported in column 4 of Table 1 represents the average sale price of the shares sold ranging from $144.4716 to $144.4719 per share. The reporting person will provide, upon request by the Commission staff, the Issuer, or a security holder of the Issuer, full information regarding the number of shares sold at each separate price.
3. F3. Automatic sale pursuant to a 10b5-1 Trading Plan adopted by the Reporting Person on October 14, 2025.

Key Figures

Shares sold September 17, 2026: 72,290 shares Average sale price September 17, 2026: $144.4718 per share Shares sold September 21, 2026: 1,200 shares +3 more

6 metrics

Shares sold September 17, 2026 72,290 shares Sale of common stock to cover taxes from RSU settlement

Average sale price September 17, 2026 $144.4718 per share Weighted average sale price; individual trades ranged from $144.4716 to $144.4719

Shares sold September 21, 2026 1,200 shares Automatic sale of common stock under a Rule 10b5-1 Trading Plan

Sale price September 21, 2026 $145.92 per share Open-market or private sale of common stock

Total shares sold in filing 73,490 shares Combined total across both reported sales

Rule 10b5-1 Trading Plan adoption date October 14, 2025 Plan under which the 1,200-share sale on September 21, 2026 was executed

Key Terms

Restricted Stock Units, Rule 10b5-1 Trading Plan, average sale price

3 terms

Restricted Stock Units financial

"cover taxes associated with settlement of Restricted Stock Units"

Restricted stock units are a type of company reward where employees are promised shares of stock, but they only fully own these shares after meeting certain conditions, like staying with the company for a set time. They matter because they can become valuable assets and are often used to motivate employees to help the company succeed.

Rule 10b5-1 Trading Plan regulatory

"Automatic sale pursuant to a 10b5-1 Trading Plan adopted"

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.

average sale price financial

"represents the average sale price of the shares sold"

FAQ

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

What insider transactions did GWRE disclose in this Form 4?

The Form 4 reports two sales of Guidewire Software (GWRE) common stock by CEO Michael George Rosenbaum: 72,290 shares on September 17, 2026 and 1,200 shares on September 21, 2026, both classified as open-market or private sales.

How many GWRE shares did the CEO sell and at what prices?

CEO Michael George Rosenbaum reported selling a total of 73,490 GWRE shares: 72,290 shares at an average of $144.4718 per share on September 17, 2026, and 1,200 shares at $145.92 per share on September 21, 2026.

Why were 72,290 GWRE shares sold on September 17, 2026?

The 72,290-share sale on September 17, 2026, was made at an average price of $144.4718 per share and, according to the disclosure, the shares were sold by the issuer to cover taxes associated with settlement of Restricted Stock Units for the reporting person.

Was the 1,200-share GWRE sale under a Rule 10b5-1 plan?

Yes. The 1,200-share sale on September 21, 2026, at $145.92 per share is described as an automatic sale made pursuant to a Rule 10b5-1 Trading Plan adopted by the reporting person on October 14, 2025.

Does the Form 4 state the CEO’s remaining GWRE shareholdings?

No. For both reported transactions, the field for shares beneficially owned following the reported transaction is blank, so the filing does not state Michael George Rosenbaum’s total remaining holdings after these sales.

Are the reported GWRE insider transactions tied to compensation events?

Yes in part. The sale of 72,290 shares on September 17, 2026 was explicitly described as to cover taxes associated with settlement of Restricted Stock Units, linking that transaction to an equity compensation event.

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

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Available on EDGAR 09/21/2026 - 05:23 PM Accepted by SEC EDGAR 09/21/2026 - 05:22 PM 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)
09/17/2026

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	09/17/2026		S(1)		72,290	D	$144.4718(2)	280,866	D
Common Stock	09/21/2026		S(3)		1,200	D	$145.92	279,666	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. Shares sold by Issuer to cover taxes associated with settlement of Restricted Stock Units.

2. The sale price reported in column 4 of Table 1 represents the average sale price of the shares sold ranging from $144.4716 to $144.4719 per share. The reporting person will provide, upon request by the Commission staff, the Issuer, or a security holder of the Issuer, full information regarding the number of shares sold at each separate price.

3. 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	09/21/2026
	** 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)