Guidewire CFO may sell $3.4M in stock for taxes

Guidewire’s CFO filed a Rule 144 notice to sell shares tied to September 2026 RSU and PSU vesting, mainly for tax withholding.

Rhea-AI Filing Summary

Guidewire Software, Inc. (GWRE) was notified that its Chief Financial Officer, Jeffrey Elliott Cooper, has filed a Form 144 indicating an intent to sell up to 23,234 shares of Common Stock under Rule 144. The planned sale has an aggregate market value of $3,356,657.73, with 81,992,669 shares outstanding. The shares relate to RSU and PSU awards vesting on September 15, 2026, and the notice states that the amounts listed reflect automatic sell-to-cover transactions to satisfy tax withholding obligations under the company’s Amended and Restated 2020 Stock Plan.

Key Figures

Shares to be sold under Rule 144: 23,234 shares Aggregate market value of planned sale: $3,356,657.73 Shares outstanding: 81,992,669 shares +4 more

7 metrics

Shares to be sold under Rule 144 23,234 shares Maximum number of Guidewire Common Stock shares indicated in the Form 144

Aggregate market value of planned sale $3,356,657.73 Value corresponding to the 23,234 shares of Common Stock

Shares outstanding 81,992,669 shares Guidewire Common Stock shares outstanding as stated in the notice

Prior 3-month sale volume 1,348 shares Common Stock sold on June 22, 2026

Prior 3-month sale value $142,443.16 Aggregate value of 1,348 shares sold on June 22, 2026

RSU tranche example 1,721 shares Common Stock from RSU vesting granted September 15, 2022, vesting September 15, 2026

PSU tranche example 37,826 shares Common Stock from PSU vesting granted September 13, 2023, vesting September 15, 2026

Key Terms

Rule 144, sell-to-cover, Restricted Stock Unit (RSU), Performance Stock Unit (PSU), +1 more

5 terms

Rule 144 regulatory

"See the definition of "person" in paragraph (a) of Rule 144."

Rule 144 is a U.S. securities regulation that sets conditions under which restricted or insider-held shares can be legally resold to the public, such as required holding periods, availability of public information, limits on how much can be sold at once, and certain filing requirements. For investors it matters because it determines when previously locked-up shares can enter the market — like a release valve that can increase supply, affect share price, and signal insider intent.

sell-to-cover financial

"reflect automatic sell-to-cover transactions to satisfy tax withholding obligations"

Sell-to-cover is when part of newly issued or exercised company stock is immediately sold to pay required taxes and fees, so the recipient keeps the remaining shares. For investors this matters because it reduces the number of shares insiders or employees actually hold after a grant, can create small, routine share sales that aren’t signal of cashing out, and slightly increases share supply on the market—like selling a portion of a paycheck to cover the tax bill.

Restricted Stock Unit (RSU) financial

"Vesting of RSU (Grant Date: 09/15/2022)"

A restricted stock unit (RSU) is a promise from a company to give an employee company shares (or cash equal to their value) at a future date if certain conditions are met, such as staying with the company or hitting performance targets. For investors, RSUs matter because when they convert into actual shares they increase the number of shares available and can create selling pressure as employees cash out—think of them as a future paycheck paid in company stock.

Performance Stock Unit (PSU) financial

"Vesting of PSU (Grant Date: 09/13/2023)"

Amended and Restated 2020 Stock Plan financial

"under the Issuer's Amended and Restated 2020 Stock Plan"

FAQ

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

What does the Form 144 filed for GWRE disclose about planned share sales?

The Form 144 reports that Guidewire’s CFO, Jeffrey Elliott Cooper, may sell up to 23,234 shares of Guidewire Software, Inc. Common Stock under Rule 144, with an aggregate market value of $3,356,657.73, based on current market prices and share data in the notice.

How many GWRE shares are outstanding according to this Form 144?

The notice states that 81,992,669 shares of Guidewire Software, Inc. Common Stock are outstanding. This figure provides context for the planned sale amount and comes from the securities information section of the filing.

What is the purpose of the GWRE CFO’s planned share sales in this Form 144?

According to the remarks, the listed share amounts reflect automatic sell-to-cover transactions to satisfy tax withholding obligations under Guidewire’s Amended and Restated 2020 Stock Plan, representing a portion of RSU and PSU vesting on September 15, 2026.

Which equity awards for GWRE’s CFO are linked to this Form 144?

The securities to be sold are Common Stock acquired upon vesting of RSUs and PSUs granted on September 15, 2022 and September 13, 2023, and RSUs granted on September 11, 2024 and September 11, 2025, all vesting on September 15, 2026.

Has the GWRE CFO sold shares in the last three months before this Form 144?

Yes. The Form 144 lists a prior sale of 1,348 shares of Common Stock on June 22, 2026 for an aggregate value of $142,443.16, reported under securities sold during the past three months.

Through which broker may the GWRE CFO execute the planned Form 144 sales?

The notice identifies Morgan Stanley Smith Barney LLC Executive Financial Services, at 1 New York Plaza, New York, as the broker for the potential sale of Guidewire Software, Inc. Common Stock.

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

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Available on EDGAR 09/17/2026 - 06:48 PM Accepted by SEC EDGAR 09/17/2026 - 06:47 PM Learn about SEC filing dates

Form 144 Filer Information	UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Form 144 NOTICE OF PROPOSED SALE OF SECURITIES PURSUANT TO RULE 144 UNDER THE SECURITIES ACT OF 1933
FORM 144

144: Filer Information

Filer CIK	0001805719
Filer CCC	XXXXXXXX
Is this a LIVE or TEST Filing?	LIVE TEST
Submission Contact Information
Name
Phone
E-Mail Address

144: Issuer Information

Name of Issuer	Guidewire Software, Inc.
SEC File Number	001-35394
Address of Issuer	970 Park Pl, Suite 200 San Mateo CALIFORNIA 94403
Phone	650-357-9100
Name of Person for Whose Account the Securities are To Be Sold	Jeffrey Elliott Cooper
See the definition of "person" in paragraph (a) of Rule 144. Information is to be given not only as to the person for whose account the securities are to be sold but also as to all other persons included in that definition. In addition, information shall be given as to sales by all persons whose sales are required by paragraph (e) of Rule 144 to be aggregated with sales for the account of the person filing this notice.
Relationship to Issuer	Chief Financial Officer

144: Securities Information

Title of the Class of Securities To Be Sold	Name and Address of the Broker	Number of Shares or Other Units To Be Sold	Aggregate Market Value	Number of Shares or Other Units Outstanding	Approximate Date of Sale	Name the Securities Exchange
Common Stock	Morgan Stanley Smith Barney LLC Executive Financial Services 1 New York Plaza 38th Floor New York NY 10004	23234	3356657.73	81992669	09/17/2026	NYSE

Furnish the following information with respect to the acquisition of the securities to be sold and with respect to the payment of all or any part of the purchase price or other consideration therefor:

144: Securities To Be Sold

Title of the Class	Date you Acquired	Nature of Acquisition Transaction	Name of Person from Whom Acquired	Is this a Gift?	Date Donor Acquired	Amount of Securities Acquired	Date of Payment	Nature of Payment *
Common	09/15/2026	Vesting of RSU (Grant Date: 09/15/2022)	Issuer			1721	09/15/2026	N/A (acquired as compensation)
Common	09/15/2026	Vesting of PSU (Grant Date: 09/13/2023)	Issuer			37826	09/15/2026	N/A (acquired as compensation)
Common	09/15/2026	Vesting of RSU (Grant Date: 09/13/2023)	Issuer			1738	09/15/2026	N/A (acquired as compensation)
Common	09/15/2026	Vesting of RSU (Grant Date: 09/11/2024)	Issuer			1038	09/15/2026	N/A (acquired as compensation)
Common	09/15/2026	Vesting of RSU (Grant Date: 09/11/2025)	Issuer			790	09/15/2026	N/A (acquired as compensation)

* If the securities were purchased and full payment therefor was not made in cash at the time of purchase, explain in the table or in a note thereto the nature of the consideration given. If the consideration consisted of any note or other obligation, or if payment was made in installments describe the arrangement and state when the note or other obligation was discharged in full or the last installment paid.

Furnish the following information as to all securities of the issuer sold during the past 3 months by the person for whose account the securities are to be sold.

144: Securities Sold During The Past 3 Months

Name and Address of Seller	Title of Securities Sold	Date of Sale	Amount of Securities Sold	Gross Proceeds
Jeffrey Elliott Cooper c/o Guidewire Software, Inc. 970 Park Pl, Suite 200 San Mateo CA 94403	Common Stock	06/22/2026	1348	142443.16

144: Remarks and Signature

Remarks	The amounts listed under 'Number of Shares to be Sold' reflect automatic sell-to-cover transactions to satisfy tax withholding obligations under the Issuer's Amended and Restated 2020 Stock Plan, representing a portion of the full RSU and PSU vests on September 15, 2026.
Date of Notice	09/17/2026
ATTENTION:
The person for whose account the securities to which this notice relates are to be sold hereby represents by signing this notice that he does not know any material adverse information in regard to the current and prospective operations of the Issuer of the securities to be sold which has not been publicly disclosed. If such person has adopted a written trading plan or given trading instructions to satisfy Rule 10b5-1 under the Exchange Act, by signing the form and indicating the date that the plan was adopted or the instruction given, that person makes such representation as of the plan adoption or instruction date.
Signature	/s/ Jeffrey Elliott Cooper
ATTENTION: Intentional misstatements or omission of facts constitute Federal Criminal Violations (See 18 U.S.C. 1001)