Guidewire officer plans $1.4M stock sale

Guidewire Software, Inc. (GWRE) is the issuer of common stock for which officer Jeffrey Cooper has filed a notice under Rule 144 to sell 9,941 shares through Morgan Stanley Smith Barney LLC.

Rhea-AI Filing Summary

Guidewire Software, Inc. (GWRE) is the issuer of common stock for which officer Jeffrey Cooper has filed a notice under Rule 144 to sell 9,941 shares through Morgan Stanley Smith Barney LLC. The filing lists an aggregate market value of $1,417,731.74 for these shares and 81,992,669 shares outstanding as of the notice date.

The shares to be sold are tied to 8,722 performance shares and 1,219 restricted stock shares that became eligible on September 15, 2026. Over the prior three months, Cooper reported additional sales of 23,234 shares on September 17, 2026 for $3,356,658.82 and 1,348 shares on June 22, 2026 for $142,443.16.

Key Figures

Shares to be sold under Rule 144: 9,941 shares Aggregate market value of shares to be sold: $1,417,731.74 Shares outstanding: 81,992,669 shares +5 more

8 metrics

Shares to be sold under Rule 144 9,941 shares Common stock sale planned through Morgan Stanley Smith Barney LLC

Aggregate market value of shares to be sold $1,417,731.74 Value of 9,941 GWRE shares covered by the Rule 144 notice

Shares outstanding 81,992,669 shares GWRE common stock outstanding as referenced in the notice

Performance shares related to sale 8,722 shares Performance shares dated September 15, 2026

Restricted stock related to sale 1,219 shares Restricted stock dated September 15, 2026

Shares sold September 17, 2026 23,234 shares Past three months sales by Jeffrey Cooper

Proceeds from September 17, 2026 sale $3,356,658.82 Value of 23,234 GWRE shares sold

Proceeds from June 22, 2026 sale $142,443.16 Value of 1,348 GWRE shares sold

Key Terms

Rule 144, Performance Shares, Restricted Stock, Aggregate market value

4 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.

Performance Shares financial

"Common | 09/15/2026 | Performance Shares | ISSUER"

Performance shares are a type of company stock given to executives or employees that only become theirs if the company meets specific goals, like hitting certain profits or growth targets. They motivate leaders to work toward the company’s success, because their additional shares depend on achieving these results.

Restricted Stock financial

"Common | 09/15/2026 | Restricted Stock | ISSUER"

Shares granted to an individual that carry limits on transfer or sale until certain conditions are met, such as staying with the company for a set time or hitting performance targets. Think of them as a locked gift that gradually opens; for investors they matter because they affect how many shares may enter the market later, signal management incentives and potential dilution, and reveal confidence in future company performance.

Aggregate market value financial

"9941 | 1417731.74 | 81992669 | 09/18/2026"

Aggregate market value is the combined price you would pay to buy all outstanding shares of a company or all companies in a group at current market prices — essentially the sum of each stock’s market capitalization. It matters to investors because it shows the overall size and weight of an investment or sector (like the total cost to buy every piece of a puzzle), helps compare scale across companies or markets, and influences index composition and risk exposure.

FAQ

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

What does the Form 144 filing disclose for Guidewire Software, Inc. (GWRE)?

It discloses that officer Jeffrey Cooper has filed a Rule 144 notice to sell 9,941 shares of GWRE common stock, with an aggregate market value of $1,417,731.74, using Morgan Stanley Smith Barney LLC as broker.

How many Guidewire (GWRE) shares is Jeffrey Cooper planning to sell under this Form 144?

Jeffrey Cooper is planning to sell 9,941 shares of Guidewire Software common stock. The filing states an aggregate market value of $1,417,731.74 for these shares and lists 81,992,669 shares outstanding for the company.

What recent GWRE share sales by Jeffrey Cooper are reported in the last three months?

The notice reports sales of 23,234 shares of GWRE common stock on September 17, 2026 for $3,356,658.82, and 1,348 shares on June 22, 2026 for $142,443.16.

What types of equity awards are associated with the GWRE shares to be sold?

The shares to be sold are associated with Performance Shares and Restricted Stock. The filing lists 8,722 performance shares and 1,219 restricted stock shares with an acquisition date of September 15, 2026.

When are the planned GWRE share sales expected to occur?

The filing lists an approximate sale date of September 18, 2026 for the 9,941 shares to be sold under Rule 144, with trading indicated on the NYSE.

How many Guidewire (GWRE) shares are stated as outstanding in this notice?

The notice states that 81,992,669 shares of Guidewire Software common stock were outstanding. This figure is provided as context for the Rule 144 sale amount.

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

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Available on EDGAR 09/18/2026 - 04:11 PM Accepted by SEC EDGAR 09/18/2026 - 04:11 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 Place, Suite 200 San Mateo CALIFORNIA 94403
Phone	(650) 357-9100
Name of Person for Whose Account the Securities are To Be Sold	JEFFREY 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	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	Morgan Stanley Smith Barney LLC Executive Financial Services 1 New York Plaza 8th Floor New York NY 10004	9941	1417731.74	81992669	09/18/2026	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	Performance Shares	ISSUER			8722	09/15/2026	Not Applicable
Common	09/15/2026	Restricted Stock	ISSUER			1219	09/15/2026	Not Applicable

* 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 COOPER 970 Park Place, Suite 200 San Mateo CA 94403	Common	09/17/2026	23234	3356658.82
JEFFREY COOPER 970 Park Place, Suite 200 San Mateo CA 94403	Common	06/22/2026	1348	142443.16

144: Remarks and Signature

Remarks
Date of Notice	09/18/2026
Date of Plan Adoption or Giving of Instruction, If Relying on Rule 10b5-1	03/20/2026
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)