Guidewire Software: Rosenbaum plans $225K share sale

The shares are described as performance shares dated September 15, 2023, with Morgan Stanley Smith Barney LLC listed as broker.

Rhea-AI Filing Summary

Guidewire Software, Inc. (GWRE) is named in a notice reporting that Michael George Rosenbaum intends to sell 1,200 shares of common stock, with an aggregate market value of $224,628.00 and an approximate sale date of October 26, 2026. Recent sales listed include 72,290 shares on September 17, 2026, with a listed value of $10,443,869.86.

Key Figures

Proposed sale: 1,200 shares Aggregate market value of proposed sale: $224,628.00 Shares sold: 72,290 shares +1 more

4 metrics

Proposed sale 1,200 shares Common stock

Aggregate market value of proposed sale $224,628.00 Approximate sale date: October 26, 2026

Shares sold 72,290 shares September 17, 2026; listed among sales for the prior three months

Listed value of September 17 sale $10,443,869.86 September 17, 2026

Key Terms

Rule 144, Performance Shares, Securities Sold During The Past 3 Months

3 terms

Rule 144 regulatory

"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

"Performance Shares"

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.

Securities Sold During The Past 3 Months financial

"Securities Sold During The Past 3 Months"

FAQ

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

How many GWRE shares does Michael George Rosenbaum intend to sell?

Michael George Rosenbaum intends to sell 1,200 shares of common stock, with an aggregate market value of $224,628.00. The approximate sale date is October 26, 2026, and Morgan Stanley Smith Barney LLC is listed as broker.

What recent GWRE stock sale is listed for September 17, 2026?

The listed transaction was a sale of 72,290 shares on September 17, 2026, with a listed value of $10,443,869.86. It appears among the sales reported for the prior three months.

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

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Available on EDGAR 10/26/2026 - 04:26 PM EDT Accepted by SEC EDGAR 10/26/2026 - 04:26 PM EDT 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	0001784996
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	MIKE ROSENBAUM
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
Relationship to Issuer	Director

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	1200	224628.00	81992669	10/26/2026	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	09/15/2023	Performance Shares	ISSUER			1200	09/15/2023	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
MIKE ROSENBAUM 970 Park Place, Suite 200 San Mateo CA 94403	Common	10/19/2026	1200	201480.00
MIKE ROSENBAUM 970 Park Place, Suite 200 San Mateo CA 94403	Common	10/12/2026	1200	202764.00
MIKE ROSENBAUM 970 Park Place, Suite 200 San Mateo CA 94403	Common	10/05/2026	1200	183024.00
MIKE ROSENBAUM 970 Park Place, Suite 200 San Mateo CA 94403	Common	09/28/2026	1200	171180.00
MIKE ROSENBAUM 970 Park Place, Suite 200 San Mateo CA 94403	Common	09/21/2026	1200	175104.00
MIKE ROSENBAUM 970 Park Place, Suite 200 San Mateo CA 94403	Common	09/17/2026	72290	10443869.86
MIKE ROSENBAUM 970 Park Place, Suite 200 San Mateo CA 94403	Common	09/14/2026	1200	175044.00
MIKE ROSENBAUM 970 Park Place, Suite 200 San Mateo CA 94403	Common	09/08/2026	1200	192624.00
MIKE ROSENBAUM 970 Park Place, Suite 200 San Mateo CA 94403	Common	08/31/2026	1200	245328.00
MIKE ROSENBAUM 970 Park Place, Suite 200 San Mateo CA 94403	Common	08/24/2026	1200	225384.00
MIKE ROSENBAUM 970 Park Place, Suite 200 San Mateo CA 94403	Common	08/17/2026	1200	207456.00
MIKE ROSENBAUM 970 Park Place, Suite 200 San Mateo CA 94403	Common	08/10/2026	1200	203400.00
MIKE ROSENBAUM 970 Park Place, Suite 200 San Mateo CA 94403	Common	08/03/2026	1200	187104.00
MIKE ROSENBAUM 970 Park Place, Suite 200 San Mateo CA 94403	Common	07/27/2026	1200	170772.00

144: Remarks and Signature

Remarks
Date of Notice	10/26/2026
Date of Plan Adoption or Giving of Instruction, If Relying on Rule 10b5-1	10/14/2025
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/ Michael George Rosenbaum
ATTENTION: Intentional misstatements or omission of facts constitute Federal Criminal Violations (See 18 U.S.C. 1001)