GWRE Form 144: Mike Rosenbaum to sell 1,400 shares on NYSE

GWRE insider Mike Rosenbaum filed a Form 144 notice to sell 1,400 shares of common stock through Morgan Stanley Smith Barney LLC Executive Financial Services.

Rhea-AI Filing Summary

GWRE insider Mike Rosenbaum filed a Form 144 notice to sell 1,400 shares of common stock through Morgan Stanley Smith Barney LLC Executive Financial Services. The filing lists an aggregate market value of $357,560.00, an approximate sale date of 10/27/2025, and trading on the NYSE. Shares outstanding were 84,530,578.

The shares to be sold were acquired as performance shares on 09/15/2022 from the issuer. The notice also details recent activity: multiple 1,400‑share sales in the past three months and a larger sale of 30,317 shares on 09/16/2025 for $7,362,962.35, along with other transactions on dates including 09/02/2025, 09/29/2025, and 10/20/2025.

FAQ

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

What does GWRE’s Form 144 filing disclose?

A planned sale of 1,400 common shares with an aggregate market value of $357,560.00, to be sold on or about 10/27/2025 on the NYSE.

Who is the selling security holder in GWRE’s Form 144?

The seller is Mike Rosenbaum, as listed in the notice.

Which broker is handling the GWRE share sale?

The filing names Morgan Stanley Smith Barney LLC Executive Financial Services as broker.

How many GWRE shares are outstanding?

Shares outstanding were 84,530,578.

How were the shares to be sold acquired?

They were acquired as performance shares on 09/15/2022 from the issuer.

What recent GWRE insider sales are listed?

Sales include multiple 1,400‑share transactions and a 30,317‑share sale on 09/16/2025 for $7,362,962.35.

On which exchange will the shares be sold?

The filing lists the NYSE as the exchange.

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

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Accepted by SEC EDGAR 10/27/2025 - 04:00 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	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	1400	357560.00	84530578	10/27/2025	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	09/15/2022	Performance Shares	ISSUER			1400	09/15/2022	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	10/20/2025	1400	343980.00
MIKE ROSENBAUM 970 Park Place, Suite 200 San Mateo CA 94403	Common	10/13/2025	1400	335594.00
MIKE ROSENBAUM 970 Park Place, Suite 200 San Mateo CA 94403	Common	10/06/2025	1400	322112.00
MIKE ROSENBAUM 970 Park Place, Suite 200 San Mateo CA 94403	Common	09/29/2025	1400	325150.00
MIKE ROSENBAUM 970 Park Place, Suite 200 San Mateo CA 94403	Common	09/22/2025	1400	342370.00
MIKE ROSENBAUM 970 Park Place, Suite 200 San Mateo CA 94403	Common	09/16/2025	30317	7362962.35
MIKE ROSENBAUM 970 Park Place, Suite 200 San Mateo CA 94403	Common	09/15/2025	1400	353962.00
MIKE ROSENBAUM 970 Park Place, Suite 200 San Mateo CA 94403	Common	09/08/2025	1400	365792.00
MIKE ROSENBAUM 970 Park Place, Suite 200 San Mateo CA 94403	Common	09/02/2025	1400	300020.00
MIKE ROSENBAUM 970 Park Place, Suite 200 San Mateo CA 94403	Common	08/25/2025	1400	300580.00
MIKE ROSENBAUM 970 Park Place, Suite 200 San Mateo CA 94403	Common	08/18/2025	1400	296254.00
MIKE ROSENBAUM 970 Park Place, Suite 200 San Mateo CA 94403	Common	08/11/2025	1400	297416.00
MIKE ROSENBAUM 970 Park Place, Suite 200 San Mateo CA 94403	Common	08/04/2025	1400	315056.00
MIKE ROSENBAUM 970 Park Place, Suite 200 San Mateo CA 94403	Common	07/28/2025	1400	313250.00

144: Remarks and Signature

Remarks
Date of Notice	10/27/2025
Date of Plan Adoption or Giving of Instruction, If Relying on Rule 10b5-1	10/15/2024
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)