[144] GUIDEWIRE SOFTWARE, INC. SEC Filing

Rhea-AI Filing Summary

Form 144 filed for GUIDEWIRE SOFTWARE, INC. (GWRE) reporting proposed and recent sales of common stock by Mike Rosenbaum. The notice lists a proposed sale of 1,400 shares through Morgan Stanley Smith Barney with an aggregate market value of $365,792 and shows 84,195,223 shares outstanding. The securities to be sold were acquired as restricted stock on 03/15/2022. The filing also discloses multiple recent sales by the same person between 06/09/2025 and 09/02/2025, including a larger sale of 5,925 shares on 06/17/2025 for $1,474,957.84. The filer certifies no undisclosed material adverse information and provides broker and address details for the transaction.

Positive

• Full disclosure of proposed and recent sales including share counts, gross proceeds, broker, and acquisition details
• Acquisition date and nature (restricted stock acquired 03/15/2022) are explicitly stated
• Large recent sale of 5,925 shares on 06/17/2025 with gross proceeds of $1,474,957.84 is disclosed

Negative

• Frequent insider sales are documented across multiple dates from 06/09/2025 to 09/02/2025, which may be notable to investors
• No information in this filing about any 10b5-1 plan adoption date or whether sales are pursuant to such a plan

Insights

Financial Analyst

TL;DR: Routine insider sale disclosures show steady monetization of restricted shares without additional company financial data.

The filing documents a proposed sale of 1,400 GWRE shares and a series of recent sales by Mike Rosenbaum, including a 5,925-share sale generating $1,474,957.84. These are reported under Rule 144 and identify the broker and acquisition details (restricted stock dated 03/15/2022). From an analyst perspective, this is a standard liquidity event for an insider and provides transparency about share dispositions but contains no operating results, guidance, or events that alter company fundamentals.

Corporate Governance Expert

TL;DR: Disclosure complies with Rule 144 requirements; shows multiple insider sales across recent months.

The submission lists the required seller attestations and broker information, and it affirms the signer does not possess undisclosed material adverse information. The record of frequent sales over several months is fully itemized by date, share count, and gross proceeds, supporting transparent personal trading activity. The filing does not indicate any trading plan adoption date or 10b5-1 plan specifics within the provided content.

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

144: Issuer Information

Name of Issuer

SEC File Number

Address of Issuer

Phone

Name of Person for Whose Account the Securities are To Be Sold

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

Relationship to Issuer

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	365792.00	84195223	09/08/2025	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	03/15/2022	Restricted Stock	ISSUER			1400	03/15/2022	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	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
MIKE ROSENBAUM 970 Park Place, Suite 200 San Mateo CA 94403	Common	07/21/2025	1400	311234.00
MIKE ROSENBAUM 970 Park Place, Suite 200 San Mateo CA 94403	Common	07/14/2025	1400	308910.00
MIKE ROSENBAUM 970 Park Place, Suite 200 San Mateo CA 94403	Common	07/07/2025	1400	322980.00
MIKE ROSENBAUM 970 Park Place, Suite 200 San Mateo CA 94403	Common	06/30/2025	1400	331646.00
MIKE ROSENBAUM 970 Park Place, Suite 200 San Mateo CA 94403	Common	06/23/2025	1400	333368.00
MIKE ROSENBAUM 970 Park Place, Suite 200 San Mateo CA 94403	Common	06/17/2025	5925	1474957.84
MIKE ROSENBAUM 970 Park Place, Suite 200 San Mateo CA 94403	Common	06/16/2025	1400	356342.00
MIKE ROSENBAUM 970 Park Place, Suite 200 San Mateo CA 94403	Common	06/09/2025	1400	359100.00

144: Remarks and Signature

Remarks

Date of Notice

Date of Plan Adoption or Giving of Instruction, If Relying on Rule 10b5-1

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

ATTENTION: Intentional misstatements or omission of facts constitute Federal Criminal Violations (See 18 U.S.C. 1001)

FAQ

Who is the seller in the GWRE Form 144 filing?

The seller is Mike Rosenbaum, with address listed as 970 Park Place, Suite 200, San Mateo, CA 94403.

How many shares does the Form 144 propose to sell and through which broker?

The notice proposes sale of 1,400 common shares through Morgan Stanley Smith Barney LLC.

What is the aggregate market value and outstanding shares reported?

Aggregate market value is reported as $365,792.00 for the proposed sale and the filing lists 84,195,223 shares outstanding.

When were the securities to be sold originally acquired?

The securities were acquired as restricted stock on 03/15/2022 and the amount to be sold is 1,400 shares.

Has the filer sold other GWRE shares recently?

Yes. The filing lists multiple sales between 06/09/2025 and 09/02/2025, including a sale of 5,925 shares on 06/17/2025 for $1,474,957.84.