Guidewire Software Inc SEC Filings

Reporting person: James Winston King, Chief Administrative Officer and General Counsel of Guidewire Software, Inc. (GWRE).

On 09/18/2025 the reporting person executed a series of automatic sales under a 10b5-1 trading plan adopted October 15, 2024 and amended April 14, 2025. Four separate sale entries show dispositions of 1,878, 1,197, 1,940 and 2,147 shares, a total of 7,162 shares sold. Reported average sale prices for the blocks ranged approximately from $246.58 to $250.505 per share as described in the explanatory footnotes. The Form 4 shows the reporting person’s beneficial holdings declining across the transactions from 43,899 shares to 38,615 shares following the last sale. The Form is signed and dated 09/22/2025.

David Franklin Peterson, Chief Accounting Officer of Guidewire Software, sold 1,000 shares of Guidewire common stock on 09/18/2025 at a price of $249.86 per share. The filing states the sale was an automatic sale pursuant to a 10b5-1 trading plan adopted October 15, 2024. After the transaction, the reporting person beneficially owned 13,164 shares of the company's common stock as a direct holding. The Form 4 was submitted indicating the transaction and was signed by an attorney-in-fact on 09/22/2025. No options or derivative transactions are reported in this filing.

Michael George Rosenbaum, Guidewire Software, Inc. (GWRE) Chief Executive Officer and Director, reported an automatic sale of 1,400 shares of the company's common stock on 09/22/2025 at a price of $244.55 per share. The filing states the sale was made pursuant to a 10b5-1 trading plan adopted by the reporting person on October 15, 2024. After the reported transaction, Rosenbaum beneficially owns 263,558 shares of Guidewire common stock. The Form 4 was signed by an attorney-in-fact on behalf of Rosenbaum.

Guidewire Software, Inc. (GWRE) filed a Form 144 notifying of a proposed sale of 1,400 common shares through Morgan Stanley Smith Barney (NYSE) with an aggregate market value of $342,370 and an approximate sale date of 09/22/2025. The filing shows those 1,400 shares were acquired as 735 performance shares on 06/15/2022 and 665 restricted shares on 03/15/2022, matching a total of 1,400 shares available for sale. The notice also lists prior open-market sales by Mike Rosenbaum totaling 48,517 shares across dates from 06/23/2025 to 09/16/2025 with gross proceeds shown for each transaction.

Guidewire Software, Inc. (GWRE) Form 144 notice shows a proposed insider sale of 7,162 common shares, filed for sale on 09/18/2025 through Morgan Stanley Smith Barney LLC with an aggregate market value of $1,782,059.15. The filing lists the number of shares outstanding as 84,530,578. The securities to be sold include restricted stock and performance shares acquired on 09/15/2025 and 09/15/2024 (amounts: 1,371, 799, and 4,992 respectively). The document also discloses prior sales by the same person, James W. King, totaling 10,430 shares sold across 07/14/2025, 08/18/2025, and 09/16/2025 with gross proceeds listed for each transaction. The filer attests there is no undisclosed material adverse information and the notice contains customary Rule 144 representations.

Guidewire Software, Inc. (GWRE) notice reports a proposed sale under Rule 144 of 1,000 common shares through Morgan Stanley Smith Barney with an aggregate market value of $249,860, intended for sale on 09/18/2025 on the NYSE. The filing shows the shares were originally acquired as restricted stock and performance shares on 09/15/2023 (194 restricted, 806 performance). The filer also disclosed a separate sale of 1,811 shares on 09/16/2025 generating $439,832.92.

Form 144 filed for Guidewire Software, Inc. (GWRE) reports a proposed sale of 7,535 common shares through Morgan Stanley Smith Barney LLC, with an aggregate market value of $1,874,377.21 and approximately 84,530,578 shares outstanding.

The securities were acquired on 09/15/2025 as 1,544 restricted stock and 5,991 performance shares, with payment noted as Not Applicable. The filing also discloses a sale on 09/16/2025 by Jeffrey Cooper of 14,103 shares for gross proceeds of $3,425,148.80. The filer represents they are not aware of any undisclosed material adverse information and includes the standard signature and criminal-statement notice.

James Winston King, Chief Administrative Officer and General Counsel of Guidewire Software (GWRE), reported the receipt and partial disposition of company stock following PSU vesting. On 09/15/2025 10,597 performance shares converted into 10,597 common shares. The next day, 09/16/2025, 7,149 shares were sold at an average price of $242.867 per share to cover taxes, reducing his beneficial ownership from 52,926 to 45,777 shares. The filing explains these PSUs reflect performance determinations: Part 1 achieved 101.8% of FY23 targets (adding 123 PSUs) with staggered time-based vesting, and Part 2 achieved 120% of FY25 targets (adding 1,377 PSUs) and met time-based vesting on 09/15/2025. The PSUs underlying the award convert into common stock and have an expiration date of 09/15/2032.

David Franklin Peterson, identified as an officer (Chief Accounting Officer), reported transactions in Guidewire Software, Inc. (GWRE). On 09/15/2025 Mr. Peterson was credited with 3,179 performance shares (code M) at $0 relating to vested Performance Share Units (PSUs), increasing his beneficial ownership to 15,975 shares. On 09/16/2025 he sold 1,811 common shares to cover taxes on the RSU settlement at an average sale price of $242.8675 per share, leaving him with 14,164 shares beneficially owned.

The Form 4 notes the PSUs have an expiration/settlement reference of 09/15/2032 and explains performance determinations: Part 1 met FY23 targets at 101.8% (adding 36 PSUs) with staggered vesting; Part 2 met FY25 targets at 120% (adding 413 PSUs) and satisfied time-based vesting on 09/15/2025. The form was signed by an attorney-in-fact on 09/17/2025.