Guidewire Software Inc Form 4 Filings

Guidewire Software CEO Michael George Rosenbaum, who also serves as a director, reported an automatic sale of company common stock. On January 13, 2026, he sold 1,200 shares of Guidewire common stock at a price of $180.87 per share in an open market transaction coded as a sale. The transaction was carried out under a Rule 10b5-1 trading plan that he adopted on October 14, 2025, which means the trades were pre-arranged rather than made at his discretion on the trade date. After this sale, Rosenbaum beneficially owns 236,743 shares of Guidewire common stock directly.

Guidewire Software, Inc. Chief Executive Officer and Director Michael George Rosenbaum reported a sale of company stock. On 12/29/2025, he sold 1,400 shares of common stock at a price of $204.95 per share in a transaction coded "S" for sale. After this transaction, he beneficially owned 237,943 shares of Guidewire common stock in direct ownership.

The filing notes that this was an automatic sale made under a Rule 10b5-1 trading plan that Rosenbaum adopted on October 15, 2024, which is a pre-arranged plan designed to allow insiders to sell shares over time according to set instructions.

Guidewire Software, Inc. Chief Executive Officer and director Michael George Rosenbaum sold 1,400 shares of common stock on December 22, 2025 at $200.72 per share. Following this transaction, he beneficially owned 239,343 shares directly. The sale was described as an automatic transaction carried out under a Rule 10b5-1 trading plan that he adopted on October 15, 2024, which allows preset, scheduled sales of company stock by insiders.

Guidewire Software, Inc. reported that officer James Winston King, Chief Admin Officer and General Counsel, disposed of company common stock in two transactions. On 12/16/2025, 1,457 shares of common stock were sold at an average price of $192.0761 per share, and on 12/18/2025, 1,860 shares were sold at $195 per share.

After these transactions, King beneficially owns 33,702 shares of Guidewire common stock directly. The filing explains that the first transaction reflects shares sold by the issuer to cover taxes associated with the settlement of restricted stock units, and the second transaction was an automatic sale made under a Rule 10b5-1 trading plan adopted on October 15, 2024 and amended on April 14, 2025.

Guidewire Software, Inc. chief financial officer Jeffrey Elliott Cooper reported two sales of the company’s common stock in December 2025. On December 16, 2025, 2,872 shares of common stock were sold at $192.0761 per share, leaving him with 74,201 shares directly owned. On December 18, 2025, a further 1,232 shares were sold at $195 per share, bringing his direct holdings to 72,969 shares.

The disclosure states that the first transaction reflects shares sold by the issuer to cover taxes associated with the settlement of restricted stock units, and that the second transaction was an automatic sale pursuant to a 10b5-1 Trading Plan adopted by the reporting person on October 15, 2024.

Guidewire Software, Inc. Chief Executive Officer and director Michael George Rosenbaum reported a sale of 6,015 shares of common stock on 12/16/2025. The shares were sold at a price of $192.0761 per share, according to the transaction details.

The filing notes that the shares were sold by the issuer to cover taxes associated with the settlement of Restricted Stock Units. After this transaction, Rosenbaum directly beneficially owns 240,743 shares of Guidewire common stock.

Guidewire Software, Inc. reported an insider stock transaction by its chief accounting officer, David Franklin Peterson. On 12/16/2025, 358 shares of Guidewire common stock were sold at $192.0761 per share. The explanation states that the shares were sold by the issuer to cover taxes associated with the settlement of restricted stock units. After this tax-related sale, Peterson beneficially owns 12,806 shares of Guidewire common stock directly.

Guidewire Software president John P. Mullen reported a tax-related transaction in company stock. On 12/16/2025, 7,975 shares of Guidewire common stock were sold at $192.0761 per share.

The explanation states that the issuer sold these shares to cover taxes associated with the settlement of restricted stock units. After this transaction, Mullen directly beneficially owned 141,983 shares of Guidewire common stock.

Guidewire Software director Mark V. Anquillare reported an equity grant from the company. On December 15, 2025, he received 1,196 restricted stock units relating to common stock at a reported price of $0, increasing his directly held amount to 2,716 shares after the transaction. The award is scheduled to become fully vested after the earlier of one year from the grant date or Guidewire Software’s next annual meeting of stockholders.

Guidewire Software, Inc. reported that a director acquired 1,196 restricted stock units of its common stock on December 15, 2025 at a price of $0 per unit.

After this grant, the reporting person beneficially owned 2,371 shares. These restricted stock units are scheduled to become 100% vested after the earlier of one year from the grant date or Guidewire Software’s next annual meeting of stockholders.

Guidewire Software director Rajani Ramanathan received a grant of 1,196 restricted stock units of common stock on December 15, 2025. These units are scheduled to vest 100% after the earlier of one year from the grant date or the company’s next annual meeting of stockholders. Following this grant, she beneficially owns 11,057 shares of Guidewire common stock.

Guidewire Software, Inc. director David S. Bauer received a new equity grant in the form of restricted stock units. On 12/15/2025, he was awarded 1,196 restricted stock units of common stock at a stated price of $0, reported as an acquisition under code "A." Following this grant, he beneficially owned 7,099 shares of common stock, held directly.

The restricted stock units were granted on December 15, 2025 and are scheduled to become 100% vested after the earlier of one year from the grant date or the issuer's next annual meeting of stockholders. This filing reflects equity-based compensation to a board member rather than an open-market purchase or sale.

Guidewire Software, Inc. director Michael C. Keller reported a stock-based compensation grant. On December 15, 2025, he received 1,196 restricted stock units of Guidewire common stock at a stated price of $0, reflecting a typical equity award rather than a cash purchase.

After this grant, Keller beneficially owns 10,606 shares of Guidewire common stock in direct form. The restricted stock units are scheduled to become 100% vested after the earlier of one year from the grant date or the company’s next annual meeting of stockholders, tying his compensation to the company’s long-term performance and governance cycle.

Guidewire Software director Catherine P. Lego reported a new equity award and updated her holdings. On December 15, 2025 she received 1,196 restricted stock units representing common stock, granted at a price of $0. Following this award she beneficially owns 14,393 shares of common stock directly, in addition to 2,000 shares held indirectly through the Catherine Pierson Lego Trust UA DTD 05/09/07, where she is the sole trustee and beneficiary. The restricted stock units are scheduled to vest 100% after the earlier of one year from the grant date or the issuer's next annual meeting of stockholders.

Guidewire Software director Margaret Dillon reported an equity award of the company’s common stock. On December 15, 2025, she acquired 1,196 shares of Guidewire common stock in the form of restricted stock units at a stated price of $0 per share. Following this transaction, she beneficially owns 16,393 shares of Guidewire common stock directly.

According to the footnote, these restricted stock units were granted on December 15, 2025 and are scheduled to become 100% vested after the earlier of one year from the grant date or the issuer’s next annual meeting of stockholders. The report relates to a single reporting person and reflects an acquisition of restricted stock units rather than an open‑market purchase or sale.

Guidewire Software, Inc. chief executive officer and director Michael George Rosenbaum reported selling 1,400 shares of the company’s common stock on 12/15/2025 at a price of $204.34 per share. The transaction was coded as a sale and was carried out automatically under a Rule 10b5-1 trading plan that he adopted on October 15, 2024.

After this transaction, Rosenbaum directly beneficially owns 246,758 shares of Guidewire common stock. This reflects a routine insider share sale by a senior executive and does not describe any change in Guidewire’s operations or financial results.

Guidewire Software, Inc. insider trade disclosed: Guidewire Software's Chief Executive Officer and director Michael George Rosenbaum reported selling 1,400 shares of common stock on 12/08/2025 at a price of $210.87 per share. After this transaction, he beneficially owns 248,158 shares of Guidewire common stock. The sale was executed under an automatic Rule 10b5-1 trading plan that he adopted on October 15, 2024, which pre-schedules trades under set conditions.

Guidewire Software, Inc. insider transaction: A company officer and president reported selling 3,000 shares of Guidewire common stock on 12/01/2025 at a price of $213.44 per share. After this sale, the reporting person beneficially owns 149,958 shares of Guidewire common stock in direct ownership form.

The sale was an automatic transaction made under a pre-arranged Rule 10b5-1 trading plan that the reporting person adopted on October 15, 2024. Such plans are designed to allow insiders to systematically sell shares over time according to preset instructions.

Guidewire Software, Inc. insider trading report: Chief Executive Officer and Director Michael George Rosenbaum reported a sale of common stock of Guidewire Software, Inc. on 12/01/2025. He sold 1,400 shares of common stock at a price of $213.44 per share in a transaction coded "S" for sale. After this transaction, he beneficially owns 249,558 shares of Guidewire common stock in direct ownership form.

The filing notes that this was an automatic sale carried out under a Rule 10b5-1 trading plan adopted by Rosenbaum on October 15, 2024, which is designed to pre-arrange trades according to specified instructions.

Guidewire Software, Inc. (GWRE) reported an insider stock transaction by its Chief Executive Officer and director, Michael George Rosenbaum. On 11/24/2025, he sold 1,400 shares of Guidewire common stock at a price of $213.23 per share.

Following this sale, Rosenbaum beneficially owns 250,958 shares of Guidewire common stock in direct ownership. The filing notes that the sale was an automatic transaction under a Rule 10b5-1 trading plan, which was adopted on October 15, 2024, indicating it was pre-arranged under SEC rules for insider trading plans.

Guidewire Software, Inc. reported an insider share sale by its Chief Executive Officer and Director, Michael George Rosenbaum. On 11/17/2025, he sold 1,400 shares of Guidewire common stock in an open market transaction with a sale code of "S" at a price of $222.54 per share, executed under an automatic Rule 10b5-1 trading plan adopted on October 15, 2024. Following this transaction, he beneficially owns 252,358 shares of Guidewire common stock in direct ownership.

Guidewire Software, Inc. insider trade reported – An officer of Guidewire Software, Inc. (GWRE), serving as Chief Administrative Officer and General Counsel, reported a sale of common stock. On 11/17/2025, the reporting person sold 798 shares of Guidewire common stock at a price of $222.54 per share in a transaction coded "S" for sale. After this transaction, the officer beneficially owned 37,019 shares of Guidewire common stock. The sale was executed under an automatic Rule 10b5-1 trading plan that the reporting person adopted on October 15, 2024 and amended on April 14, 2025.

Guidewire Software (GWRE) CEO and director Michael George Rosenbaum sold 1,400 shares of common stock on 11/10/2025 at a price of $218.53 per share. The transaction was an automatic sale made under a Rule 10b5-1 trading plan adopted on October 15, 2024. Following the sale, he beneficially owns 253,758 shares, held directly.

Guidewire Software (GWRE): CEO and Director Michael George Rosenbaum reported a sale of 1,400 shares of common stock on 11/03/2025 at $231.85 per share. The transaction was an automatic sale under a Rule 10b5-1 trading plan adopted on October 15, 2024. Following the sale, he beneficially owns 255,158 shares, held directly.

Guidewire Software (GWRE) filed a Form 4 disclosing an insider sale. On 11/03/2025, the company’s President sold 3,000 shares of common stock at $231.85 per share under a pre‑set Rule 10b5‑1 trading plan adopted on October 15, 2024. Following the transaction, the reporting person directly beneficially owned 152,958 shares.

Guidewire Software (GWRE) reported an insider transaction by CEO and director Michael George Rosenbaum. On 10/27/2025, he sold 1,400 shares of common stock at $255.4 per share, an automatic sale under a Rule 10b5-1 trading plan adopted on 10/15/2024. Following the sale, he beneficially owns 256,558 shares directly.

Guidewire Software (GWRE) reported an insider transaction by its Chief Executive Officer and Director, Michael George Rosenbaum. On 10/20/2025, he sold 1,400 shares of common stock at a reported $245.70 per share under a pre‑arranged Rule 10b5‑1 trading plan adopted on October 15, 2024.

Following this sale, Rosenbaum beneficially owns 257,958 shares, held directly. The filing indicates this was an automatic sale pursuant to the trading plan.

Guidewire Software (GWRE) reported an insider transaction by its Chief Administrative Officer and General Counsel. On 10/20/2025, the officer sold 798 shares of common stock at $245.7 per share, reported under transaction code S.

Following the sale, the officer beneficially owns 37,817 shares, held directly. The filing notes the sale was an automatic transaction made pursuant to a Rule 10b5-1 trading plan adopted on October 15, 2024 and amended on April 14, 2025.

Guidewire Software (GWRE) — Form 4: CEO and Director Michael George Rosenbaum reported a sale of common stock. On 10/13/2025, he sold 1,400 shares at $239.71 per share (Transaction Code: S). The sale was executed under a Rule 10b5-1 trading plan adopted on October 15, 2024. Following the transaction, he beneficially owns 259,358 shares, held directly.

Michael George Rosenbaum, Guidewire Software CEO and director, reported an automatic sale of 1,400 shares of Guidewire common stock on 10/06/2025 at a price of $230.08 per share. The filing shows 260,758 shares beneficially owned following the transaction. The sale was executed under a 10b5-1 trading plan that the reporting person adopted on 10/15/2024, and the Form 4 was signed by an attorney-in-fact on 10/06/2025. The filing discloses a routine insider sale using a pre-established plan rather than an ad-hoc transaction.

John P. Mullen, President of Guidewire Software (GWRE), reported a sale of company stock on 10/01/2025. The filing shows an automatic sale of 3,000 shares of Common Stock at $230.73 per share executed under a 10b5-1 trading plan adopted October 15, 2024. After the reported transaction the filing lists 155,958 shares beneficially owned by the reporting person. The Form 4 was signed by an attorney-in-fact, Winston King.

Guidewire Software director David S. Bauer executed an automatic sale of common stock under a 10b5-1 trading plan. On 10/01/2025 Mr. Bauer (reporting through counsel) sold 500 shares at a price of $230.73 per share, reducing his reported beneficial ownership to 5,903 shares. The filing identifies Mr. Bauer as a director and shows the sale was an automatic disposition under a 10b5-1 plan adopted on December 12, 2024. The Form 4 is a routine insider reporting of a pre-arranged sale and does not include any other transactions or derivative activity.

Michael George Rosenbaum, Guidewire Software, Inc. (GWRE) Chief Executive Officer and director, reported a sale of 1,400 shares of Common Stock on 09/29/2025 at a price of $232.25 per share. After the sale he beneficially owns 262,158 shares. The filing states the sale was an automatic sale pursuant to a 10b5-1 trading plan that Mr. Rosenbaum adopted on October 15, 2024. The Form 4 was executed by Winston King as attorney-in-fact for Mr. Rosenbaum and reflects a routine reported change in beneficial ownership by an insider.

Insider Form 4 filing for Guidewire Software, Inc. (GWRE)

Jeffrey Elliott Cooper, Guidewire's Chief Financial Officer, reported a change in beneficial ownership dated 09/24/2025. The filing shows a disposition of 38 shares of GWRE common stock at $0, recorded under transaction code J(1). Following the reported transaction, Mr. Cooper beneficially owns 77,073 shares, held directly. The form states the 38 shares were transferred as part of a divorce property settlement. The filing was signed by an attorney-in-fact on behalf of Mr. Cooper on 09/25/2025.

Guidewire Software CFO Jeffrey Elliott Cooper reported multiple open-market sales of common stock on 09/18/2025 under a pre-existing 10b5-1 trading plan adopted October 15, 2024. The filings show five separate sales totaling 7,535 shares, executed at average prices reported between approximately $246.05 and $250.75 per share, with the post-transaction beneficial ownership declining to 77,111 shares held directly. The report was signed by an attorney-in-fact on behalf of the reporting person.

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.

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.

John P. Mullen, an officer and President of Guidewire Software, Inc. (GWRE), reported equity award settlement and a sale. On 09/15/2025 Mr. Mullen received 18,543 shares upon settlement of performance-based restricted stock units at no cash price. The next day, 09/16/2025, he sold 15,869 shares to cover taxes at an average sale price of $242.8669 per share. After these transactions he beneficially owned 158,958 shares. The filing explains performance determinations: Part 1 PSUs were adjusted upward based on FY23 ARR results and Part 2 PSUs were awarded after meeting FY25 ARR targets; Part 2 vested on 09/15/2025. The form was signed by an attorney-in-fact on 09/17/2025.

Jeffrey Elliott Cooper, Chief Financial Officer of Guidewire Software, Inc. (GWRE), received 21,194 performance shares on September 15, 2025 as a result of vested performance-based awards and plan mechanics, increasing his beneficial ownership to 98,749 shares. The award description notes earlier adjustments: 249 PSUs were added after FY23 performance and an additional 2,754 PSUs were credited after FY25 performance. On September 16, 2025 Cooper sold 14,103 shares to cover taxes related to RSU settlement at an average sale price of approximately $242.8668 per share, leaving him with 84,646 shares beneficially owned. The performance share award underlying the 21,194 shares is exercisable and converts into common stock and has an indicated expiration/action date of September 15, 2032.

Michael George Rosenbaum, CEO and a director of Guidewire Software, reported changes in his beneficial ownership following performance-share vesting and a sale to cover taxes. On 09/15/2025 the reporting person was issued 45,849 performance shares (PSUs) deemed earned and immediately vested as to Part 2, increasing his direct beneficial ownership to 295,275 shares. On 09/16/2025 he sold 30,317 shares at an average price of approximately $242.8659 per share to cover taxes, leaving 264,958 shares beneficially owned. The filing states the PSUs reflect above-target performance (including a prior 101.8% achievement for FY23 and 120% for FY25) and notes the sale was to satisfy tax withholding on RSU settlement.

Michael George Rosenbaum, CEO and Director of Guidewire Software (GWRE), reported insider transactions. On 09/11/2025 he was credited with 28,958 shares tied to Performance Shares at a reported price of $0, bringing his beneficial ownership to 250,826 shares. The filing notes these Performance Shares are subject to a three-year performance period with continued employment through September 15, 2028.

On 09/15/2025 an automatic sale under a 10b5-1 trading plan executed the disposition of 1,400 shares at $252.83, reducing his beneficial ownership to 249,426. The sale was reported by an attorney-in-fact on behalf of Rosenbaum.

Guidewire Software (GWRE) insider James Winston King received a grant of performance-based equity. On 09/11/2025 Mr. King was awarded 5,687 performance shares that will convert into 5,687 shares of common stock if performance and continued employment conditions are met. The awards cliff vest based on the average results of three one-year performance periods and require continued employment through September 15, 2028. The grant reports $0 as the conversion/exercise price and shows Mr. King beneficially owning 42,329 shares following the transaction. The Form 4 is signed 09/15/2025.

John P. Mullen, President and Director of Guidewire Software, Inc. (GWRE), reported the grant and acquisition of 15,795 performance shares on 09/11/2025 with no cash price. The filing shows 15,795 underlying common shares associated with those performance shares and reports 156,284 shares of common stock beneficially owned following the non-derivative transaction.

The performance shares cliff vest at the end of a three-year performance period based on the average of three one-year performance periods and require continued employment through September 15, 2028. One-year financial targets for each performance period were set at grant. The Form 4 was signed by Winston King as attorney-in-fact on 09/15/2025.

Guidewire Software (GWRE) Chief Accounting Officer David Franklin Peterson reported acquiring 843 shares of the issuer's common stock on 09/11/2025 at a reported price of $0. Following the transaction he beneficially owns 12,796 shares. The Form 4 was filed by one reporting person and signed by an attorney-in-fact on 09/15/2025.

Jeffrey Elliott Cooper, Chief Financial Officer of Guidewire Software, Inc. (GWRE), reported acquisitions on Form 4 dated 09/11/2025. The filing shows an acquisition of 12,636 common shares at a $0 price and the grant of 12,636 performance shares that underlie 12,636 common shares. After the reported transaction, Mr. Cooper beneficially owns 77,555 common shares. The performance shares cliff vest based on the average performance of three one-year periods and require continued employment through September 15, 2028. One-year financial targets for each performance period were set at grant.