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Guidewire Software, Inc. planned insider sales

In the twelve months since 9 October 2025 insiders at Guidewire Software, Inc. filed 87 Form 144 notices of planned sales, 315,079 shares worth $49.3 million at the time of filing, from 14 sellers. The latest, filed 5 October 2026: Mike Rosenbaum (officer, director), 1,200 shares worth $183,024, planned for around 5 October 2026 through Morgan Stanley Smith Barney LLC Executive Financial Services.

FiledSellerRelationshipSharesValuePlanned saleBrokerHow acquiredFiling
5 October 2026Mike RosenbaumOfficer, Director1,200$183,0245 October 2026Morgan Stanley Smith Barney LLC Executive Financial ServicesPerformance SharesForm 144
28 September 2026Mike RosenbaumOfficer, Director1,200$171,18028 September 2026Morgan Stanley Smith Barney LLC Executive Financial ServicesPerformance SharesForm 144
21 September 2026Mike RosenbaumOfficer, Director1,200$175,10421 September 2026Morgan Stanley Smith Barney LLC Executive Financial ServicesPerformance SharesForm 144
18 September 2026James W KingOfficer1,381$200,21718 September 2026Morgan Stanley Smith Barney LLC Executive Financial ServicesRestricted StockForm 144
18 September 2026Jeffrey CooperOfficer9,941$1.4 million18 September 2026Morgan Stanley Smith Barney LLC Executive Financial ServicesPerformance Shares; Restricted StockForm 144
17 September 2026David Franklin PetersonChief Accounting Officer1,905$275,21917 September 2026Morgan Stanley Smith Barney LLC Executive Financial ServicesVesting of PSU (Grant Date: 09/13/2023); Vesting of RSU (Grant Date: 09/11/2024); Vesting of RSU (Grant Date: 09/11/2025); Vesting of RSU (Grant Date: 09/13/2023); Vesting of RSU (Grant Date: 09/15/2022)Form 144
17 September 2026James Winston KingChief Administrative Officer and General Counsel11,814$1.7 million17 September 2026Morgan Stanley Smith Barney LLC Executive Financial ServicesVesting of PSU (Grant Date: 09/13/2023); Vesting of RSU (Grant Date: 09/11/2024); Vesting of RSU (Grant Date: 09/11/2025); Vesting of RSU (Grant Date: 09/13/2023); Vesting of RSU (Grant Date: 09/15/2022)Form 144
17 September 2026Jeffrey Elliott CooperChief Financial Officer23,234$3.4 million17 September 2026Morgan Stanley Smith Barney LLC Executive Financial ServicesVesting of PSU (Grant Date: 09/13/2023); Vesting of RSU (Grant Date: 09/11/2024); Vesting of RSU (Grant Date: 09/11/2025); Vesting of RSU (Grant Date: 09/13/2023); Vesting of RSU (Grant Date: 09/15/2022)Form 144
17 September 2026John P MullenPresident39,683$5.7 million17 September 2026Morgan Stanley Smith Barney LLC Executive Financial ServicesVesting of PSU (Grant Date: 09/13/2023); Vesting of RSU (Grant Date: 09/11/2024); Vesting of RSU (Grant Date: 09/11/2025); Vesting of RSU (Grant Date: 09/13/2023); Vesting of RSU (Grant Date: 09/15/2022)Form 144
17 September 2026Michael George RosenbaumChief Executive Officer72,290$10.4 million17 September 2026Morgan Stanley Smith Barney LLC Executive Financial ServicesVesting of PSU (Grant Date: 09/13/2023); Vesting of RSU (Grant Date: 09/11/2024); Vesting of RSU (Grant Date: 09/11/2025); Vesting of RSU (Grant Date: 09/13/2023); Vesting of RSU (Grant Date: 09/15/2022)Form 144
14 September 2026Mike RosenbaumOfficer, Director1,200$175,04414 September 2026Morgan Stanley Smith Barney LLC Executive Financial ServicesPerformance SharesForm 144
8 September 2026Mike RosenbaumOfficer, Director1,200$192,6248 September 2026Morgan Stanley Smith Barney LLC Executive Financial ServicesPerformance SharesForm 144
31 August 2026Mike RosenbaumOfficer, Director1,200$245,32831 August 2026Morgan Stanley Smith Barney LLC Executive Financial ServicesPerformance SharesForm 144
27 August 2026David F PetersonOfficer2,500$500,00027 August 2026Morgan Stanley Smith Barney LLC Executive Financial ServicesPerformance and Restricted StockForm 144
25 August 2026John MullenOfficer1,800$339,22825 August 2026Morgan Stanley Smith Barney LLC Executive Financial ServicesPerformance SharesForm 144
24 August 2026Mike RosenbaumOfficer, Director1,200$225,38424 August 2026Morgan Stanley Smith Barney LLC Executive Financial ServicesPerformance SharesForm 144
19 August 2026John MullenOfficer16,200$3.0 million19 August 2026Morgan Stanley Smith Barney LLC Executive Financial ServicesRestricted Stock and Performance SharesForm 144
17 August 2026Mike RosenbaumOfficer, Director1,200$207,45617 August 2026Morgan Stanley Smith Barney LLC Executive Financial ServicesPerformance SharesForm 144
10 August 2026Mike RosenbaumOfficer, Director1,200$203,40010 August 2026Morgan Stanley Smith Barney LLC Executive Financial ServicesPerformance SharesForm 144
3 August 2026Mike RosenbaumOfficer, Director1,200$187,1043 August 2026Morgan Stanley Smith Barney LLC Executive Financial ServicesPerformance SharesForm 144
27 July 2026Mike RosenbaumOfficer, Director1,200$170,77227 July 2026Morgan Stanley Smith Barney LLC Executive Financial ServicesPerformance Shares; Restricted StockForm 144
20 July 2026Mike RosenbaumOfficer, Director1,200$176,90420 July 2026Morgan Stanley Smith Barney LLC Executive Financial ServicesRestricted StockForm 144
13 July 2026Mike RosenbaumOfficer, Director1,200$166,16413 July 2026Morgan Stanley Smith Barney LLC Executive Financial ServicesRestricted StockForm 144
9 July 2026James W KingOfficer1,684$219,9989 July 2026Morgan Stanley Smith Barney LLC Executive Financial ServicesRestricted StockForm 144
6 July 2026Mike RosenbaumOfficer, Director1,200$157,9566 July 2026Morgan Stanley Smith Barney LLC Executive Financial ServicesRestricted StockForm 144
29 June 2026Mike RosenbaumOfficer, Director1,200$149,14829 June 2026Morgan Stanley Smith Barney LLC Executive Financial ServicesRestricted StockForm 144
22 June 2026Mike RosenbaumOfficer, Director1,200$126,80422 June 2026Morgan Stanley Smith Barney LLC Executive Financial ServicesPerformance Shares; Restricted StockForm 144
22 June 2026Jeffrey CooperOfficer1,348$142,44322 June 2026Morgan Stanley Smith Barney LLC Executive Financial ServicesRestricted StockForm 144
16 June 2026David F. PetersonChief Accounting Officer246$29,21116 June 2026Morgan Stanley Smith Barney LLC Executive Financial ServicesAcquired as compensation - Restricted Stock UnitsForm 144
16 June 2026James Winston KingChief Administrative Officer and General Counsel999$118,62416 June 2026Morgan Stanley Smith Barney LLC Executive Financial ServicesAcquired as compensation - Restricted Stock UnitsForm 144
16 June 2026Jeffrey Elliott CooperChief Financial Officer2,594$308,01916 June 2026Morgan Stanley Smith Barney LLC Executive Financial ServicesAcquired as compensation - Restricted Stock UnitsForm 144
16 June 2026John P. MullenPresident4,292$509,64516 June 2026Morgan Stanley Smith Barney LLC Executive Financial ServicesAcquired as compensation - Restricted Stock UnitsForm 144
16 June 2026Michael George RosenbaumCEO, Director5,830$692,27216 June 2026Morgan Stanley Smith Barney LLC Executive Financial ServicesAcquired as compensation - Restricted Stock UnitsForm 144
15 June 2026Mike RosenbaumOfficer, Director1,200$148,62015 June 2026Morgan Stanley Smith Barney LLC Executive Financial ServicesPerformance Shares; Restricted StockForm 144
8 June 2026Mike RosenbaumOfficer, Director1,200$162,7448 June 2026Morgan Stanley Smith Barney LLC Executive Financial ServicesRestricted StockForm 144
1 June 2026Mike RosenbaumOfficer, Director1,200$190,7041 June 2026Morgan Stanley Smith Barney LLC Executive Financial ServicesRestricted StockForm 144
26 May 2026Mike RosenbaumOfficer, Director1,200$166,21226 May 2026Morgan Stanley Smith Barney LLC Executive Financial ServicesRestricted StockForm 144
18 May 2026Mike RosenbaumOfficer, Director1,200$153,82818 May 2026Morgan Stanley Smith Barney LLC Executive Financial ServicesRestricted StockForm 144
11 May 2026Mike RosenbaumOfficer, Director1,200$163,65611 May 2026Morgan Stanley Smith Barney LLC Executive Financial ServicesRestricted StockForm 144
4 May 2026Mike RosenbaumOfficer, Director1,200$170,2924 May 2026Morgan Stanley Smith Barney LLC Executive Financial ServicesRestricted StockForm 144
27 April 2026Mike RosenbaumOfficer, Director1,200$165,70827 April 2026Morgan Stanley Smith Barney LLC Executive Financial ServicesPerformance Shares; Restricted StockForm 144
20 April 2026Mike RosenbaumOfficer, Director1,200$167,70020 April 2026Morgan Stanley Smith Barney LLC Executive Financial ServicesPerformance Shares; Restricted StockForm 144
13 April 2026Mike RosenbaumOfficer, Director1,200$142,52413 April 2026Morgan Stanley Smith Barney LLC Executive Financial ServicesRestricted StockForm 144
6 April 2026Mike RosenbaumOfficer, Director1,200$181,3686 April 2026Morgan Stanley Smith Barney LLC Executive Financial ServicesRestricted StockForm 144
30 March 2026Mike RosenbaumOfficer, Director1,200$174,88830 March 2026Morgan Stanley Smith Barney LLC Executive Financial ServicesRestricted StockForm 144
23 March 2026Mike RosenbaumOfficer, Director1,200$186,67223 March 2026Morgan Stanley Smith Barney LLC Executive Financial ServicesRestricted StockForm 144
17 March 2026David F. PetersonChief Accounting Officer273$44,73317 March 2026Morgan Stanley Smith Barney LLC Executive Financial ServicesAcquired as compensation - Restricted Stock UnitsForm 144
17 March 2026James Winston KingChief Administrative Officer and General Counsel1,001$164,02217 March 2026Morgan Stanley Smith Barney LLC Executive Financial ServicesAcquired as compensation - Restricted Stock UnitsForm 144
17 March 2026Jeffrey Elliott CooperChief Financial Officer1,935$317,06517 March 2026Morgan Stanley Smith Barney LLC Executive Financial ServicesAcquired as compensation - Restricted Stock UnitsForm 144
17 March 2026Michael G. RosenbaumChief Executive Officer4,737$776,19517 March 2026Morgan Stanley Smith Barney LLC Executive Financial ServicesAcquired as compensation - Restricted Stock UnitsForm 144
17 March 2026John P. MullenPresident6,576$1.1 million17 March 2026Morgan Stanley Smith Barney LLC Executive Financial ServicesAcquired as compensation - Restricted Stock UnitsForm 144
16 March 2026Mike RosenbaumOfficer, Director1,200$192,00016 March 2026Morgan Stanley Smith Barney LLC Executive Financial ServicesPerformance Shares; Restricted StockForm 144
13 March 2026Jeffrey CooperOfficer4,757$755,03113 March 2026Morgan Stanley Smith Barney LLC Executive Financial ServicesPerformance Shares; Restricted StockForm 144
9 March 2026Mike RosenbaumOfficer, Director1,200$199,6089 March 2026Morgan Stanley Smith Barney LLC Executive Financial ServicesPerformance Shares; Restricted StockForm 144
2 March 2026Mike RosenbaumOfficer, Director1,200$172,6442 March 2026Morgan Stanley Smith Barney LLC Executive Financial ServicesRestricted StockForm 144
23 February 2026Mike RosenbaumOfficer, Director1,200$150,60023 February 2026Morgan Stanley Smith Barney LLC Executive Financial ServicesRestricted StockForm 144
17 February 2026Mike RosenbaumOfficer, Director1,200$152,40017 February 2026Morgan Stanley Smith Barney LLC Executive Financial ServicesPerformance Shares; Restricted StockForm 144
9 February 2026Mike RosenbaumOfficer, Director1,200$153,3249 February 2026Morgan Stanley Smith Barney LLC Executive Financial ServicesPerformance SharesForm 144
4 February 2026Lavin PaulFormer Director4,878$612,8724 February 2026Fidelity Brokerage Services LLCStock AwardForm 144
2 February 2026Mike RosenbaumOfficer, Director1,200$168,0122 February 2026Morgan Stanley Smith Barney LLC Executive Financial ServicesPerformance SharesForm 144
26 January 2026Mike RosenbaumOfficer, Director1,200$192,38426 January 2026Morgan Stanley Smith Barney LLC Executive Financial ServicesPerformance SharesForm 144
20 January 2026Mike RosenbaumOfficer, Director1,200$187,51220 January 2026Morgan Stanley Smith Barney LLC Executive Financial ServicesPerformance SharesForm 144
13 January 2026Jeffrey CooperOfficer216$39,06813 January 2026Morgan Stanley Smith Barney LLC Executive Financial ServicesRestricted StockForm 144
13 January 2026Mike RosenbaumOfficer, Director1,200$217,04413 January 2026Morgan Stanley Smith Barney LLC Executive Financial ServicesPerformance SharesForm 144
29 December 2025Mike RosenbaumOfficer, Director1,400$286,93029 December 2025Morgan Stanley Smith Barney LLC Executive Financial ServicesPerformance SharesForm 144
22 December 2025Mike RosenbaumOfficer, Director1,400$281,00822 December 2025Morgan Stanley Smith Barney LLC Executive Financial ServicesPerformance SharesForm 144
18 December 2025Jeffrey CooperOfficer1,232$240,24018 December 2025Morgan Stanley Smith Barney LLC Executive Financial ServicesRestricted StockForm 144
18 December 2025James W KingOfficer1,860$362,70018 December 2025Morgan Stanley Smith Barney LLC Executive Financial ServicesPerformance Shares; Restricted StockForm 144
16 December 2025David Franklin PetersonChief Accounting Officer358$68,76316 December 2025Morgan Stanley Smith Barney LLC Executive Financial ServicesAcquired as compensation - Restricted Stock UnitsForm 144
16 December 2025James Winston KingChief Admin Officer and General Counsel1,457$279,85516 December 2025Morgan Stanley Smith Barney LLC Executive Financial ServicesAcquired as compensation - Restricted Stock UnitsForm 144
16 December 2025Jeffrey Elliott CooperChief Financial Officer2,872$551,64316 December 2025Morgan Stanley Smith Barney LLC Executive Financial ServicesAcquired as compensation - Restricted Stock UnitsForm 144
16 December 2025Michael George RosenbaumChief Executive Officer6,015$1.2 million16 December 2025Morgan Stanley Smith Barney LLC Executive Financial ServicesAcquired as compensation - Restricted Stock UnitsForm 144
16 December 2025John P MullenPresident7,975$1.5 million16 December 2025Morgan Stanley Smith Barney LLC Executive Financial ServicesAcquired as compensation - Restricted Stock UnitsForm 144
15 December 2025Mike RosenbaumOfficer, Director1,400$286,07615 December 2025Morgan Stanley Smith Barney LLC Executive Financial ServicesPerformance SharesForm 144
8 December 2025Mike RosenbaumOfficer, Director1,400$295,2188 December 2025Morgan Stanley Smith Barney LLC Executive Financial ServicesPerformance SharesForm 144
1 December 2025Mike RosenbaumOfficer, Director1,400$298,8161 December 2025Morgan Stanley Smith Barney LLC Executive Financial ServicesPerformance SharesForm 144
1 December 2025John MullenOfficer3,000$640,3201 December 2025Morgan Stanley Smith Barney LLC Executive Financial ServicesPerformance Shares; Restricted StockForm 144
24 November 2025Mike RosenbaumOfficer, Director1,400$298,52224 November 2025Morgan Stanley Smith Barney LLC Executive Financial ServicesPerformance SharesForm 144
17 November 2025James W KingOfficer798$177,58717 November 2025Morgan Stanley Smith Barney LLC Executive Financial ServicesPerformance Shares; Restricted StockForm 144
17 November 2025Mike RosenbaumOfficer, Director1,400$311,55617 November 2025Morgan Stanley Smith Barney LLC Executive Financial ServicesPerformance SharesForm 144
10 November 2025Mike RosenbaumOfficer, Director1,400$305,94210 November 2025Morgan Stanley Smith Barney LLC Executive Financial ServicesPerformance SharesForm 144
3 November 2025Mike RosenbaumOfficer, Director1,400$324,5903 November 2025Morgan Stanley Smith Barney LLC Executive Financial ServicesPerformance SharesForm 144
3 November 2025John MullenOfficer3,000$695,5503 November 2025Morgan Stanley Smith Barney LLC Executive Financial ServicesRestricted StockForm 144
27 October 2025Mike RosenbaumOfficer, Director1,400$357,56027 October 2025Morgan Stanley Smith Barney LLC Executive Financial ServicesPerformance SharesForm 144
20 October 2025James W KingOfficer798$196,06920 October 2025Morgan Stanley Smith Barney LLC Executive Financial ServicesPerformance Shares; Restricted StockForm 144
20 October 2025Mike RosenbaumOfficer, Director1,400$343,98020 October 2025Morgan Stanley Smith Barney LLC Executive Financial ServicesPerformance Shares; Restricted StockForm 144
14 October 2025Mike RosenbaumOfficer, Director1,400$335,59413 October 2025Morgan Stanley Smith Barney LLC Executive Financial ServicesRestricted StockForm 144
A Form 144 is the notice an insider files with the SEC before selling restricted or control shares over the Rule 144 thresholds; it says what may be sold, not what was.
Read moreValue is the filer's own aggregate market value. Whether the sale happened shows up later on Form 4, on the insiders page.

Source

Form 144 filings on EDGAR for Guidewire Software, Inc.: the company's filing index, each notice read from its own XML.

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