X0306 4 2020-09-15 0 0001528396 Guidewire Software, Inc. GWRE 0001586253 King James Winston 2850 SOUTH DELAWARE ST., SUITE 400 SAN MATEO CA 94403 0 1 0 0 Chief Admin Officer, Gen Couns Common Stock 2020-09-15 4 M 0 5681 0.0 A 9891 D Common Stock 2020-09-17 4 S 0 2176 105.2922 D 7715 D Performance Shares 0.0 2020-09-15 4 M 0 269 0.0 D 2026-09-13 Common Stock 269 44 D Performance Shares 0.0 2020-09-15 4 M 0 291 0.0 D 2027-09-12 Common Stock 291 3615 D Performance Shares 0.0 2020-09-15 4 M 0 2027 0.0 D 2027-09-12 Common Stock 2027 1588 D Performance Shares 0.0 2020-09-15 4 M 0 275 0.0 D 2028-09-12 Common Stock 275 4305 D Performance Shares 0.0 2020-09-15 4 M 0 767 0.0 D 2029-09-06 Common Stock 767 6233 D Restricted Stock Unit 0.0 2020-09-15 4 M 0 438 0.0 D 2026-09-13 Common Stock 438 0 D Restricted Stock Unit 0.0 2020-09-15 4 M 0 444 0.0 D 2027-09-12 Common Stock 444 1775 D Restricted Stock Unit 0.0 2020-09-15 4 M 0 407 0.0 D 2028-09-12 Common Stock 407 3250 D Restricted Stock Unit 0.0 2020-09-15 4 M 0 325 0.0 D 2029-06-12 Common Stock 325 3581 D Restricted Stock Unit 0.0 2020-09-15 4 M 0 438 0.0 D 2029-09-06 Common Stock 438 5250 D Shares sold by Issuer to cover taxes associated with settlement of Restricted Stock Units. The sale price reported in column 4 of Table 1 represents the average sale price of the shares sold ranging from $105.2906 to $105.2942 per share. The reporting person will provide, upon request by the Commission staff, the issuer, or a security holder of the issuer, full information regarding the number of shares sold at each separate price. The grant consists of three separate issuances of Restricted Stock Units, each with vesting subject to the Reporting Person's continued service to the Issuer. The first is 7,000 units vesting as follows: 1/16th of the units vest quarterly commencing December 15, 2016. The second is 4,301 units, for which vesting was subject to the satisfaction of both performance-based conditions and time-based criteria. The performance-based conditions were deemed met and exceeded by the Issuer's Board of Directors, and the time-based vesting criteria are as follows: 1/4th of the units vested on September 15, 2017 and an additional 1/16th of the units will vest quarterly thereafter. The third previously described TSR grant has vested according to its terms and conditions. Shares are adjusted based on the attainment of the performance-based conditions as determined by the Issuer's Board of Directors based on the Company's results FYE July 31, 2016, and July 31, 2019. The grant consists of three separate issuances of Restricted Stock Units, each with vesting subject to the Reporting Person's continued service to the Issuer. The first is 7,100 units vesting as follows: 1/16th of the units vest quarterly commencing December 15, 2017. The second is 4,647 units, for which vesting was subject to the satisfaction of both performance-based conditions and time-based criteria. The performance-based conditions were deemed met and exceeded by the Issuer's Board of Directors, and the time-based vesting criteria are as follows: 1/4th of the units vested on September 15, 2018 and an additional 1/16th of the units will vest quarterly thereafter. The third consists of units for which vesting will be determined based on the Issuer's total shareholder return percentile ranking relative to a set peer group, over a three year period ending on July 31, 2020. The number of shares reported in Column 9 of Table II represents the 2017 Performance Stock Unit ("PSU") and the Total Shareholder Return ("TSR") grants less the number of PSU and TSR shares vested as of this Transaction Date. The actual number of Performance Restricted Stock Units ("TSRs") earned based on the Issuer's total shareholder return percentile ranking relative to the companies in the S&P Software and Services Select Industry Index for a three-year cumulative performance period commencing August 1, 2017 and ending July 31, 2020, as affirmed by the Issuer's board of directors. All earned TSRs vested on September 15, 2020, subject to the Reporting Person's continued service to the Issuer. The grant consists of three separate issuances of Restricted Stock Units, each with vesting subject to the Reporting Person's continued service to the Issuer. The first is 6,500 units vesting as follows: 1/16th of the units vest quarterly commencing December 15, 2018. The second is 4,391 units, for which vesting was subject to the satisfaction of both performance-based conditions and time-based criteria. The performance-based conditions were deemed met and exceeded by the Issuer's Board of Directors, and the time-based vesting criteria are as follows: 1/4th of the units vested on September 15, 2019 and an additional 1/16th of the units will vest quarterly thereafter. The third consists of units for which vesting will be determined based on the Issuer's total shareholder return percentile ranking relative to a set peer group, over a three year period ending on July 31, 2021. The number of shares reported in Column 9 of Table II represents the 2018 Performance Stock Unit ("PSU") and the Total Shareholder Return ("TSR") grants less the number of PSU shares vested as of this Transaction Date. The grant consists of three separate issuances of Restricted Stock Units, each with vesting subject to the Reporting Person's continued service to the Issuer. The first is 7,000 units vesting as follows: 1/16th of the units vest quarterly commencing December 15, 2019. The second is 3,066 units, for which vesting was subject to the satisfaction of both performance-based conditions and time-based criteria. Attainment regarding the performance-based conditions was determined by the Issuer's Board of Directors based on the Issuer's results for FYE July 31, 2020, and the time-based vesting criteria are as follows: 1/4th of the units vested on September 15, 2020 and an additional 1/16th of the units will vest quarterly thereafter. The third consists of units for which vesting will be determined based on the Issuer's total shareholder return percentile ranking relative to a set peer group, over a three year period ending on July 31, 2022. The number of shares reported in Column 9 of Table II represents the 2019 Performance Stock Unit ("PSU") and the Total Shareholder Return ("TSR") grants less the number of PSU shares vested as of this Transaction Date. The Restricted Stock Units vest as follows: 1/16th of the units vest quarterly commencing September 15, 2019, subject to the Reporting Person's continued service to the Issuer. James Winston King 2020-09-17