King James Winston, Chief Administrative Officer and General Counsel at Guidewire Software ($GWRE), sold about $6.4 million worth of company shares across 16 open market transactions over the past year. His most recent sale occurred on December 18, 2025. These sales rank him 1,606th among over 11,600 insiders by total value sold, below the average of $8.6 million per seller and 6.4 transactions. Winston made no open market purchases in this period.
| Transaction Date | Company | Ticker | Insider Name | Title | Transaction Type | Security | Shares | Price | Shares Owned Following | Total Shares Outstanding | % of Owned | % of Outstanding |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| March 17, 2026 | Guidewire Software, Inc. | $GWRE | King James Winston | Chief Admin Officer, Gen Couns | S | Common Stock | 1001 | $163.86 | 32,701.0000 | 86,451,737 | 2.97% | 0.00% |
| Dec. 16, 2025 | Guidewire Software, Inc. | $GWRE | King James Winston | Chief Admin Officer, Gen Couns | S | Common Stock | 1457 | $192.08 | 35,562.0000 | 86,451,737 | 3.94% | 0.00% |
| Dec. 18, 2025 | Guidewire Software, Inc. | $GWRE | King James Winston | Chief Admin Officer, Gen Couns | S | Common Stock | 1860 | $195.00 | 33,702.0000 | 86,451,737 | 5.23% | 0.00% |
| Nov. 17, 2025 | Guidewire Software, Inc. | $GWRE | King James Winston | Chief Admin Officer, Gen Couns | S | Common Stock | 798 | $222.54 | 37,019.0000 | 86,451,737 | 2.11% | 0.00% |
| Oct. 20, 2025 | Guidewire Software, Inc. | $GWRE | King James Winston | Chief Admin Officer, Gen Couns | S | Common Stock | 798 | $245.70 | 37,817.0000 | 85,911,653 | 2.07% | 0.00% |
| Sept. 18, 2025 | Guidewire Software, Inc. | $GWRE | King James Winston | Chief Admin Officer, Gen Couns | S | Common Stock | 2147 | $250.12 | 38,615.0000 | 85,911,653 | 5.27% | 0.00% |
| Sept. 18, 2025 | Guidewire Software, Inc. | $GWRE | King James Winston | Chief Admin Officer, Gen Couns | S | Common Stock | 1197 | $248.16 | 42,702.0000 | 85,911,653 | 2.73% | 0.00% |
| Sept. 18, 2025 | Guidewire Software, Inc. | $GWRE | King James Winston | Chief Admin Officer, Gen Couns | S | Common Stock | 1878 | $247.21 | 43,899.0000 | 85,911,653 | 4.10% | 0.00% |
| Sept. 18, 2025 | Guidewire Software, Inc. | $GWRE | King James Winston | Chief Admin Officer, Gen Couns | S | Common Stock | 1940 | $249.35 | 40,762.0000 | 85,911,653 | 4.54% | 0.00% |
| Sept. 16, 2025 | Guidewire Software, Inc. | $GWRE | King James Winston | Chief Admin Officer, Gen Couns | S | Common Stock | 7149 | $242.87 | 45,777.0000 | 85,911,653 | 13.51% | 0.01% |
| Sept. 15, 2025 | Guidewire Software, Inc. | $GWRE | King James Winston | Chief Admin Officer, Gen Couns | M | Common Stock | 10597 | $0.00 | 52,926.0000 | 85,911,653 | 25.03% | 0.01% |
| Sept. 15, 2025 | Guidewire Software, Inc. | $GWRE | King James Winston | Chief Admin Officer, Gen Couns | M | Performance Shares | 10597 | $0.00 | 0.0000 | 85,911,653 | 100.00% | 0.01% |
| Sept. 11, 2025 | Guidewire Software, Inc. | $GWRE | King James Winston | Chief Admin Officer, Gen Couns | A | Performance Shares | 5687 | $0.00 | 5,687.0000 | 85,911,653 | 9999.99% | 0.01% |
| Sept. 11, 2025 | Guidewire Software, Inc. | $GWRE | King James Winston | Chief Admin Officer, Gen Couns | A | Common Stock | 5687 | $0.00 | 42,329.0000 | 85,911,653 | 15.52% | 0.01% |
| Aug. 18, 2025 | Guidewire Software, Inc. | $GWRE | King James Winston | Chief Admin Officer, Gen Couns | S | Common Stock | 799 | $211.61 | 36,642.0000 | 85,911,653 | 2.13% | 0.00% |
| July 14, 2025 | Guidewire Software, Inc. | $GWRE | King James Winston | Chief Admin Officer, Gen Couns | S | Common Stock | 2482 | $220.65 | 37,441.0000 | 85,960,868 | 6.22% | 0.00% |
| June 17, 2025 | Guidewire Software, Inc. | $GWRE | King James Winston | Chief Admin Officer, Gen Couns | S | Common Stock | 1230 | $248.94 | 39,923.0000 | 85,960,868 | 2.99% | 0.00% |
| March 19, 2025 | Guidewire Software, Inc. | $GWRE | King James Winston | Chief Admin Officer, Gen Couns | S | Common Stock | 1827 | $193.51 | 41,945.0000 | 85,960,868 | 4.17% | 0.00% |
| March 18, 2025 | Guidewire Software, Inc. | $GWRE | King James Winston | Chief Admin Officer, Gen Couns | S | Common Stock | 1051 | $189.41 | 44,613.0000 | 85,960,868 | 2.30% | 0.00% |
| March 19, 2025 | Guidewire Software, Inc. | $GWRE | King James Winston | Chief Admin Officer, Gen Couns | S | Common Stock | 841 | $191.30 | 43,772.0000 | 85,960,868 | 1.89% | 0.00% |
| March 19, 2025 | Guidewire Software, Inc. | $GWRE | King James Winston | Chief Admin Officer, Gen Couns | S | Common Stock | 792 | $194.61 | 41,153.0000 | 85,960,868 | 1.89% | 0.00% |
| Jan. 15, 2025 | Guidewire Software, Inc. | $GWRE | King James Winston | Chief Admin Officer, Gen Couns | S | Common Stock | 270 | $174.78 | 45,664.0000 | 85,960,868 | 0.59% | 0.00% |
| Dec. 17, 2024 | Guidewire Software, Inc. | $GWRE | King James Winston | Chief Admin Officer, Gen Couns | S | Common Stock | 1509 | $171.06 | 46,728.0000 | 85,960,868 | 3.13% | 0.00% |
| Dec. 19, 2024 | Guidewire Software, Inc. | $GWRE | King James Winston | Chief Admin Officer, Gen Couns | S | Common Stock | 794 | $174.43 | 45,934.0000 | 85,960,868 | 1.70% | 0.00% |
| Sept. 19, 2024 | Guidewire Software, Inc. | $GWRE | King James Winston | Chief Admin Officer, Gen Couns | S | Common Stock | 138 | $173.88 | 48,237.0000 | 82,291,483 | 0.29% | 0.00% |
| Sept. 17, 2024 | Guidewire Software, Inc. | $GWRE | King James Winston | Chief Admin Officer, Gen Couns | S | Common Stock | 5798 | $172.16 | 52,751.0000 | 82,291,483 | 9.90% | 0.01% |
| Sept. 19, 2024 | Guidewire Software, Inc. | $GWRE | King James Winston | Chief Admin Officer, Gen Couns | S | Common Stock | 1309 | $171.94 | 51,442.0000 | 82,291,483 | 2.48% | 0.00% |
| Sept. 19, 2024 | Guidewire Software, Inc. | $GWRE | King James Winston | Chief Admin Officer, Gen Couns | S | Common Stock | 3067 | $172.91 | 48,375.0000 | 82,291,483 | 5.96% | 0.00% |
| Sept. 15, 2024 | Guidewire Software, Inc. | $GWRE | King James Winston | Chief Admin Officer, Gen Couns | M | Performance Shares | 6563 | $0.00 | 0.0000 | 82,291,483 | 100.00% | 0.01% |
| Sept. 15, 2024 | Guidewire Software, Inc. | $GWRE | King James Winston | Chief Admin Officer, Gen Couns | M | Performance Shares | 2335 | $0.00 | 9,220.0000 | 82,291,483 | 20.21% | 0.00% |
| Sept. 15, 2024 | Guidewire Software, Inc. | $GWRE | King James Winston | Chief Admin Officer, Gen Couns | M | Common Stock | 6563 | $0.00 | 58,549.0000 | 82,291,483 | 12.62% | 0.01% |
| Sept. 15, 2024 | Guidewire Software, Inc. | $GWRE | King James Winston | Chief Admin Officer, Gen Couns | M | Common Stock | 2335 | $0.00 | 51,986.0000 | 82,291,483 | 4.70% | 0.00% |
| Sept. 11, 2024 | Guidewire Software, Inc. | $GWRE | King James Winston | Chief Admin Officer, Gen Couns | A | Common Stock | 8967 | $0.00 | 49,651.0000 | 82,291,483 | 22.04% | 0.01% |
| Sept. 11, 2024 | Guidewire Software, Inc. | $GWRE | King James Winston | Chief Admin Officer, Gen Couns | A | Performance Shares | 8967 | $0.00 | 8,967.0000 | 82,291,483 | 9999.99% | 0.01% |
| Aug. 21, 2024 | Guidewire Software, Inc. | $GWRE | King James Winston | Chief Admin Officer, Gen Couns | M | Non-Qualified Stock Option (right to buy) | 105 | $0.00 | 0.0000 | 82,291,483 | 100.00% | 0.00% |
| Aug. 21, 2024 | Guidewire Software, Inc. | $GWRE | King James Winston | Chief Admin Officer, Gen Couns | M | Common Stock | 105 | $45.27 | 40,789.0000 | 82,291,483 | 0.26% | 0.00% |
| Aug. 21, 2024 | Guidewire Software, Inc. | $GWRE | King James Winston | Chief Admin Officer, Gen Couns | S | Common Stock | 105 | $146.97 | 40,684.0000 | 82,291,483 | 0.26% | 0.00% |
| June 20, 2024 | Guidewire Software, Inc. | $GWRE | King James Winston | Chief Admin Officer, Gen Couns | S | Common Stock | 1316 | $134.20 | 40,684.0000 | 82,176,629 | 3.13% | 0.00% |
| June 18, 2024 | Guidewire Software, Inc. | $GWRE | King James Winston | Chief Admin Officer, Gen Couns | S | Common Stock | 1036 | $134.54 | 42,000.0000 | 82,176,629 | 2.41% | 0.00% |
| March 19, 2024 | Guidewire Software, Inc. | $GWRE | King James Winston | Chief Admin Officer, Gen Couns | S | Common Stock | 1106 | $111.74 | 44,304.0000 | 82,176,629 | 2.44% | 0.00% |
| March 20, 2024 | Guidewire Software, Inc. | $GWRE | King James Winston | Chief Admin Officer, Gen Couns | S | Common Stock | 1268 | $112.51 | 43,036.0000 | 82,176,629 | 2.86% | 0.00% |
| Jan. 11, 2024 | Guidewire Software, Inc. | $GWRE | King James Winston | Chief Admin Officer, Gen Couns | S | Common Stock | 1075 | $110.77 | 45,410.0000 | 82,176,629 | 2.31% | 0.00% |