Michael George Rosenbaum, CEO of Guidewire Software ($GWRE), sold shares on the open market 55 times over the last year, totaling $25.4 million. His most recent sale occurred on March 9, 2026. These sales rank 555th among nearly 12,000 insiders in our database, outpacing the average of $8.6 million per seller and 6.4 transactions. Rosenbaum 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 30, 2026 | Guidewire Software, Inc. | $GWRE | Rosenbaum Michael George | Chief Executive Officer | S | Common Stock | 1200 | $145.74 | 218,806.0000 | 86,451,737 | 0.55% | 0.00% |
| March 23, 2026 | Guidewire Software, Inc. | $GWRE | Rosenbaum Michael George | Chief Executive Officer | S | Common Stock | 1200 | $155.56 | 220,006.0000 | 86,451,737 | 0.54% | 0.00% |
| March 17, 2026 | Guidewire Software, Inc. | $GWRE | Rosenbaum Michael George | Chief Executive Officer | S | Common Stock | 4737 | $163.86 | 221,206.0000 | 86,451,737 | 2.10% | 0.01% |
| March 16, 2026 | Guidewire Software, Inc. | $GWRE | Rosenbaum Michael George | Chief Executive Officer | S | Common Stock | 1200 | $160.00 | 225,943.0000 | 86,451,737 | 0.53% | 0.00% |
| March 9, 2026 | Guidewire Software, Inc. | $GWRE | Rosenbaum Michael George | Chief Executive Officer | S | Common Stock | 1200 | $166.34 | 227,143.0000 | 86,451,737 | 0.53% | 0.00% |
| March 2, 2026 | Guidewire Software, Inc. | $GWRE | Rosenbaum Michael George | Chief Executive Officer | S | Common Stock | 1200 | $143.87 | 228,343.0000 | 86,451,737 | 0.52% | 0.00% |
| March 3, 2026 | DOCUSIGN, INC. | $DOCU | Rosenbaum Michael George | Director | M | Common Stock | 522 | $0.00 | 1,044.0000 | 210,605,000 | 100.00% | 0.00% |
| March 3, 2026 | DOCUSIGN, INC. | $DOCU | Rosenbaum Michael George | Director | M | Restricted Stock Units | 522 | $0.00 | 5,221.0000 | 210,605,000 | 9.09% | 0.00% |
| Feb. 23, 2026 | Guidewire Software, Inc. | $GWRE | Rosenbaum Michael George | Chief Executive Officer | S | Common Stock | 1200 | $125.50 | 229,543.0000 | 86,451,737 | 0.52% | 0.00% |
| Feb. 17, 2026 | Guidewire Software, Inc. | $GWRE | Rosenbaum Michael George | Chief Executive Officer | S | Common Stock | 1200 | $127.00 | 230,743.0000 | 86,451,737 | 0.52% | 0.00% |
| Feb. 9, 2026 | Guidewire Software, Inc. | $GWRE | Rosenbaum Michael George | Chief Executive Officer | S | Common Stock | 1200 | $127.77 | 231,943.0000 | 86,451,737 | 0.51% | 0.00% |
| Feb. 2, 2026 | Guidewire Software, Inc. | $GWRE | Rosenbaum Michael George | Chief Executive Officer | S | Common Stock | 1200 | $140.01 | 233,143.0000 | 86,451,737 | 0.51% | 0.00% |
| Jan. 26, 2026 | Guidewire Software, Inc. | $GWRE | Rosenbaum Michael George | Chief Executive Officer | S | Common Stock | 1200 | $160.32 | 234,343.0000 | 86,451,737 | 0.51% | 0.00% |
| Jan. 20, 2026 | Guidewire Software, Inc. | $GWRE | Rosenbaum Michael George | Chief Executive Officer | S | Common Stock | 1200 | $156.26 | 235,543.0000 | 86,451,737 | 0.51% | 0.00% |
| Jan. 13, 2026 | Guidewire Software, Inc. | $GWRE | Rosenbaum Michael George | Chief Executive Officer | S | Common Stock | 1200 | $180.87 | 236,743.0000 | 86,451,737 | 0.50% | 0.00% |
| Dec. 29, 2025 | Guidewire Software, Inc. | $GWRE | Rosenbaum Michael George | Chief Executive Officer | S | Common Stock | 1400 | $204.95 | 237,943.0000 | 86,451,737 | 0.58% | 0.00% |
| Dec. 22, 2025 | Guidewire Software, Inc. | $GWRE | Rosenbaum Michael George | Chief Executive Officer | S | Common Stock | 1400 | $200.72 | 239,343.0000 | 86,451,737 | 0.58% | 0.00% |
| Dec. 16, 2025 | Guidewire Software, Inc. | $GWRE | Rosenbaum Michael George | Chief Executive Officer | S | Common Stock | 6015 | $192.08 | 240,743.0000 | 86,451,737 | 2.44% | 0.01% |
| Dec. 15, 2025 | Guidewire Software, Inc. | $GWRE | Rosenbaum Michael George | Chief Executive Officer | S | Common Stock | 1400 | $204.34 | 246,758.0000 | 86,451,737 | 0.56% | 0.00% |
| Dec. 8, 2025 | Guidewire Software, Inc. | $GWRE | Rosenbaum Michael George | Chief Executive Officer | S | Common Stock | 1400 | $210.87 | 248,158.0000 | 86,451,737 | 0.56% | 0.00% |
| Dec. 3, 2025 | DOCUSIGN, INC. | $DOCU | Rosenbaum Michael George | Director | M | Common Stock | 522 | $0.00 | 522.0000 | 210,605,000 | 9999.99% | 0.00% |
| Dec. 3, 2025 | DOCUSIGN, INC. | $DOCU | Rosenbaum Michael George | Director | M | Restricted Stock Units | 522 | $0.00 | 5,743.0000 | 210,605,000 | 8.33% | 0.00% |
| Dec. 1, 2025 | Guidewire Software, Inc. | $GWRE | Rosenbaum Michael George | Chief Executive Officer | S | Common Stock | 1400 | $213.44 | 249,558.0000 | 86,451,737 | 0.56% | 0.00% |
| Nov. 24, 2025 | Guidewire Software, Inc. | $GWRE | Rosenbaum Michael George | Chief Executive Officer | S | Common Stock | 1400 | $213.23 | 250,958.0000 | 86,451,737 | 0.55% | 0.00% |
| Nov. 17, 2025 | Guidewire Software, Inc. | $GWRE | Rosenbaum Michael George | Chief Executive Officer | S | Common Stock | 1400 | $222.54 | 252,358.0000 | 86,451,737 | 0.55% | 0.00% |
| Nov. 10, 2025 | Guidewire Software, Inc. | $GWRE | Rosenbaum Michael George | Chief Executive Officer | S | Common Stock | 1400 | $218.53 | 253,758.0000 | 86,451,737 | 0.55% | 0.00% |
| Nov. 3, 2025 | Guidewire Software, Inc. | $GWRE | Rosenbaum Michael George | Chief Executive Officer | S | Common Stock | 1400 | $231.85 | 255,158.0000 | 86,451,737 | 0.55% | 0.00% |
| Oct. 27, 2025 | Guidewire Software, Inc. | $GWRE | Rosenbaum Michael George | Chief Executive Officer | S | Common Stock | 1400 | $255.40 | 256,558.0000 | 85,911,653 | 0.54% | 0.00% |
| Oct. 20, 2025 | Guidewire Software, Inc. | $GWRE | Rosenbaum Michael George | Chief Executive Officer | S | Common Stock | 1400 | $245.70 | 257,958.0000 | 85,911,653 | 0.54% | 0.00% |
| Oct. 13, 2025 | Guidewire Software, Inc. | $GWRE | Rosenbaum Michael George | Chief Executive Officer | S | Common Stock | 1400 | $239.71 | 259,358.0000 | 85,911,653 | 0.54% | 0.00% |
| Oct. 6, 2025 | Guidewire Software, Inc. | $GWRE | Rosenbaum Michael George | Chief Executive Officer | S | Common Stock | 1400 | $230.08 | 260,758.0000 | 85,911,653 | 0.53% | 0.00% |
| Sept. 29, 2025 | Guidewire Software, Inc. | $GWRE | Rosenbaum Michael George | Chief Executive Officer | S | Common Stock | 1400 | $232.25 | 262,158.0000 | 85,911,653 | 0.53% | 0.00% |
| Sept. 22, 2025 | Guidewire Software, Inc. | $GWRE | Rosenbaum Michael George | Chief Executive Officer | S | Common Stock | 1400 | $244.55 | 263,558.0000 | 85,911,653 | 0.53% | 0.00% |
| Sept. 15, 2025 | Guidewire Software, Inc. | $GWRE | Rosenbaum Michael George | Chief Executive Officer | M | Common Stock | 45849 | $0.00 | 295,275.0000 | 85,911,653 | 18.38% | 0.05% |
| Sept. 16, 2025 | Guidewire Software, Inc. | $GWRE | Rosenbaum Michael George | Chief Executive Officer | S | Common Stock | 30317 | $242.87 | 264,958.0000 | 85,911,653 | 10.27% | 0.04% |
| Sept. 15, 2025 | Guidewire Software, Inc. | $GWRE | Rosenbaum Michael George | Chief Executive Officer | M | Performance Shares | 45849 | $0.00 | 0.0000 | 85,911,653 | 100.00% | 0.05% |
| Sept. 11, 2025 | Guidewire Software, Inc. | $GWRE | Rosenbaum Michael George | Chief Executive Officer | A | Performance Shares | 28958 | $0.00 | 28,958.0000 | 85,911,653 | 9999.99% | 0.03% |
| Sept. 15, 2025 | Guidewire Software, Inc. | $GWRE | Rosenbaum Michael George | Chief Executive Officer | S | Common Stock | 1400 | $252.83 | 249,426.0000 | 85,911,653 | 0.56% | 0.00% |
| Sept. 11, 2025 | Guidewire Software, Inc. | $GWRE | Rosenbaum Michael George | Chief Executive Officer | A | Common Stock | 28958 | $0.00 | 250,826.0000 | 85,911,653 | 13.05% | 0.03% |
| Sept. 9, 2025 | DOCUSIGN, INC. | $DOCU | Rosenbaum Michael George | Director | A | Restricted Stock Units | 6265 | $0.00 | 6,265.0000 | 210,339,000 | 9999.99% | 0.00% |
| Sept. 8, 2025 | Guidewire Software, Inc. | $GWRE | Rosenbaum Michael George | Chief Executive Officer | S | Common Stock | 1400 | $261.28 | 221,868.0000 | 85,911,653 | 0.63% | 0.00% |
| Sept. 2, 2025 | Guidewire Software, Inc. | $GWRE | Rosenbaum Michael George | Chief Executive Officer | S | Common Stock | 1400 | $214.30 | 223,268.0000 | 85,911,653 | 0.62% | 0.00% |
| Aug. 25, 2025 | Guidewire Software, Inc. | $GWRE | Rosenbaum Michael George | Chief Executive Officer | S | Common Stock | 1400 | $214.70 | 224,668.0000 | 85,911,653 | 0.62% | 0.00% |
| Aug. 18, 2025 | Guidewire Software, Inc. | $GWRE | Rosenbaum Michael George | Chief Executive Officer | S | Common Stock | 1400 | $211.61 | 226,068.0000 | 85,911,653 | 0.62% | 0.00% |
| Aug. 11, 2025 | Guidewire Software, Inc. | $GWRE | Rosenbaum Michael George | Chief Executive Officer | S | Common Stock | 1400 | $212.44 | 227,468.0000 | 85,911,653 | 0.61% | 0.00% |
| Aug. 4, 2025 | Guidewire Software, Inc. | $GWRE | Rosenbaum Michael George | Chief Executive Officer | S | Common Stock | 1400 | $225.04 | 228,868.0000 | 85,911,653 | 0.61% | 0.00% |
| July 28, 2025 | Guidewire Software, Inc. | $GWRE | Rosenbaum Michael George | Chief Executive Officer | S | Common Stock | 1400 | $223.75 | 230,268.0000 | 85,960,868 | 0.60% | 0.00% |
| July 21, 2025 | Guidewire Software, Inc. | $GWRE | Rosenbaum Michael George | Chief Executive Officer | S | Common Stock | 1400 | $222.31 | 231,668.0000 | 85,960,868 | 0.60% | 0.00% |
| July 14, 2025 | Guidewire Software, Inc. | $GWRE | Rosenbaum Michael George | Chief Executive Officer | S | Common Stock | 1400 | $220.65 | 233,068.0000 | 85,960,868 | 0.60% | 0.00% |
| July 7, 2025 | Guidewire Software, Inc. | $GWRE | Rosenbaum Michael George | Chief Executive Officer | S | Common Stock | 1400 | $230.70 | 234,468.0000 | 85,960,868 | 0.59% | 0.00% |
| June 30, 2025 | Guidewire Software, Inc. | $GWRE | Rosenbaum Michael George | Chief Executive Officer | S | Common Stock | 1400 | $236.89 | 235,868.0000 | 85,960,868 | 0.59% | 0.00% |
| June 23, 2025 | Guidewire Software, Inc. | $GWRE | Rosenbaum Michael George | Chief Executive Officer | S | Common Stock | 1400 | $238.12 | 237,268.0000 | 85,960,868 | 0.59% | 0.00% |
| June 16, 2025 | Guidewire Software, Inc. | $GWRE | Rosenbaum Michael George | Chief Executive Officer | S | Common Stock | 1400 | $254.53 | 244,593.0000 | 85,960,868 | 0.57% | 0.00% |
| June 17, 2025 | Guidewire Software, Inc. | $GWRE | Rosenbaum Michael George | Chief Executive Officer | S | Common Stock | 5925 | $248.94 | 238,668.0000 | 85,960,868 | 2.42% | 0.01% |
| June 9, 2025 | Guidewire Software, Inc. | $GWRE | Rosenbaum Michael George | Chief Executive Officer | S | Common Stock | 1400 | $256.50 | 245,993.0000 | 85,960,868 | 0.57% | 0.00% |
| June 2, 2025 | Guidewire Software, Inc. | $GWRE | Rosenbaum Michael George | Chief Executive Officer | S | Common Stock | 1400 | $215.35 | 247,393.0000 | 85,960,868 | 0.56% | 0.00% |
| May 27, 2025 | Guidewire Software, Inc. | $GWRE | Rosenbaum Michael George | Chief Executive Officer | S | Common Stock | 1400 | $212.02 | 248,793.0000 | 85,960,868 | 0.56% | 0.00% |
| May 19, 2025 | Guidewire Software, Inc. | $GWRE | Rosenbaum Michael George | Chief Executive Officer | S | Common Stock | 1400 | $215.25 | 250,193.0000 | 85,960,868 | 0.56% | 0.00% |
| May 12, 2025 | Guidewire Software, Inc. | $GWRE | Rosenbaum Michael George | Chief Executive Officer | S | Common Stock | 1400 | $216.51 | 251,593.0000 | 85,960,868 | 0.55% | 0.00% |
| May 5, 2025 | Guidewire Software, Inc. | $GWRE | Rosenbaum Michael George | Chief Executive Officer | S | Common Stock | 1400 | $208.36 | 252,993.0000 | 85,960,868 | 0.55% | 0.00% |
| April 28, 2025 | Guidewire Software, Inc. | $GWRE | Rosenbaum Michael George | Chief Executive Officer | S | Common Stock | 1400 | $198.22 | 254,393.0000 | 85,960,868 | 0.55% | 0.00% |
| April 21, 2025 | Guidewire Software, Inc. | $GWRE | Rosenbaum Michael George | Chief Executive Officer | S | Common Stock | 1400 | $189.44 | 255,793.0000 | 85,960,868 | 0.54% | 0.00% |
| April 14, 2025 | Guidewire Software, Inc. | $GWRE | Rosenbaum Michael George | Chief Executive Officer | S | Common Stock | 1400 | $194.90 | 257,193.0000 | 85,960,868 | 0.54% | 0.00% |
| April 7, 2025 | Guidewire Software, Inc. | $GWRE | Rosenbaum Michael George | Chief Executive Officer | S | Common Stock | 1400 | $167.82 | 258,593.0000 | 85,960,868 | 0.54% | 0.00% |
| March 31, 2025 | Guidewire Software, Inc. | $GWRE | Rosenbaum Michael George | Chief Executive Officer | S | Common Stock | 1400 | $184.41 | 259,993.0000 | 85,960,868 | 0.54% | 0.00% |
| March 24, 2025 | Guidewire Software, Inc. | $GWRE | Rosenbaum Michael George | Chief Executive Officer | S | Common Stock | 1400 | $195.15 | 261,393.0000 | 85,960,868 | 0.53% | 0.00% |
| March 17, 2025 | Guidewire Software, Inc. | $GWRE | Rosenbaum Michael George | Chief Executive Officer | S | Common Stock | 1400 | $185.03 | 267,730.0000 | 85,960,868 | 0.52% | 0.00% |
| March 18, 2025 | Guidewire Software, Inc. | $GWRE | Rosenbaum Michael George | Chief Executive Officer | S | Common Stock | 4937 | $189.41 | 262,793.0000 | 85,960,868 | 1.84% | 0.01% |
| March 10, 2025 | Guidewire Software, Inc. | $GWRE | Rosenbaum Michael George | Chief Executive Officer | S | Common Stock | 1400 | $170.04 | 269,130.0000 | 85,960,868 | 0.52% | 0.00% |
| March 3, 2025 | Guidewire Software, Inc. | $GWRE | Rosenbaum Michael George | Chief Executive Officer | S | Common Stock | 1400 | $203.13 | 270,530.0000 | 85,960,868 | 0.51% | 0.00% |
| Feb. 24, 2025 | Guidewire Software, Inc. | $GWRE | Rosenbaum Michael George | Chief Executive Officer | S | Common Stock | 1400 | $203.65 | 271,930.0000 | 85,960,868 | 0.51% | 0.00% |
| Feb. 18, 2025 | Guidewire Software, Inc. | $GWRE | Rosenbaum Michael George | Chief Executive Officer | S | Common Stock | 1400 | $212.42 | 273,330.0000 | 85,960,868 | 0.51% | 0.00% |
| Feb. 10, 2025 | Guidewire Software, Inc. | $GWRE | Rosenbaum Michael George | Chief Executive Officer | S | Common Stock | 1400 | $214.68 | 274,730.0000 | 85,960,868 | 0.51% | 0.00% |
| Feb. 3, 2025 | Guidewire Software, Inc. | $GWRE | Rosenbaum Michael George | Chief Executive Officer | S | Common Stock | 1400 | $208.42 | 276,130.0000 | 85,960,868 | 0.50% | 0.00% |
| Jan. 27, 2025 | Guidewire Software, Inc. | $GWRE | Rosenbaum Michael George | Chief Executive Officer | S | Common Stock | 1400 | $201.90 | 277,530.0000 | 85,960,868 | 0.50% | 0.00% |
| Jan. 21, 2025 | Guidewire Software, Inc. | $GWRE | Rosenbaum Michael George | Chief Executive Officer | S | Common Stock | 1400 | $179.91 | 278,930.0000 | 85,960,868 | 0.50% | 0.00% |
| Jan. 15, 2025 | Guidewire Software, Inc. | $GWRE | Rosenbaum Michael George | Chief Executive Officer | S | Common Stock | 1400 | $174.78 | 280,330.0000 | 85,960,868 | 0.50% | 0.00% |
| Dec. 17, 2024 | Guidewire Software, Inc. | $GWRE | Rosenbaum Michael George | Chief Executive Officer | S | Common Stock | 5932 | $171.06 | 281,730.0000 | 85,960,868 | 2.06% | 0.01% |
| Sept. 17, 2024 | Guidewire Software, Inc. | $GWRE | Rosenbaum Michael George | Chief Executive Officer | S | Common Stock | 23379 | $172.16 | 287,662.0000 | 82,291,483 | 7.52% | 0.03% |
| Sept. 15, 2024 | Guidewire Software, Inc. | $GWRE | Rosenbaum Michael George | Chief Executive Officer | M | Performance Shares | 24608 | $0.00 | 0.0000 | 82,291,483 | 100.00% | 0.03% |
| Sept. 15, 2024 | Guidewire Software, Inc. | $GWRE | Rosenbaum Michael George | Chief Executive Officer | M | Common Stock | 24608 | $0.00 | 300,934.0000 | 82,291,483 | 8.91% | 0.03% |
| Sept. 15, 2024 | Guidewire Software, Inc. | $GWRE | Rosenbaum Michael George | Chief Executive Officer | M | Common Stock | 10107 | $0.00 | 311,041.0000 | 82,291,483 | 3.36% | 0.01% |
| Sept. 15, 2024 | Guidewire Software, Inc. | $GWRE | Rosenbaum Michael George | Chief Executive Officer | M | Performance Shares | 10107 | $0.00 | 39,892.0000 | 82,291,483 | 20.21% | 0.01% |
| Sept. 11, 2024 | Guidewire Software, Inc. | $GWRE | Rosenbaum Michael George | Chief Executive Officer | A | Common Stock | 36533 | $0.00 | 276,326.0000 | 82,291,483 | 15.24% | 0.04% |
| Sept. 11, 2024 | Guidewire Software, Inc. | $GWRE | Rosenbaum Michael George | Chief Executive Officer | A | Performance Shares | 36533 | $0.00 | 36,533.0000 | 82,291,483 | 9999.99% | 0.04% |
| June 18, 2024 | Guidewire Software, Inc. | $GWRE | Rosenbaum Michael George | Chief Executive Officer | S | Common Stock | 5582 | $134.54 | 239,793.0000 | 82,176,629 | 2.27% | 0.01% |
| March 19, 2024 | Guidewire Software, Inc. | $GWRE | Rosenbaum Michael George | Chief Executive Officer | S | Common Stock | 4420 | $111.75 | 245,375.0000 | 82,176,629 | 1.77% | 0.01% |