Guidewire Software Inc
NYSE: GWRE · TECHNOLOGY · SOFTWARE - APPLICATION
Updated 2026-06-05
Guidewire Software Inc (GWRE) Insider transactions
All transactions
| Date | Insider | Title | Type | Shares | Price | Value |
|---|---|---|---|---|---|---|
| 2026-06-01 | ROSENBAUM, MICHAEL GEORGE | Director, Chief Executive Officer | Sale | 1,200 | $158.92 | $190704.00 |
| 2026-05-26 | ROSENBAUM, MICHAEL GEORGE | Director, Chief Executive Officer | Sale | 1,200 | $138.51 | $166212.00 |
| 2026-05-18 | ROSENBAUM, MICHAEL GEORGE | Director, Chief Executive Officer | Sale | 1,200 | $128.19 | $153828.00 |
| 2026-05-11 | ROSENBAUM, MICHAEL GEORGE | Director, Chief Executive Officer | Sale | 1,200 | $136.38 | $163656.00 |
| 2026-05-04 | ROSENBAUM, MICHAEL GEORGE | Director, Chief Executive Officer | Sale | 1,200 | $141.91 | $170292.00 |
| 2026-04-27 | ROSENBAUM, MICHAEL GEORGE | Director, Chief Executive Officer | Sale | 1,200 | $138.09 | $165708.00 |
| 2026-04-20 | ROSENBAUM, MICHAEL GEORGE | Director, Chief Executive Officer | Sale | 1,200 | $139.75 | $167700.00 |
| 2026-04-13 | ROSENBAUM, MICHAEL GEORGE | Director, Chief Executive Officer | Sale | 1,200 | $118.77 | $142524.00 |
| 2026-04-06 | ROSENBAUM, MICHAEL GEORGE | Director, Chief Executive Officer | Sale | 1,200 | $151.14 | $181368.00 |
| 2026-03-30 | ROSENBAUM, MICHAEL GEORGE | Director, Chief Executive Officer | Sale | 1,200 | $145.74 | $174888.00 |
| 2026-03-23 | ROSENBAUM, MICHAEL GEORGE | Director, Chief Executive Officer | Sale | 1,200 | $155.56 | $186672.00 |
| 2026-03-17 | ROSENBAUM, MICHAEL GEORGE | Director, Chief Executive Officer | Sale | 4,737 | $163.86 | $776194.87 |
| 2026-03-17 | PETERSON, DAVID FRANKLIN | Chief Accounting Officer | Sale | 273 | $163.86 | $44733.21 |
| 2026-03-17 | MULLEN, JOHN P | President | Sale | 6,576 | $163.86 | $1.08M |
| 2026-03-17 | KING, JAMES WINSTON | Chief Admin Officer, Gen Couns | Sale | 1,001 | $163.86 | $164021.76 |
| 2026-03-17 | COOPER, JEFFREY ELLIOTT | Chief Financial Officer | Sale | 1,935 | $163.86 | $317065.04 |
| 2026-03-16 | ROSENBAUM, MICHAEL GEORGE | Director, Chief Executive Officer | Sale | 1,200 | $160.00 | $192000.00 |
| 2026-03-13 | COOPER, JEFFREY ELLIOTT | Chief Financial Officer | Sale | 4,757 | $158.72 | $755031.04 |
| 2026-03-09 | ROSENBAUM, MICHAEL GEORGE | Director, Chief Executive Officer | Sale | 1,200 | $166.34 | $199608.00 |
| 2026-03-02 | ROSENBAUM, MICHAEL GEORGE | Director, Chief Executive Officer | Sale | 1,200 | $143.87 | $172644.00 |
| 2026-02-23 | ROSENBAUM, MICHAEL GEORGE | Director, Chief Executive Officer | Sale | 1,200 | $125.50 | $150600.00 |
| 2026-02-17 | ROSENBAUM, MICHAEL GEORGE | Director, Chief Executive Officer | Sale | 1,200 | $127.00 | $152400.00 |
| 2026-02-09 | ROSENBAUM, MICHAEL GEORGE | Director, Chief Executive Officer | Sale | 1,200 | $127.77 | $153324.00 |
| 2026-02-02 | ROSENBAUM, MICHAEL GEORGE | Director, Chief Executive Officer | Sale | 1,200 | $140.01 | $168012.00 |
| 2026-01-26 | ROSENBAUM, MICHAEL GEORGE | Director, Chief Executive Officer | Sale | 1,200 | $160.32 | $192384.00 |
| 2026-01-20 | ROSENBAUM, MICHAEL GEORGE | Director, Chief Executive Officer | Sale | 1,200 | $156.26 | $187512.00 |
| 2026-01-13 | ROSENBAUM, MICHAEL GEORGE | Director, Chief Executive Officer | Sale | 1,200 | $180.87 | $217044.00 |
| 2026-01-13 | COOPER, JEFFREY ELLIOTT | Chief Financial Officer | Sale | 216 | $180.87 | $39067.92 |
| 2025-12-29 | ROSENBAUM, MICHAEL GEORGE | Director, Chief Executive Officer | Sale | 1,400 | $204.95 | $286930.00 |
| 2025-12-22 | ROSENBAUM, MICHAEL GEORGE | Director, Chief Executive Officer | Sale | 1,400 | $200.72 | $281008.00 |
| 2025-12-18 | KING, JAMES WINSTON | Chief Admin Officer, Gen Couns | Sale | 1,860 | $195.00 | $362700.00 |
| 2025-12-18 | COOPER, JEFFREY ELLIOTT | Chief Financial Officer | Sale | 1,232 | $195.00 | $240240.00 |
| 2025-12-16 | ROSENBAUM, MICHAEL GEORGE | Director, Chief Executive Officer | Sale | 6,015 | $192.08 | $1.16M |
| 2025-12-16 | PETERSON, DAVID FRANKLIN | Chief Accounting Officer | Sale | 358 | $192.08 | $68763.24 |
| 2025-12-16 | MULLEN, JOHN P | President | Sale | 7,975 | $192.08 | $1.53M |
| 2025-12-16 | KING, JAMES WINSTON | Chief Admin Officer, Gen Couns | Sale | 1,457 | $192.08 | $279854.88 |
| 2025-12-16 | COOPER, JEFFREY ELLIOTT | Chief Financial Officer | Sale | 2,872 | $192.08 | $551642.56 |
| 2025-12-15 | SLOAN, JEFFREY STEVEN | Director | Buy | 1,196 | — | — |
| 2025-12-15 | ROSENBAUM, MICHAEL GEORGE | Director, Chief Executive Officer | Sale | 1,400 | $204.34 | $286076.00 |
| 2025-12-15 | RAMANATHAN, RAJANI | Director | Buy | 1,196 | — | — |
| 2025-12-15 | LEGO, CATHERINE P | Director | Buy | 1,196 | — | — |
| 2025-12-15 | KELLER, MICHAEL C | Director | Buy | 1,196 | — | — |
| 2025-12-15 | DILLON, MARGARET | Director | Buy | 1,196 | — | — |
| 2025-12-15 | BAUER, DAVID S | Director | Buy | 1,196 | — | — |
| 2025-12-15 | ANQUILLARE, MARK V | Director | Buy | 1,196 | — | — |
| 2025-12-08 | ROSENBAUM, MICHAEL GEORGE | Director, Chief Executive Officer | Sale | 1,400 | $210.87 | $295218.00 |
| 2025-12-01 | ROSENBAUM, MICHAEL GEORGE | Director, Chief Executive Officer | Sale | 1,400 | $213.44 | $298816.00 |
| 2025-12-01 | MULLEN, JOHN P | President | Sale | 3,000 | $213.44 | $640320.00 |
| 2025-11-24 | ROSENBAUM, MICHAEL GEORGE | Director, Chief Executive Officer | Sale | 1,400 | $213.23 | $298522.00 |
| 2025-11-17 | ROSENBAUM, MICHAEL GEORGE | Director, Chief Executive Officer | Sale | 1,400 | $222.54 | $311556.00 |
| 2025-11-17 | KING, JAMES WINSTON | Chief Admin Officer, Gen Couns | Sale | 798 | $222.54 | $177586.92 |
| 2025-11-10 | ROSENBAUM, MICHAEL GEORGE | Director, Chief Executive Officer | Sale | 1,400 | $218.53 | $305942.00 |
| 2025-11-03 | ROSENBAUM, MICHAEL GEORGE | Director, Chief Executive Officer | Sale | 1,400 | $231.85 | $324590.00 |
| 2025-11-03 | MULLEN, JOHN P | President | Sale | 3,000 | $231.85 | $695550.00 |
| 2025-10-27 | ROSENBAUM, MICHAEL GEORGE | Director, Chief Executive Officer | Sale | 1,400 | $255.40 | $357560.00 |
| 2025-10-20 | ROSENBAUM, MICHAEL GEORGE | Director, Chief Executive Officer | Sale | 1,400 | $245.70 | $343980.00 |
| 2025-10-20 | KING, JAMES WINSTON | Chief Admin Officer, Gen Couns | Sale | 798 | $245.70 | $196068.60 |
| 2025-10-13 | ROSENBAUM, MICHAEL GEORGE | Director, Chief Executive Officer | Sale | 1,400 | $239.71 | $335594.00 |
| 2025-10-06 | ROSENBAUM, MICHAEL GEORGE | Director, Chief Executive Officer | Sale | 1,400 | $230.08 | $322112.00 |
| 2025-10-01 | MULLEN, JOHN P | President | Sale | 3,000 | $230.73 | $692190.00 |
| 2025-10-01 | BAUER, DAVID S | Director | Sale | 500 | $230.73 | $115365.00 |
| 2025-09-29 | ROSENBAUM, MICHAEL GEORGE | Director, Chief Executive Officer | Sale | 1,400 | $232.25 | $325150.00 |
| 2025-09-24 | COOPER, JEFFREY ELLIOTT | Chief Financial Officer | Sale | 38 | — | — |
| 2025-09-22 | ROSENBAUM, MICHAEL GEORGE | Director, Chief Executive Officer | Sale | 1,400 | $244.55 | $342370.00 |
| 2025-09-18 | PETERSON, DAVID FRANKLIN | Chief Accounting Officer | Sale | 1,000 | $249.86 | $249860.00 |
| 2025-09-18 | KING, JAMES WINSTON | Chief Admin Officer, Gen Couns | Sale | 2,147 | $250.12 | $537013.22 |
| 2025-09-18 | KING, JAMES WINSTON | Chief Admin Officer, Gen Couns | Sale | 1,940 | $249.35 | $483745.79 |
| 2025-09-18 | KING, JAMES WINSTON | Chief Admin Officer, Gen Couns | Sale | 1,878 | $247.21 | $464258.50 |
| 2025-09-18 | KING, JAMES WINSTON | Chief Admin Officer, Gen Couns | Sale | 1,197 | $248.16 | $297041.89 |
| 2025-09-18 | COOPER, JEFFREY ELLIOTT | Chief Financial Officer | Sale | 2,480 | $249.75 | $619384.46 |
| 2025-09-18 | COOPER, JEFFREY ELLIOTT | Chief Financial Officer | Sale | 1,876 | $248.64 | $466450.33 |
| 2025-09-18 | COOPER, JEFFREY ELLIOTT | Chief Financial Officer | Sale | 1,461 | $247.47 | $361560.10 |
| 2025-09-18 | COOPER, JEFFREY ELLIOTT | Chief Financial Officer | Sale | 860 | $246.80 | $212246.11 |
| 2025-09-18 | COOPER, JEFFREY ELLIOTT | Chief Financial Officer | Sale | 858 | $250.28 | $214736.21 |
| 2025-09-16 | ROSENBAUM, MICHAEL GEORGE | Director, Chief Executive Officer | Sale | 30,317 | $242.87 | $7.36M |
| 2025-09-16 | PETERSON, DAVID FRANKLIN | Chief Accounting Officer | Sale | 1,811 | $242.87 | $439833.04 |
| 2025-09-16 | MULLEN, JOHN P | President | Sale | 15,869 | $242.87 | $3.85M |
| 2025-09-16 | KING, JAMES WINSTON | Chief Admin Officer, Gen Couns | Sale | 7,149 | $242.87 | $1.74M |
| 2025-09-16 | COOPER, JEFFREY ELLIOTT | Chief Financial Officer | Sale | 14,103 | $242.87 | $3.43M |
| 2025-09-15 | ROSENBAUM, MICHAEL GEORGE | Director, Chief Executive Officer | Sale | 45,849 | — | — |
| 2025-09-15 | ROSENBAUM, MICHAEL GEORGE | Director, Chief Executive Officer | Buy | 45,849 | — | — |
| 2025-09-15 | ROSENBAUM, MICHAEL GEORGE | Director, Chief Executive Officer | Sale | 1,400 | $252.83 | $353962.00 |
| 2025-09-15 | PETERSON, DAVID FRANKLIN | Chief Accounting Officer | Sale | 3,179 | — | — |
| 2025-09-15 | PETERSON, DAVID FRANKLIN | Chief Accounting Officer | Buy | 3,179 | — | — |
| 2025-09-15 | MULLEN, JOHN P | President | Sale | 18,543 | — | — |
| 2025-09-15 | MULLEN, JOHN P | President | Buy | 18,543 | — | — |
| 2025-09-15 | KING, JAMES WINSTON | Chief Admin Officer, Gen Couns | Sale | 10,597 | — | — |
| 2025-09-15 | KING, JAMES WINSTON | Chief Admin Officer, Gen Couns | Buy | 10,597 | — | — |
| 2025-09-15 | COOPER, JEFFREY ELLIOTT | Chief Financial Officer | Sale | 21,194 | — | — |
| 2025-09-15 | COOPER, JEFFREY ELLIOTT | Chief Financial Officer | Buy | 21,194 | — | — |
| 2025-09-11 | ROSENBAUM, MICHAEL GEORGE | Director, Chief Executive Officer | Buy | 28,958 | — | — |
| 2025-09-11 | ROSENBAUM, MICHAEL GEORGE | Director, Chief Executive Officer | Buy | 28,958 | — | — |
| 2025-09-11 | PETERSON, DAVID FRANKLIN | Chief Accounting Officer | Buy | 843 | — | — |
| 2025-09-11 | MULLEN, JOHN P | President | Buy | 15,795 | — | — |
| 2025-09-11 | MULLEN, JOHN P | President | Buy | 15,795 | — | — |
| 2025-09-11 | KING, JAMES WINSTON | Chief Admin Officer, Gen Couns | Buy | 5,687 | — | — |
| 2025-09-11 | KING, JAMES WINSTON | Chief Admin Officer, Gen Couns | Buy | 5,687 | — | — |
| 2025-09-11 | COOPER, JEFFREY ELLIOTT | Chief Financial Officer | Buy | 12,636 | — | — |
| 2025-09-11 | COOPER, JEFFREY ELLIOTT | Chief Financial Officer | Buy | 12,636 | — | — |
| 2025-09-08 | ROSENBAUM, MICHAEL GEORGE | Director, Chief Executive Officer | Sale | 1,400 | $261.28 | $365792.00 |
Frequently asked questions
Are GWRE insiders buying or selling?
Over the transactions on record, GWRE insiders have been net sellers, with about $39.69M in stock sold across 79 sales. The entries tagged as buys are stock grants and option exercises recorded at $0, not open-market purchases.
Does insider selling at GWRE mean the stock will fall?
Not by itself. Most executive selling is pre-scheduled through 10b5-1 plans filed months in advance, and insiders sell for diversification, taxes, and liquidity far more often than out of any view on the price. Insider buying is the stronger signal, especially when several insiders buy around the same time, because there is usually only one reason to put personal cash into the stock.
Which GWRE insiders are selling the most?
Recent selling is concentrated in a few names. ROSENBAUM, MICHAEL GEORGE accounts for the largest share on record, with about $18.38M sold. Selling by one or two individuals matters less than broad selling across the whole leadership team, which is the pattern worth watching.