There have been 50 recent insider transactions recorded for Guidewire Software, Inc. (GWRE), including 7 buys and 43 sells. Total insider buying was valued at RSU Award and total insider selling at $15.13M.
Notable insiders with recent activity include Rosenbaum Michael George, Peterson David Franklin, King James Winston. Insider transactions can provide insights into how company leadership views the stock's valuation and future prospects.
Insider Transactions — GWRE
| Date |
Name |
Role |
Transaction |
Shares |
Avg. Price |
Value |
Shares Owned |
| 2026-04-06 |
Rosenbaum Michael George |
Chief Executive Officer |
Informative Sell |
1,200 |
$151.14 |
$181.37K |
217,606 |
| 2026-03-30 |
Rosenbaum Michael George |
Chief Executive Officer |
Informative Sell |
1,200 |
$145.74 |
$174.89K |
218,806 |
| 2026-03-23 |
Rosenbaum Michael George |
Chief Executive Officer |
Informative Sell |
1,200 |
$155.56 |
$186.67K |
220,006 |
| 2026-03-17 |
Peterson David Franklin |
Chief Accounting Officer |
Informative Sell |
273 |
$163.86 |
$44.73K |
12,533 |
| 2026-03-17 |
King James Winston |
Chief Admin Officer, Gen Couns |
Informative Sell |
1,001 |
$163.86 |
$164.02K |
32,701 |
| 2026-03-17 |
Rosenbaum Michael George |
Chief Executive Officer |
Informative Sell |
4,737 |
$163.86 |
$776.2K |
221,206 |
| 2026-03-17 |
Cooper Jeffrey Elliott |
Chief Financial Officer |
Informative Sell |
1,935 |
$163.86 |
$317.07K |
66,061 |
| 2026-03-17 |
Mullen John P |
President |
Informative Sell |
6,576 |
$163.86 |
$1.08M |
135,407 |
| 2026-03-16 |
Rosenbaum Michael George |
Chief Executive Officer |
Informative Sell |
1,200 |
$160.00 |
$192K |
225,943 |
| 2026-03-13 |
Cooper Jeffrey Elliott |
Chief Financial Officer |
Informative Sell |
4,757 |
$158.72 |
$755.03K |
67,996 |
| 2026-03-09 |
Rosenbaum Michael George |
Chief Executive Officer |
Informative Sell |
1,200 |
$166.34 |
$199.61K |
227,143 |
| 2026-03-02 |
Rosenbaum Michael George |
Chief Executive Officer |
Informative Sell |
1,200 |
$143.87 |
$172.64K |
228,343 |
| 2026-02-23 |
Rosenbaum Michael George |
Chief Executive Officer |
Informative Sell |
1,200 |
$125.50 |
$150.6K |
229,543 |
| 2026-02-17 |
Rosenbaum Michael George |
Chief Executive Officer |
Informative Sell |
1,200 |
$127.00 |
$152.4K |
230,743 |
| 2026-02-09 |
Rosenbaum Michael George |
Chief Executive Officer |
Informative Sell |
1,200 |
$127.77 |
$153.32K |
231,943 |
| 2026-02-02 |
Rosenbaum Michael George |
Chief Executive Officer |
Informative Sell |
1,200 |
$140.01 |
$168.01K |
233,143 |
| 2026-01-26 |
Rosenbaum Michael George |
Chief Executive Officer |
Informative Sell |
1,200 |
$160.32 |
$192.38K |
234,343 |
| 2026-01-20 |
Rosenbaum Michael George |
Chief Executive Officer |
Informative Sell |
1,200 |
$156.26 |
$187.51K |
235,543 |
| 2026-01-13 |
Rosenbaum Michael George |
Chief Executive Officer |
Informative Sell |
1,200 |
$180.87 |
$217.04K |
236,743 |
| 2026-01-13 |
Cooper Jeffrey Elliott |
Chief Financial Officer |
Informative Sell |
216 |
$180.87 |
$39.07K |
72,753 |
| 2025-12-29 |
Rosenbaum Michael George |
Chief Executive Officer |
Informative Sell |
1,400 |
$204.95 |
$286.93K |
237,943 |
| 2025-12-22 |
Rosenbaum Michael George |
Chief Executive Officer |
Informative Sell |
1,400 |
$200.72 |
$281.01K |
239,343 |
| 2025-12-18 |
King James Winston |
Chief Admin Officer, Gen Couns |
Informative Sell |
1,860 |
$195.00 |
$362.7K |
33,702 |
| 2025-12-18 |
Cooper Jeffrey Elliott |
Chief Financial Officer |
Informative Sell |
1,232 |
$195.00 |
$240.24K |
72,969 |
| 2025-12-16 |
Peterson David Franklin |
Chief Accounting Officer |
Informative Sell |
358 |
$192.08 |
$68.76K |
12,806 |
| 2025-12-16 |
Rosenbaum Michael George |
Chief Executive Officer |
Informative Sell |
6,015 |
$192.08 |
$1.16M |
240,743 |
| 2025-12-16 |
Mullen John P |
President |
Informative Sell |
7,975 |
$192.08 |
$1.53M |
141,983 |
| 2025-12-16 |
King James Winston |
Chief Admin Officer, Gen Couns |
Informative Sell |
1,457 |
$192.08 |
$279.85K |
35,562 |
| 2025-12-16 |
Cooper Jeffrey Elliott |
Chief Financial Officer |
Informative Sell |
2,872 |
$192.08 |
$551.64K |
74,201 |
| 2025-12-15 |
Rosenbaum Michael George |
Chief Executive Officer |
Informative Sell |
1,400 |
$204.34 |
$286.08K |
246,758 |
| 2025-12-15 |
Keller Michael C |
Director |
RSU Award |
1,196 |
- |
- |
10,606 |
| 2025-12-15 |
Lego Catherine P |
Director |
RSU Award |
1,196 |
- |
- |
14,393 |
| 2025-12-15 |
Anquillare Mark V |
Director |
RSU Award |
1,196 |
- |
- |
2,716 |
| 2025-12-15 |
Sloan Jeffrey Steven |
Director |
RSU Award |
1,196 |
- |
- |
2,371 |
| 2025-12-15 |
Dillon Margaret |
Director |
RSU Award |
1,196 |
- |
- |
16,393 |
| 2025-12-15 |
Ramanathan Rajani |
Director |
RSU Award |
1,196 |
- |
- |
11,057 |
| 2025-12-15 |
Bauer David S |
Director |
RSU Award |
1,196 |
- |
- |
7,099 |
| 2025-12-08 |
Rosenbaum Michael George |
Chief Executive Officer |
Informative Sell |
1,400 |
$210.87 |
$295.22K |
248,158 |
| 2025-12-01 |
Rosenbaum Michael George |
Chief Executive Officer |
Informative Sell |
1,400 |
$213.44 |
$298.82K |
249,558 |
| 2025-12-01 |
Mullen John P |
President |
Informative Sell |
3,000 |
$213.44 |
$640.32K |
149,958 |
| 2025-11-24 |
Rosenbaum Michael George |
Chief Executive Officer |
Informative Sell |
1,400 |
$213.23 |
$298.52K |
250,958 |
| 2025-11-17 |
King James Winston |
Chief Admin Officer, Gen Couns |
Informative Sell |
798 |
$222.54 |
$177.59K |
37,019 |
| 2025-11-17 |
Rosenbaum Michael George |
Chief Executive Officer |
Informative Sell |
1,400 |
$222.54 |
$311.56K |
252,358 |
| 2025-11-10 |
Rosenbaum Michael George |
Chief Executive Officer |
Informative Sell |
1,400 |
$218.53 |
$305.94K |
253,758 |
| 2025-11-03 |
Rosenbaum Michael George |
Chief Executive Officer |
Informative Sell |
1,400 |
$231.85 |
$324.59K |
255,158 |
| 2025-11-03 |
Mullen John P |
President |
Informative Sell |
3,000 |
$231.85 |
$695.55K |
152,958 |
| 2025-10-27 |
Rosenbaum Michael George |
Chief Executive Officer |
Informative Sell |
1,400 |
$255.40 |
$357.56K |
256,558 |
| 2025-10-20 |
King James Winston |
Chief Admin Officer, Gen Couns |
Informative Sell |
798 |
$245.70 |
$196.07K |
37,817 |
| 2025-10-20 |
Rosenbaum Michael George |
Chief Executive Officer |
Informative Sell |
1,400 |
$245.70 |
$343.98K |
257,958 |
| 2025-10-13 |
Rosenbaum Michael George |
Chief Executive Officer |
Informative Sell |
1,400 |
$239.71 |
$335.59K |
259,358 |
■ Informative Buy/Sell — open market transaction (most significant)
■ Uninformative Buy — award, option exercise, conversion
■ Uninformative Sell — tax withholding, award vest sale
■ Neutral — gift, trust, expiry
