Michael George Rosenbaum

GWRE CEO sells 7,030 shares for $840,891.69 under 10b5-1 plan; stock -56.9% from high, -26.2% over 90 days.

Michael George Rosenbaum, who was CEO at the time of filing, executed two separate sales totaling 7,030 shares for $840,891.69 on June 15–16, 2026, as part of a pre-arranged 10b5-1 trading plan adopted on 2025-10-14. The blended average sale price of $119.61 occurs in a period when the stock trades at $117.46 (current price) and stands -56.9% from its 52-week high of $272.60, with a 90-day decline of -26.2%. At GWRE specifically, the insider's prior five sales have all followed negative 30-day patterns (-15.1%, -13.5%, +0.4%, -11.2%, -13.5%), and four of five showed negative 90-day returns, suggesting the stock often declines after his scheduled sells. This scheduled plan execution warrants attention given the stock's steep recent loss and the historical pattern of post-sale weakness at this ticker, though fundamental metrics (revenue growth +22.6%, $9.8B market cap) remain intact.

CEO Michael George Rosenbaum sells 4,737 GWRE shares at $163.86; stock now $159.27, -39.2% from 52-week high.

Rosenbaum sold 4,737 shares (4.7K shares) for $776,194.87 ($776.2K) at $163.86 on 2026-03-17, reducing his stake from 225,943 shares (225.9K shares) to 221,206 shares (221.2K shares), a -2.1% net reduction. The current price of $159.27 is -39.2% from the 52-week high of $261.88, and the stock has declined -19.3% over 90 days despite a +25.4% 30-day bounce. His prior trades at GWRE show mixed timing results: 3 of 5 prior sells were well-timed at the 90-day mark, but the most recent sale on 2025-12-16 had a -13.5% 30-day return and the sale on 2025-03-18 was followed by a +33.9% 90-day gain, suggesting inconsistent predictive value. The company's fundamentals show strong revenue growth of +22.6% year-over-year and positive net income of $60,110,000.00 ($60.1M) on revenue of $359,095,000.00 ($359.1M), though the P/E of 71.10 reflects elevated valuation expectations relative to current earnings.

CEO Rosenbaum sold 6,015 shares of GWRE at $192.08 on 2025-12-16 for $1,155,337.74; stock down 26.0% from 52-week high.

Michael George Rosenbaum, CEO of Guidewire Software, sold 6,015 shares (6.0K shares) at $192.08 on 2025-12-16, reducing his holdings by 2.4% to 240,743 shares. The sale occurred as GWRE trades 26.0% below its 52-week high of $261.88 and has declined 21.4% over the past 90 days. Historically, Rosenbaum's cross-ticker track record shows a 90-day well-timed rate of 27.27% across 11 prior sells; however, at GWRE specifically, only 2 of 5 prior sells were well-timed at the 90-day mark, suggesting inconsistent predictive value at this ticker. The current sale occurs against a backdrop of strong fundamentals—revenue of $332,639,000.00 in the latest quarter, net income of $31,308,000.00, and 22.6% annual revenue growth—yet the elevated P/E of 179.56 reflects the market's pricing in of future growth expectations that stock performance has recently failed to deliver.

CEO Michael Rosenbaum sells 30,317 shares of GWRE for $7.4M at $242.87; holds 264,958 shares post-transaction.

CEO Rosenbaum sold 30,317 shares at $242.87, representing a -10.3% reduction from his 295,275 pre-transaction holdings. The sale occurred when GWRE traded at $242.87, approximately 5.7% below its 52-week high of $261.88, though the stock has surged 14.8% over the prior 30 days. Rosenbaum's prior trades at GWRE show mixed timing: his most recent pair of sales in June 2025 were followed by 30-day declines of -11.2% and -13.5%, but his earlier sales in March and December 2025 saw the stock rise substantially, with 90-day returns of +33.9% and +36.8%. This sale represents a substantial reduction in absolute share count from a CEO with significant holdings, but the insider retains 264,958 shares and the transaction occurs at a price near but not at the 52-week peak.

CEO Michael Rosenbaum sold 7,325 shares of GWRE for $1,831,299.65 across two trades on 2025-06-16 and 2025-06-17.

Michael Rosenbaum, Chief Executive Officer of Guidewire Software, executed 2 separate sales totaling 7,325 shares for $1,831,299.65, reducing his holdings by 3.0% from 245,993 shares to 238,668 shares. The blended average transaction price of $250.01 sits near the current price of $246.79, suggesting the sales occurred close to prevailing market levels. Against his cross-ticker track record showing an average 90-day return of +20.5% after sells with a 12.50% well-timed rate, this insider has historically been poorly timed at this ticker in particular: his prior 5 sales at GWRE show only 1 well-timed outcome at the 90-day mark, with recent sales on 2025-03-18 and 2025-03-17 followed by strong 90-day gains of +33.9% and +36.8%, indicating he sold before substantial rallies. The company trades at a P/E of 601.93 and was unprofitable over its most recent full fiscal year, though revenue grew 8.3% year-over-year and the stock has rallied 27.6% over 90 days—a context in which the CEO's sell appears contrarian to recent momentum.

CEO Michael Rosenbaum sells 6,337 shares at $188.44 avg for $1,194,175.96; holds 262,793 post-sale

Michael Rosenbaum, CEO of Guidewire Software, executed 2 separate sales totaling 6,337 shares for $1,194,175.96 on March 17–18, 2025, at prices of $185.03 and $189.41. This reduces his holdings by 2.4% to 262,793 shares. The sales occurred when the stock was trading near recent highs ($196.26 currently, just 10.1% below the 52-week peak of $218.22), and the company remains unprofitable with net income of $-37,277,000.00 over its most recent full fiscal year despite posting 8.3% annual revenue growth to $289,480,000.00. Rosenbaum's prior 5 sales at GWRE have shown mixed timing outcomes, with only 1 of 5 well-timed at the 90-day mark, suggesting no strong pattern of prescient exits at this holding. The current sale occurs in a context of elevated valuation and persistent unprofitability, but the modest scale (2.4% portfolio reduction) and lack of any prior clear pattern of well-timed selling at this ticker limits the strength of any directional signal from this transaction alone.

CEO Rosenbaum sells 5,932 shares of GWRE at $171.06; stock down 10.1% in 30 days from sale date.

CEO Michael George Rosenbaum sold 5,932 shares on 2024-12-17 at $171.06, reducing his holdings by 2.1% to 281,730 shares total. The stock has declined 10.1% over the 30-day period following the sale, and currently trades at $174.52 (still below the 52-week high of $207.12 by 15.7%). At the GWRE ticker level, Rosenbaum's prior five sales showed mixed timing: three generated positive 90-day returns (poorly-timed sells), while one produced a negative 90-day return (well-timed). His cross-ticker track record shows 5 prior sells with a 20.00% well-timed rate and an average 90-day return of +16.2%, indicating that his sells historically have not preceded sharp declines. The company's P/E of 484.78 and full-year net loss (despite quarterly net income of $9.1M) reflect valuation and profitability concerns that may warrant investor scrutiny of execution trends.

GWRE CEO Rosenbaum sells 23,379 shares at $172.16; stock near 52-week high, up 27.2% in 90 days, company unprofitable.

Michael George Rosenbaum, CEO of Guidewire Software, sold 23,379 shares at $172.16 on 2024-09-17, reducing his holdings from 311,041 to 287,662 shares. The sale occurs near the 52-week high of $173.03 as the stock has appreciated 27.2% over the prior 90 days. At Guidewire specifically, Rosenbaum's four prior open-market sales (2023–2024) produced mixed timing outcomes: two followed by strong 90-day gains (31.0% and 28.4%), one by a modest 9.4%, and one by a slight 2.9% decline, with a 0% "well-timed rate" indicating none preceded material downturns. The company remains unprofitable with net income of $-5,478,000.00 over the latest fiscal year, though revenue of $240,678,000.00 reflects 8.3% annual growth. The sale signal is muted: the CEO's 7.5% reduction in stake at a cyclical peak does not clearly separate conviction from routine liquidity management, particularly given the pattern of prior sales that have typically not preceded downturns.

CEO Michael George sold 5,582 shares of GWRE at $134.54 for $750,988.33 on 2024-06-18

Michael George, Chief Executive Officer of Guidewire Software, sold 5,582 shares at $134.54, reducing his holdings by 2.3% to 239,793 shares. At the time of sale, the stock was trading near its 52-week high ($135.51 current vs $69.00–$136.00 range), and the company was unprofitable with a net loss of $-5,478,000 in its most recent quarter despite revenue growth of 11.4%. Examining his same-ticker history at GWRE, all three prior sales in 2023 resulted in positive 90-day returns (8.0%, 9.4%, and 31.0%), meaning the stock appreciated after each sale—a pattern of poorly-timed exits from a valuation perspective. This transaction follows the established pattern, with the stock subsequently up 19.6% over 90 days post-transaction, suggesting the sale again preceded significant gains.