Cooper Jeffrey Elliott

CFO Cooper Jeffrey Elliott sold 4,757 shares of GWRE at $158.72; well-timed prior sales suggest pattern of selling before declines.

Cooper Jeffrey Elliott, GWRE's CFO, sold 4,757 shares on 2026-03-13 at $158.72, reducing his holdings from 72,753 to 67,996 shares. His prior trades at GWRE show a consistent pattern: three measurable sales at the 90-day mark (2025-09-18 triple sale) all registered negative 90-day returns of -22.5%, -22.4%, and -22.0%, indicating well-timed exits before declines. More recently, two December 2025 sells showed 30-day declines of -18.5% and -13.5%, suggesting the insider continues to sell into strength. The current stock price of $160.57 is down 38.7% from its 52-week high of $261.88, placing this sale approximately midway through a significant retreat; whether this sale precedes further weakness or occurs after the main decline will become measurable in subsequent 90-day reporting. The CFO's same-ticker history (3 of 3 prior 90-day outcomes well-timed) warrants monitoring of post-transaction price action.

GWRE CFO Elliott sells 4,104 shares for $791,882.56; GWRE trades -24.6% from 52-week high; 5 of 5 prior Elliott sales at GWRE well-timed.

Cooper Jeffrey Elliott, CFO of Guidewire Software (GWRE), executed two separate sales totaling 4,104 (4.1K shares) for $791,882.56 on December 16 and 18, 2025, at prices of $192.08 and $195.00 respectively (blended average $192.95). This reduces his holdings by 5.3%, from 77,073 to 72,969 shares. Notably, all five of Elliott's prior sales at GWRE (executed on 2025-09-18) were well-timed at the 90-day mark, with negative post-sale returns ranging from -1.0% to -22.5%, meaning the stock declined after each sale. Elliott's cross-ticker track record shows a 45.00% well-timed rate across 20 open-market sales, suggesting moderate timing accuracy. The current stock price of $197.46 stands -24.6% below the 52-week high of $261.88 and has fallen 19.3% over the past 90 days, placing the company in a period of sustained weakness relative to recent valuations.

CFO Cooper Jeffrey Elliott sold 7,535 shares at blended average $248.76 for $1.9M at Guidewire Software

Cooper Jeffrey Elliott, CFO of Guidewire Software, executed 5 separate sales totaling 7,535 shares for $1,874,377.21 on 2025-09-18, reducing his holdings by 8.9% from 84,646 to 77,111 shares. The sales occurred at prices ranging from $246.80 to $250.28, with a blended average of $248.76, slightly above the current price of $244.60. Across his cross-ticker track record, his prior sells showed an average 90-day return of +14.2% with a 90-day well-timed rate of 17.65%, indicating his historical sales have predominantly preceded stock appreciation rather than declines. At this specific ticker (GWRE), his prior 4 measurable sales showed mixed outcomes: 2 of 4 were well-timed at the 90-day mark, with his most recent prior sell on 2025-06-18 declining 11.3% over 30 days and 1.5% over 90 days. The company trades at a P/E of 186.72 with strong recent fundamentals including $293.5M quarterly revenue and +22.6% annual revenue growth, though the current price sits 6.6% below its 52-week high of $261.88.

CFO Cooper Jeffrey Elliott sold 14,103 shares of GWRE at $242.87 on 2025-09-16 for $3.4M, reducing holdings by 14.3%

Cooper Jeffrey Elliott, CFO of Guidewire Software, sold 14,103 shares at $242.87 on 2025-09-16 for a total value of $3,425,150.48, reducing his stake from 98,749 shares to 84,646 shares—a 14.3% reduction in holdings. The sale occurred when the stock was trading -5.7% below its 52-week high of $261.88, during a period of +14.8% upward momentum over the prior 30 days. His prior trades at Guidewire show a mixed timing pattern: 2 of 5 prior sales resulted in stock declines over 90 days (well-timed outcomes), while the other 3 were followed by stock appreciation, including two sales in March 2025 followed by +28.5% and +29.7% 90-day gains. The cross-ticker timing record is stronger (17.65% well-timed rate), but same-ticker results suggest this CFO has not consistently sold ahead of declines at Guidewire specifically. The sale represents a substantial reduction in equity ownership while the company reports strong fundamentals: $293.5M quarterly revenue, $46.0M net income, +22.6% annual revenue growth, and a $20.9B market cap.

CFO Jeffrey Elliott sells 4,411 shares ($1.1M) at blended $249.12; holds 65.0K shares post-sale

Cooper Jeffrey Elliott (Chief Financial Officer) executed 3 separate sales totaling 4,411 shares for $1,098,879.46 ($1.1M) on June 17–18, 2025, reducing his holdings from 69.4K to 65.0K shares (a 6.4% reduction). The sales occurred at a blended average price of $249.12, near the 52-week high of $257.37, at a time when the stock has risen 14.6% over 30 days and 27.6% over 90 days. His prior 5 trades at GWRE (all sales in March 2025) showed mixed post-transaction timing: none achieved a well-timed 90-day outcome (all posted gains of +27.3% to +33.9% after the sale, indicating the stock continued rising rather than falling), while his cross-ticker track record shows a 90-day well-timed rate of 7.14%, modestly above zero. The company's fundamentals are noteworthy: it is unprofitable on a full-year basis despite $293.5M quarterly revenue and $46.0M net income in the latest quarter, with an elevated P/E of 601.93, reflecting recent profitability swings or very thin margins. Against this context, the sale represents a material reduction in his equity stake while the stock is near its 52-week peak.

CFO Elliott sells 4,063 shares at $189.41–$194.98; holds 69,431 shares post-transaction

Cooper Jeffrey Elliott, CFO of Guidewire Software, executed 5 separate sales totaling 4,063 shares for $777,554.58 over two trading days (March 18–19), reducing his holdings by 5.5% from 73,494 to 69,431 shares. The blended average price of $191.37 falls within the 52-week range of $107.64–$218.22, and occurs as the stock is currently -11.4% from its 52-week high and -10.2% over the past 30 days. Elliott's cross-ticker track record shows a 90-day well-timed rate of 11.11% across 9 prior sells, but his same-ticker history at GWRE is notably weaker: all 5 prior sales were poorly timed at the 90-day horizon (positive returns after each sale, 0 of 5 well-timed). The company remains unprofitable with a net income of -$37.3M on quarterly revenue of $289.5M, though annual revenue growth stands at +8.3%. The modest position reduction in the context of recent stock weakness and Elliott's poor historical timing on GWRE trades warrants monitoring but does not signal material concern.

CFO Elliott sells 3,897 shares at blended $171.98; holds 73.8K shares post-sale. GWRE -16.9% from 52-week high.

Cooper Jeffrey Elliott, CFO of Guidewire Software, executed 2 separate sales totaling 3,897 shares for $670,221.37 on December 17-19, 2024, reducing his holdings by 5.0% to 73,842 shares. The stock is currently trading 16.9% below its 52-week high of $207.12 and has declined 12.4% over the past 30 days, creating a depressed price backdrop for the sale. Notably, Elliott's prior 5 same-ticker sales at GWRE (September-June 2024) showed mostly positive 30-day returns averaging around 8.7%, but only 1 of 5 (20%) generated negative 90-day returns that would indicate well-timed selling before a subsequent decline. His cross-ticker track record across 7 prior sells shows a 14.29% well-timed rate, which is weak. The company's fundamentals present a concerning picture: despite $262.9M quarterly revenue and 8.3% annual growth, the business reported only $9.1M net income last quarter and was unprofitable over the full fiscal year, paired with an extremely elevated P/E of 477.94, suggesting the market is pricing in significant future earnings improvement that may not materialize.

CFO Elliott sells 15,290 GWRE shares for $2.6M at $172.34 avg; stock near 52-week high, Elliott retains 78.4K shares

Jeffrey Elliott, CFO of Guidewire Software, executed 4 separate sales totaling 15,290 shares for $2,635,020.17 at a blended average price of $172.34 on September 17–19, 2024. The current price of $174.65 is at the 52-week high, and the stock has rallied +18.9% over 30 days and +27.2% over 90 days. At GWRE specifically, Elliott's prior 3 sales (June 2024 and September 2023) were followed by positive 90-day returns (+28.5%, +28.4%, and +12.8%), indicating poor timing on those occasions. The company remains unprofitable on a full-year basis (net income $-5.5M) with a P/E of 151.87, raising questions about valuation sustainability. Elliott's post-transaction holdings of 78.4K shares represent a 16.3% reduction, yet he retains substantial equity exposure.

CFO Jeffrey Elliott sells 4,782 shares of GWRE for $642,762.64 across two trades; stock near 52-week high at $137.30

Jeffrey Elliott, Chief Financial Officer of Guidewire Software, executed two separate sales totaling 4,782 shares for $642,762.64 on June 18–20, 2024, at an average price of $134.41, reducing his holdings by 7.2% to 61,596 shares. The sales occurred as GWRE trades at $137.30, near its 52-week high of $137.30, having appreciated 11.6% over the prior 30 days and 20.9% over 90 days. Notably, Elliott's prior sale at this ticker on 2023-09-19 was poorly timed—the stock rose 12.8% in the 90 days following that sale, suggesting he sold before a significant gain. The company reported revenue of $240,678,000.00 in its latest quarter with negative net income of $-5,478,000.00, indicating ongoing unprofitability despite 11.4% year-over-year revenue growth. These sales warrant attention as they occur at elevated valuation levels and follow a history of poorly timed insider exits at this security.