Sean Michael Walters

CRO Sean Walters sells 11,876 shares at Datadog for $2.7M via 9 separate transactions on 2026-06-11.

Sean Michael Walters, Chief Revenue Officer at Datadog, Inc., executed 9 separate sales totaling 11,876 shares for $2,743,550.97 on 2026-06-11 at prices ranging from $225.18 to $233.91, with a blended average price of $231.02. This transaction is part of a pre-arranged 10b5-1 trading plan and therefore represents a scheduled, non-discretionary activity rather than a discretionary decision. His post-transaction holdings of 258,420 shares represent a -4.4% reduction from pre-transaction holdings of 270,296 shares. At the same ticker, his prior four measurable sales (in March and May 2026) show mixed subsequent price performance: 30-day returns of -15.7%, -17.4%, -16.4%, and +24.2%, with 90-day returns of +81.9%, +78.3%, and +80.4% on the March sales. The current stock price of $233.09 is -16.4% from the 52-week high of $278.70, though it has appreciated +12.1% over the past 30 days and +80.9% over the past 90 days.

CRO Sean Walters sold 13.4K DDOG shares at $267.15 for $3.6M; holds 270.3K post-trade.

Sean Michael Walters, Chief Revenue Officer, sold 13,409 shares of Datadog at $267.15 on 2026-06-02, reducing his position by 4.7%. The sale occurred near the stock's 52-week high of $278.70, with the current price at $250.33. Notably, Walters' five prior sales at Datadog all showed positive 90-day returns (ranging from +32.8% to +100.3%), with 0 of 5 prior sells well-timed (meaning the stock continued to rise after each sale rather than decline). His cross-ticker track record of 20 prior sells shows a 90d well-timed rate of only 15.00%, indicating limited predictive timing ability across his broader trading history. The company reports strong fundamentals with $1.0B in latest quarterly revenue and +27.7% annual growth, though a notably elevated P/E of 807.52 reflects the stock's valuation premium.

Datadog CRO Sean Walters sells 7,657 shares for $1.44M as stock hits 52-week high; selling from a 66-trade open-market sales streak with mixed short-term but persistently poor long-term timing.

Sean Walters, Chief Revenue Officer at Datadog, sold a meaningful block of shares while the stock trades at its 52-week high, representing roughly 2.6% of his holdings. This is the 67th open-market sale Walters has executed in the past three years, underscoring a consistent pattern of selling rather than accumulating equity. His prior exits at this company show conflicting timing results: in the short term, most previous sales were well-timed as the stock declined afterward, but over longer horizons all prior sales proved poorly timed as the stock recovered significantly in each instance. Datadog itself is a profitable, fast-growing company, and selling into its strongest price levels could reflect either a desire to lock in gains or rebalancing after the stock's substantial recent rally. The persistent nature of these sales—combined with their mixed near-term but uniformly poor long-term outcomes—suggests an insider with a pattern of exiting only to watch shares climb further.

CRO Sean Michael Walters sells 22,330 DDOG shares for $2,806,479.21 (avg $125.68); retains 238,384 shares, stock down 37.6% from 52-week high.

Sean Michael Walters, Chief Revenue Officer of Datadog, executed 4 separate sales totaling 22,330 shares for $2,806,479.21 on 2026-03-11 at blended average price of $125.68. His post-transaction holdings of 238,384 shares represent an 8.6% reduction from pre-transaction levels. The timing context is material: the stock is currently at $124.52, down 37.6% from its 52-week high of $199.72, and has declined 14.7% over the past 90 days. His same-ticker trading history at DDOG shows a clear pattern: 3 of his 4 prior measurable sales were well-timed at the 90-day mark, with outcomes ranging from -14.3% to -29.9% post-sale, while the company maintains strong fundamentals (revenue growth of 27.7% year-over-year and $885.7M quarterly revenue). This sale occurs against a backdrop of recent sharp declines and historical discipline in insider execution at this ticker specifically.

CRO Sean Walters sold 32,118 shares (11% of holdings) at $110.54 as DDOG declines 40.8% from 52-week high

Sean Michael Walters, Chief Revenue Officer of Datadog, sold 32,118 shares at $110.54 on 2026-03-02 for $3,550,192.04, reducing his holdings by 11.0% to 260,714 shares. The sale occurred as DDOG trades $118.33 (current), down 40.8% from its 52-week high of $199.72 and down 22.7% over 90 days. At the same-ticker level, Walters' recent prior sells (2025-12-11 and 2025-12-02) show negative 30-day returns of -16.1%, -16.4%, and -14.3% respectively, indicating a pattern of selling into weakness at this stock. While his cross-ticker track record shows 38.89% well-timed sell rate, his DDOG-specific history reveals only 1 of 3 prior measurable 90-day outcomes were well-timed, suggesting his timing acuity at this particular ticker is not representative of his broader performance. The sale's significance is elevated by the magnitude (11% reduction) and the stock's sharp recent decline, though the company's fundamentals remain solid with $885.7M quarterly revenue and 27.7% annual growth.

CRO Sean Walters sells 9,838 shares at $149.84 blended price; stock now -28.9% from 52-week high after -23.2% 30-day slide.

Sean Michael Walters, Chief Revenue Officer of Datadog, Inc., executed 2 separate sales totaling 9,838 shares for $1,474,096.64 on 2025-12-11, representing a 5.4% reduction in his holdings to 171,654 shares post-transaction. The transaction occurred at a blended average price of $149.84, which exceeds the current price of $142.05 by approximately 5.6% in retrospect. DDOG has experienced significant recent weakness: the stock is -28.9% from its 52-week high of $199.72 and has declined -23.2% over the prior 30 days, though it is still +5.5% over the 90-day period. His prior 4 measurable DDOG sales (all executed in September 2025) showed uniformly positive 90-day returns ranging from 7.2% to 18.0%, meaning the stock rose after those sales—a pattern of poorly-timed exits at this ticker. This current sale occurs near recent lows, after a sharp pullback, which structurally differs from his prior September sales timing. The P/E of 258.27 and year-over-year revenue growth of +26.1% suggest the stock trades at an elevated multiple relative to profitability, a context worth monitoring for future price action.

Datadog CRO sells 10,530 shares at $158.60; stock now at $153.00, down 23.4% from 52-week high

Sean Michael Walters, Chief Revenue Officer of Datadog, sold 10,530 shares at $158.60 on 2025-12-02, reducing his position to 181,492 shares (a 5.5% reduction). The sale occurred when the stock was trading $5.60 above the current price of $153.00 and approximately 23.4% below its 52-week high of $199.72, indicating the sale was executed near a recent elevated price level. His cross-ticker track record shows 20 prior open-market sells with a 47.06% well-timed rate and -4.7% average 90-day return, suggesting his sells have historically been poorly timed at the 90-day horizon; at Datadog specifically, his prior measurable same-ticker sell (2025-09-02) was followed by an 18.0% gain at 90 days, further indicating poor timing on this ticker. The company's fundamentals remain strong with $885.7M in quarterly revenue and 26.1% annual revenue growth, but the elevated P/E of 278.18 reflects significant valuation premium that may constrain upside momentum.

Datadog CRO sells 6,821 shares for $952,343.60; holds 194,881 shares post-transaction.

Sean Michael Walters executed 3 separate sales totaling 6,821 shares for $952,343.60 on 2025-09-11, representing a 3.4% reduction in holdings to 194,881 shares. The blended average sale price of $139.62 is above the current price of $136.50, placing the transaction in a context where the stock has declined 19.1% from its 52-week high but risen 6.0% over the past 30 days and 13.3% over 90 days. Across his prior 5 trades at Datadog, Walters' timing has been inconsistent: only 0 of 2 measurable 90-day periods resulted in well-timed sells (stock declining post-sale), including a June 2025 sale that saw the stock rise 17.0% in the following 90 days. His cross-ticker track record shows a 52.94% well-timed rate with an average 90-day return of -4.2% after sales, suggesting moderately accurate but not exceptional sell timing historically. The current sale occurs at an elevated price relative to the stock's recent floor but following strong near-term performance.

Datadog CRO Sean Michael Walters sold 10,622 shares at $133.85 on 2025-09-02; still holds 201,702 shares post-sale.

Sean Michael Walters, Chief Revenue Officer of Datadog, sold 10,622 shares (representing a 5.0% reduction from his 212,324 pre-transaction holdings) for $1,421,721.77 total value. The sale occurred at $133.85, and the stock now trades at $131.78, approximately 21.9% below its 52-week high of $168.65. Across his prior open-market activity on Datadog, Walters has executed 5 trades; his last two sales (2025-07-03 and 2025-06-17) showed divergent outcomes, with the June 17 sale proving poorly timed (+14.5% in 30 days) despite the July 3 sale declining 9.6%. His cross-ticker track record spans 20 prior sells with an average 90-day return of -4.0%, but applied to this ticker's historical context, none of his 3 prior measurable Datadog 90-day sell outcomes were well-timed (3 of 3 posted positive 90-day returns, meaning he sold before subsequent gains). This transaction maintains Walters' substantial residual position at 201,702 shares while the company reports recent quarterly revenue of $826,760,000.00 with 26.1% annual revenue growth, though elevated valuation metrics and modest recent selling activity offer limited timing signal.

DDOG CRO Sean Walters sells 9,469 shares at $150.00 on 2025-07-03; holds 212,324 shares post-sale

Sean Michael Walters, Chief Revenue Officer of Datadog, sold 9,469 shares at $150.00 for $1,420,350.00, reducing his holdings to 212,324 shares. This represents a -4.3% reduction from his pre-transaction holdings of 221,793 shares. The sale occurred at a price $4.06 above the current market price of $145.94, and notably within the 52-week range of $87.00–$168.65, positioning the trade at 13.5% below the 52-week high. Reviewing Walters' same-ticker history at DDOG reveals 5 prior trades, all sales, with a poor timing pattern: his three measurable 90-day outcomes (from March 2025) showed the stock rising +17.1%, +18.0%, and +19.0% after his sales, meaning 0 of 3 prior same-ticker sales were well-timed. His cross-ticker track record across 20 prior sells shows an average 90-day return of -5.1%, with a 61.11% well-timed rate, yet this aggregate metric cannot be assumed to predict DDOG-specific performance. The recent 30-day and 90-day price appreciation (+19.5% and +49.8% respectively) contextualizes this as a sale into sustained strength, consistent with his historical pattern of selling into uptrends at this ticker.