Denis Oleary

Director Denis Oleary sold 19,250 shares at avg $685.58 for $13.2M on 2026-06-05, reducing holdings to 7,417 shares.

Denis Oleary, a director at CrowdStrike, executed 15 separate sales totaling 19,250 shares for $13,197,414.22 on a single day, with transaction prices ranging from $684.18 to $688.40. This represents a substantial reduction from pre-transaction holdings of 26,667 shares to 7,417 shares post-transaction. His prior trades at CRWD show a 5 of 5 well-timed pattern at the 90-day mark, with his December 2025 sales followed by -12.0% to -12.2% 90-day declines, though the current price of $644.93 is currently -17.9% from the 52-week high of $785.66. The company remains unprofitable with net income of -$33,997,000.00 for the latest quarter, despite annual revenue growth of +21.7%.

Director O'Leary sells 7,750 shares at $515.44 avg for $4.0M, reducing stake by 36.6%; unprofitable CRWD near 52-week highs.

Denis O'Leary, a director at CrowdStrike, executed 4 separate sales on 2025-12-05 totaling 7,750 shares for $3,994,628.64 at a blended average price of $515.44, reducing his holdings from 21.2K shares to 13.4K shares (a 36.6% reduction). The sales occurred near the company's 52-week high of $557.53, with the stock currently at $515.19 and down 7.6% from that peak. O'Leary's same-ticker history at CRWD shows a perfect 5-of-5 pattern of well-timed sells at the 90-day mark, with all prior CRWD sales showing negative 90-day returns (stock declined after). The company remains unprofitable (net income of -$34.0M in the latest quarter), despite 29.4% annual revenue growth and a $129.9B market cap, which adds context to insider sales at elevated valuation levels. The magnitude of the stake reduction (7.8K shares), combined with the historical timing pattern at this ticker and proximity to 52-week highs, represents a material signal warrant observation by shareholders.

O'Leary sold 15,680 shares at blended avg $468.93, reducing CRWD stake by 44.5% to 19.6K shares remaining.

Director Denis O'Leary executed 8 separate sales totaling 15,680 shares for $7,352,769.08 on June 9, 2025, at prices ranging from $468.59 to $469.39. This represents a substantial reduction in his holding from 35.3K to 19.6K shares—a 44.5% decrease. While the stock is up 13.9% over the past 30 days and 34.9% over 90 days, his prior CRWD trades (5 prior trades at this ticker) show 1 of 5 were well-timed at the 90-day mark, with most resulting in gains for the stock after the sale. His cross-ticker track record shows 6 prior sells with a 33.33% well-timed rate and average 90-day returns of -6.8%, indicating his selling has occasionally preceded price declines but not consistently. The company remains unprofitable (full-year net income of $-110.2M), though revenue grew 29.4% year-over-year, so the sale occurs in a context of strong growth but ongoing losses.

Director Denis O'Leary sold 17,530 shares of CRWD for $6,359,008.20 at blended avg $362.75/share on 2024-12-04

Director Denis O'Leary executed 4 separate sales on 2024-12-04, totaling 17,530 shares for $6,359,008.20 at prices ranging from $362.74 to $362.76, reducing his holdings by 45.0% from 38,947 to 21,417 shares. The transaction occurred while the stock trades at $365.65, near the upper end of its 52-week range ($217.89–$392.15) and riding strong recent momentum (+14.3% in 30 days, +48.4% in 90 days). O'Leary's prior sales at CRWD (both on 2024-06-10) each posted -1.8% and -35.4% 90-day returns respectively—a 2 of 2 well-timed pattern at the 90-day mark across his same-ticker history. However, this filing reflects a conversion of derivative securities (Form 4 Table II), so the reported 21,417 shares post-transaction does not represent his total position; investors should monitor derivative holdings separately for the complete picture of his stake. The scale of this reduction—nearly half his common holdings in a single day—during peak valuation deserves attention given the historical timing pattern, though the derivative component limits confidence in assessing total conviction.

Director OLEARY DENIS sold 5,300 shares at $381.45 in 2 transactions for $2,021,685.00 on 2024-06-10

OLEARY DENIS, a director at CrowdStrike, executed 2 separate sales totaling 5,300 shares for $2,021,685.00 on 2024-06-10 at $381.45 per share, reducing his holdings by 17.0% to 25,817 shares post-transaction. The stock is trading at $382.14 currently, near its 52-week high of $390.43, and has appreciated 16.7% over 90 days and 9.4% over 30 days, reflecting strong recent momentum. With the company posting annual revenue growth of 36.3% and $921.0M in latest-quarter revenue, the timing of this director-level sale warrants investor attention regarding insider conviction at current valuation levels.