Khozema Shipchandler

CEO Khozema Shipchandler sold 44,158 shares of TWLO at $235.88 ($10.4M) under pre-arranged 10b5-1 plan; retains 235,542 shares post-sale.

CEO Khozema Shipchandler executed a scheduled sale of 44,158 shares at $235.88, totaling $10,416,148.01, under a pre-arranged 10b5-1 trading plan. The current price of $212.54 is -10.9% from the 52-week high of $238.48, and the stock has returned +5.4% over 30 days and +69.8% over 90 days. This represents the CEO's sixth documented trade at TWLO in recent days, following five prior sales on 2026-05-26; his cross-ticker track record across 20 prior open-market sales shows an average 90-day return of +38.5%, while his five prior TWLO-specific trades returned +20.2% to +22.4% over 90 days. The scheduled nature of this sale under a 10b5-1 plan indicates the transaction was pre-determined rather than discretionary. Post-sale, Shipchandler holds 235,542 shares, down from the pre-transaction 279,700 shares, a reduction of -15.8% of his prior holdings.

Khozema Shipchandler (CEO) executes 8 scheduled sales totaling 32,158 shares for $5,971,687.67 under 10b5-1 plan at TWLO

Khozema Shipchandler, Chief Executive Officer of Twilio, completed 8 separate open-market sales on 2026-05-26 totaling 32.2K shares for $6.0M at a blended average price of $185.70. This transaction is part of a pre-arranged 10b5-1 trading plan and therefore reflects a scheduled, non-discretionary execution rather than a timing-driven decision. Post-transaction, Shipchandler retains 235.5K non-derivative shares (a reduction of 12.0% vs pre-transaction holdings), plus 3,260 employee stock options. His prior sales at Twlio over the past two months generated average 30-day returns of +43.0% (across 5 prior sales on 2026-04-06 and 2026-03-31), though the current price of $181.57 sits 10.9% below the 52-week high, indicating meaningful volatility in the intermediate term. As a pre-arranged 10b5-1 sale, this filing does not signal discretionary conviction either toward or away from the stock; it reflects contractual execution according to a preset schedule.

Twilio CEO Khozema Shipchandler sells 15,715 shares across 4 transactions totaling $2.1M at blended average $133.39

CEO Khozema Shipchandler executed 4 separate sales totaling 15,715 shares for $2,096,192.87 on 2026-04-06, reducing his holdings by 6.3% to 235.5K shares. The sales occurred across a narrow pricing band ($131.93–$135.02), near the company's 52-week high of $144.14 and above the current price of $129.61. Across his entire open-market trading history, his 20 prior sells averaged a 90-day return of +7.0% with a 62.50% well-timed rate, but at Twilio specifically, his 5 prior trades show mixed outcomes—his most recent measurable sale on 2026-01-06 saw a 90-day decline of -2.2%. The company's P/E of 93.24 against net income of $37.2M and annual revenue growth of +13.7% reflects a premium valuation that may constrain forward returns.

CEO Khozema Shipchandler sells 12,624 TWLO shares for $1,550,337.25 across 4 transactions at $122.35–$125.06

CEO Shipchandler executed 4 separate sales totaling 12,624 shares for $1,550,337.25 on 2026-03-31 at prices ranging from $122.35 to $125.06, reducing holdings by 4.8% to 251,257 shares. The current price of $130.95 is 6.5% above the blended average sale price of $122.81, suggesting the transaction would have been better executed at today's market level. At the same ticker (TWLO), his prior 5 trades show a mixed timing pattern: the most recent three January sells have already declined 18–19% within 30 days, while an earlier October 2025 sale was followed by strong 90-day gains of +37.7%, indicating inconsistent execution timing at this specific holding. The company trades at a P/E of 94.21 on $1.3B quarterly revenue growth of +13.7%, valuation metrics that may influence insider appetite for diversification.

CEO Khozema Shipchandler sold 13,336 shares at avg $134.28 on 2026-01-06 for $1.8M, reducing holdings by 6.4%.

Khozema Shipchandler, CEO of Twilio, executed 3 separate sales totaling 13,336 shares for $1,790,778.45 on 2026-01-06, with a blended average price of $134.28. The current stock price is $137.43, meaning the CEO sold below current market levels; the stock has appreciated 6.0% over the past 30 days and 28.3% over the past 90 days. Notably, his prior 4 measurable sales at Twilio (dating back to September 2025) all generated positive 90-day returns, ranging from +36.3% to +42.6%, indicating the stock consistently rose after those sales—a pattern of poorly-timed exits at this specific ticker. Against this backdrop of misjudged sales timing, this latest transaction represents a modest reduction (6.4%) of his 193.8K share position, which remains substantial.

CEO Khozema sells 13,266 shares of TWLO at $143.37 for $1,901,947.75; 0 of 5 prior same-ticker sales were well-timed by 90d mark.

Chief Executive Officer Khozema sold 13,266 shares (13.3K shares) at $143.37, reducing holdings by 6.0% to 207,117 shares. The sale price is 5.2% above the current price of $136.24 and within 3.5% of the 52-week high of $148.35. Notably, across his 5 prior sales at TWLO, none proved well-timed at the 90-day mark—all exhibited positive 90-day returns (ranging from +36.3% to +42.6%), indicating the stock rose after each prior sale. His broader cross-ticker track record shows an average 90-day well-timed rate of 35.00% across 20 prior sells, but the TWLO-specific pattern (0 of 5 well-timed) is significantly weaker. The company's P/E of 309.64 is elevated, and full-year profitability remains absent despite recent quarterly earnings of $37.2M, warranting attention to whether this sale reflects execution of a pre-set plan or discretionary conviction.

CEO Khozema Shipchandler sells 12,922 shares at $103.30–$104.37 ($1.3M); stock down 11.5% in 90 days

Khozema Shipchandler, CEO of Twilio, sold 12,922 shares across 2 separate transactions on 2025-10-03 at prices of $103.30 and $104.37, generating $1,344,998.19 total and reducing holdings by 5.5% to 220,383 shares. The sales occurred at the current price's $107.55 level, and TWLO is trading 27.5% below its 52-week high with a 90-day decline of 11.5%. His cross-ticker track record shows a 52.94% well-timed sell rate (avg 90d return +3.6%), but at TWLO specifically, prior measured sales on 2025-07-03 posted 90-day returns of -12.0% and -13.2%, both well-timed declines. The company posted a negative full-year net income, though the latest quarter showed $22,423,000.00 in net income and annual revenue growth of 7.3%; the elevated P/E of 827.31 reflects profitability volatility. The pattern of CEO selling into a stock that has declined significantly over the recent period, combined with Twilio's weak profitability structure, merits investor attention to underlying operational trends.

CEO Khozema Shipchandler sold 13,681 shares across 3 transactions for $1,376,145.51 on 2025-09-30; maintains 233,305 shares post-sale.

Shipchandler executed three separate sales totaling 13,681 shares at a blended average price of $100.59, reducing holdings by 5.5% while retaining substantial position of 233,305 shares. His prior five trades at TWLO all generated negative 90-day returns (ranging from -12.0% to -18.0%), establishing a consistent pattern of well-timed sales at this ticker—all five preceded subsequent stock declines. Against this backdrop, the current stock price of $105.42 sits 28.9% below the 52-week high of $148.35, and has fallen 12.4% over the past 90 days. The company's fundamentals present a conflicting picture: revenue of $1,228,425,000 with recent annual growth of 7.3%, yet the company remains unprofitable on a full-year basis with net income negative, and the P/E ratio of 810.92 reflects minimal earnings. The CEO's continuing sales history at this ticker, combined with ongoing execution despite suppressed valuations, warrants attention to whether cash deployment signals align with internal outlook.

CEO Khozema sold 13,595 shares at blended $117.06 on 2025-07-03 for $1,591,376.29

CEO Khozema executed three separate sales totaling 13,595 shares for $1,591,376.29 at prices ranging from $116.69 to $118.33, reducing holdings by 5.2% to 246,986 shares post-transaction. At his cross-ticker track record, prior sells have not consistently preceded declines: the average 90-day return after his sells was +23.0%, indicating poor timing (stock rose after he sold), with only a 17.65% well-timed rate. His TWLO-specific history shows 0 of 2 measurable prior sells were well-timed, though recent trades from 2025-06-30 lack outcome data. The company's fundamentals show revenue of $1,172,463,000.00 and recent quarterly net income of $20,017,000.00, though full-year results were unprofitable; the current price of $122.12 sits 17.7% below the 52-week high but up 32.8% over 90 days. The sale occurs in a period of relative strength, with no immediate fundamental catalysts apparent.

Twilio CEO sold 20,008 shares for $2.5M at $124.53 on 2025-06-30; stock now $116.51 after declining 2.6% in 30 days.

CEO Khozema Shipchandler executed 3 separate sales totaling 20,008 shares (20.0K shares) for $2,491,593.02 ($2.5M) at a blended average price of $124.53, reducing holdings by 7.1% to 260,581 shares. The current price of $116.51 is 21.5% below the 52-week high of $148.35, but the stock has risen 30.1% over the prior 90 days despite the 2.6% decline in the past 30 days. Across his cross-ticker track record, Shipchandler's 20 prior sells returned an average of 17.8% over 90 days with a well-timed rate of 30.00%, yet his 5 prior sales at Twilio all saw positive 90-day returns, meaning none were well-timed by sell standards. This filing does not carry scheduling flags that would preclude timing analysis. The company posted $1.2B quarterly revenue with 7.3% annual growth, though full-year net income was negative, which contrasts with the recent $20.0M quarterly profit shown here.