Khozema Shipchandler

CEO Shipchandler sells 14,458 shares for $3,042,343.09 via 10b5-1 plan at TWLO on 2026-07-06

Khozema Shipchandler, CEO of Twilio, executed 6 separate sales totaling 14,458 shares for $3,042,343.09 across prices ranging from $206.99 to $213.25 per share. This transaction is part of a pre-arranged 10b5-1 trading plan, meaning it is scheduled rather than discretionary, and thus does not reflect a real-time judgment call by the CEO about valuation. The CEO's post-transaction holdings are 207,203 shares, representing a 6.5% reduction from his prior position of 221,661 shares. Notably, across his cross-ticker insider transaction history, Shipchandler's 20 prior sells have averaged a 90-day return of +42.3%, though his same-ticker history at TWLO shows mixed recent outcomes, with his most recent sell on 2026-06-04 followed by a 30-day decline of 11.3%. The scheduled nature of this sale precludes timing-based interpretation.

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 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.

Twilio CEO Khozema Shipchandler sold 12,922 shares for $1,344,998.19 via scheduled 10b5-1 plan

Khozema Shipchandler, Chief Executive Officer of Twilio Inc, executed 2 separate sales totaling 12,922 shares for $1,344,998.19 on 2025-10-03 at a blended average price of $104.09. The transaction was executed under a pre-arranged 10b5-1 trading plan, meaning the sales were scheduled in advance rather than discretionary. Post-transaction holdings of 220,383 shares represent a 5.5% reduction from the 233,305 shares held prior. Since this activity was scheduled under Rule 10b5-1, no inference about timing or conviction can be drawn from the execution date.

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 Khozema sold 7,000 shares ($872.0K) via scheduled 10b5-1 plan on 2025-06-30.

CEO Khozema sold 2 separate tranches totaling 7,000 shares for $872,011.17 at blended average price $124.57 under a pre-arranged 10b5-1 trading plan on 2025-06-30. Since the sales were scheduled under a 10b5-1 plan rather than discretionary, no timing inference or insider conviction signal is applicable. Post-transaction, Khozema retains 260,581 shares, representing a 2.6% reduction in holdings. The sale magnitude and structured nature of execution are routine administrative components of an established trading plan, not indicators of material underlying concern or strategic repositioning.

CEO Khozema sells 14,545 shares at avg $91.61 for $1.3M under 10b5-1 plan; holdings fall 4.9%

Shipchandler Khozema, Chief Executive Officer of Twilio, executed 5 separate sales totaling 14,545 shares for $1,332,426.45 on April 3, 2025, pursuant to a pre-arranged 10b5-1 trading plan. His shareholding decreased from 295,134 shares to 280,589 shares, representing a 4.9% reduction in holdings. Because this activity is part of a scheduled trading plan rather than discretionary trading, it reflects a pre-committed disposition strategy established in advance rather than a response to current market conditions or company-specific developments.

TWLO CEO Khozema Shipchandler sold 10,834 shares for $1,230,544.39 (blended avg $113.58/sh) on 2025-01-06.

Shipchandler executed 2 separate sales totaling 10,834 shares for $1,230,544.39 at prices of $113.31 and $113.82 on 2025-01-06, reducing his holdings by 4.2% to 244,971 shares. The transaction occurred near the 52-week high ($114.96), with stock currently at $111.06 (-3.4% from the high). At the same-ticker level, Shipchandler's prior 4 measurable TWLO sales (2024-07-05 through 2024-10-03) all posted positive 90-day returns (+11.7% to +68.1%), indicating he has not successfully timed downturns in this stock; 0 of 4 were well-timed. His cross-ticker track record shows avg 90d return +21.2% after 13 prior sells, with 33.33% achieving negative 90-day returns (well-timed rate). Against this backdrop, the current sale occurs after a 90-day rally of +58.4% in TWLO, though the company remains unprofitable with most recent net income of $-9.7M against $1.1B revenue.