TWLO TWILIO INC Insider Trading

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.

CFO Viggiano sold 8,528 TWLO shares at $205.43 via 10b5-1 plan; stock down 7.5% in 30 days.

Aidan Viggiano, CFO of Twilio, executed a scheduled sale of 8,528 shares at $205.43 on 2026-07-02 under a pre-arranged 10b5-1 trading plan, reducing his holdings to 109,724 shares post-transaction. The sale is a routine equity liquidation through a non-discretionary plan structure. At current price of $209.08, the stock stands -7.5% on a 30-day basis and -12.3% from its 52-week high of $238.48, while his prior sales at TWLO have averaged significant positive returns over 90 days (ranging from +59.0% to +64.8% across five prior transactions). Given that this transaction is scheduled rather than discretionary, it carries no timing signal about insider conviction relative to near-term price movements.

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.

Director Andrew Stafman sold 1,000,000 shares of TWLO for $184.1M on 2026-05-27, reducing stake by 61.7%.

Andrew Stafman sold 1,000,000 shares at $184.14, reducing his holdings from 1,620,000 shares to 620,000 shares—a 61.7% reduction in his position. The sale occurred when the stock was trading 10.9% below its 52-week high of $203.71, despite strong recent momentum (30-day return +27.3%, 90-day return +51.8%). Notably, Stafman's two prior sales at TWLO were both well-timed at the 90-day mark, with both resulting in negative subsequent returns, suggesting a pattern of selling ahead of declines. The current sale coincides with a valuation environment marked by an elevated P/E of 267.01 relative to the company's fundamentals, which grew revenues 13.7% year-over-year to $1.4B and generated $90.1M in net income. This substantial director-level sell-off, combined with his historical success timing exits at this ticker, warrants investor attention to near-term price action and any forward guidance changes.

Director Stafman sells 675,000 shares worth $130.6M, his second open-market sale in 36 months.

Stafman Andrew, a director at Twilio, sold a substantial block of shares representing roughly 29% of his holdings. This is his second open-market sale in the 36-month period and occurs while the stock trades just below its 52-week high—a notable timing choice, as most insider selling happens after significant rallies or when insiders view valuations as elevated. His prior sale, conducted roughly five months earlier, was poorly timed in the short term as the stock gained afterward, but well-timed over a longer horizon as it ultimately declined. The current sale happens in a company that remains profitable with strong revenue growth, though it trades at a stretched valuation multiple. Without additional context about Stafman's remaining holdings or his historical trading pattern beyond these two sales, the significance lies in the sheer dollar magnitude and the repeat seller pattern rather than in any clear signal about his conviction in the stock's direction.

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.

CFO Viggiano sells 9,389 shares of TWLO at $127.51 avg for $1.2M on April 2, 2026

Aidan Viggiano, Chief Financial Officer of Twilio, executed two separate sales totaling 9,389 shares for $1,197,215.82 at a blended average price of $127.51 on April 2, 2026, reducing his holdings by 6.7%. The current price of $131.53 is 8.8% below the 52-week high, and his most recent same-ticker sell one day prior (March 31) has no measurable outcome yet. Across his broader open-market history, his 20 prior sells showed a 37.50% well-timed rate over 90 days with an average 90-day return of +14.6%, indicating his historical sales have often occurred before stock declines; however, his single measurable prior sale at this ticker (January 5, 2026) posted a -3.7% 90-day return, showing mixed timing at this specific company. The sales follow a pattern of multiple dispositions within 48 hours and occur while Twilio trades near recent highs, warranting observation of upcoming quarter results and forward guidance.

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.

CFO Viggiano sells 7,213 TWLO shares at $135.97 for $980.8K; stock up 9.8% (30d), 25.4% (90d) post-trade.

Viggiano sold 7,213 shares on 2026-01-05 at $135.97, representing a 6.0% reduction from his 119.4K pre-transaction holdings. The stock has appreciated significantly since the sale: 9.8% over 30 days and 25.4% over 90 days, indicating poorly-timed execution relative to subsequent price action. Across Viggiano's five prior TWLO trades, none achieved negative 90-day returns (the hallmark of well-timed sells); in fact, his prior four measurable trades showed gains of +24.3%, +40.9%, +40.0%, and +42.7% at the 90-day mark, all indicating he sold before rallies. His cross-ticker track record shows a 36.84% well-timed rate (0 of 4 prior TWLO sells were well-timed), and the company remains fundamentally challenged with full-year net income negative, a P/E of 324.77, and annual revenue growth of only 7.3%, despite the recent stock momentum.