Khozema Shipchandler sold $6.0M of TWLO
Chief Executive Officer at TWILIO INC. 32,158 shares at an average of $185.70, traded May 26, 2026, filed May 28, 2026.
Score components
- +25RoleCEO
- +25Trade size$6.0M at market
- +5Share of holdings soldSold 12% of holdings
- +15Cluster4 insiders selling within 14 days
- -15Exercise and sellShares came from an option exercise in the same filing
- -2010b5-1 planPre-scheduled under a 10b5-1 plan
What happened after comparable sells
Same side and tier, against the S&P 500, at 1, 3 and 6 months. Shown to Pro users; the whole table is on the backtest page.
Price around the trade, and since
From a quarter before the trade to today. The arrow is the trade, the circle the day the filing reached EDGAR, which is the first day anyone outside could act; the dotted line is the S&P 500 rebased to that day's close.
Daily candles, adjusted for splits and dividends. Green arrows are insider buys, red are sells, sized by value; the dashed line is the close on the filing day, the dotted line SPY rebased to it.Charts by TradingView Lightweight Charts™
Rows in this filing
Every transaction in Form 4 0001737610-26-000010, as filed. Open on EDGAR
| Date | Transaction | Shares | Price | Value | Holdings after | Filed |
|---|---|---|---|---|---|---|
| May 26, 2026 | MOption exercise Class A Common Stock10b5-1 | +32,158 | $76.63 | $2.5M | 267,700 | May 28, 2026 |
| May 26, 2026 | SOpen-market sale Class A Common Stock10b5-1 | -927 | $180.70 | $168k | 266,773 | May 28, 2026 |
| May 26, 2026 | SOpen-market sale Class A Common Stock10b5-1 | -2,084 | $181.96 | $379k | 264,689 | May 28, 2026 |
| May 26, 2026 | SOpen-market sale Class A Common Stock10b5-1 | -2,677 | $182.75 | $489k | 262,012 | May 28, 2026 |
| May 26, 2026 | SOpen-market sale Class A Common Stock10b5-1 | -3,986 | $184.55 | $736k | 258,026 | May 28, 2026 |
| May 26, 2026 | SOpen-market sale Class A Common Stock10b5-1 | -4,524 | $185.15 | $838k | 253,502 | May 28, 2026 |
| May 26, 2026 | SOpen-market sale Class A Common Stock10b5-1 | -4,719 | $186.55 | $880k | 248,783 | May 28, 2026 |
| May 26, 2026 | SOpen-market sale Class A Common Stock10b5-1 | -8,772 | $187.19 | $1.6M | 240,011 | May 28, 2026 |
| May 26, 2026 | SOpen-market sale Class A Common Stock10b5-1 | -4,469 | $188.00 | $840k | 235,542 | May 28, 2026 |
| May 26, 2026 | MOption exercise Employee Stock Option (right to buy)derivative10b5-1 | -32,158 | $0.00 | $0 | 3,260 | May 28, 2026 |
Related signals
Other insiders at TWILIO INC and this insider’s other filings.
| Score | Company | Insider | Value | Holdings | Filed |
|---|---|---|---|---|---|
| 38Weak | TWILIO INC | Khozema Shipchandler Chief Executive Officer | $4.2M 14,442 shares | -7% | |
| 58Moderate | TWILIO INC | Khozema Shipchandler Chief Executive Officer | $4.1M 13,898 shares | -7% | |
| 55Moderate | TWILIO INC | Aidan Viggiano Chief Financial Officer | $2.7M 9,084 shares | -8% | |
| 52Moderate | TWILIO INC | Aidan Viggiano Chief Financial Officer | $327k 1,394 shares | -1% | |
| 75Notable | TWILIO INC | Andrew Stafman director | $124M 500,000 shares | -81% | |
| 38Weak | TWILIO INC | Erika Rottenberg director | $881k 3,500 shares | -11% | |
| 38Weak | TWILIO INC | Khozema Shipchandler Chief Executive Officer | $3.0M 14,458 shares | -7% | |
| 35Weak | TWILIO INC | Aidan Viggiano Chief Financial Officer | $1.8M 8,528 shares | -7% | |
| 58Moderate | TWILIO INC | Khozema Shipchandler Chief Executive Officer | $2.8M 13,881 shares | -6% | |
| 55Moderate | TWILIO INC | Aidan Viggiano Chief Financial Officer | $1.8M 9,093 shares | -7% |
Not investment advice. Scores and forward returns are decision support built from public SEC filings and past prices; they describe what happened after comparable filings, not what will happen after this one. Do your own research and size your risk.