Insider · CIK 0001737610
Khozema Shipchandler
Files at TWLO (TWILIO INC), LIFE (Ethos Technologies Inc.). First filing Jan 4, 2024, latest Oct 7, 2026.
In brief
Khozema Shipchandler files SEC Form 4 as CEO, director and president at TWLO (TWILIO INC), and also at LIFE (Ethos Technologies Inc.). Since Jan 4, 2024, Khozema Shipchandler has reported 0 open-market buys worth $0 and 17 open-market sells worth $48M, the latest filed on Oct 7, 2026.
A track record needs three past buys with six months of prices behind them; Khozema Shipchandler has 0, so none is measured yet.
The newest scored trade: sold $4.2M of TWLO on Oct 5, 2026, filed Oct 7, 2026, scored 38 (weak), under a 10b5-1 plan. In the last 12 months: 0 buys worth $0 and 10 sells worth $38M.
Where the trades landed
Last year at the company this insider has traded most, with each buy and sell on the bar it happened.
TWLO: TWILIO INC
Daily candles, adjusted for splits and dividends. Green arrows are insider buys, red are sells, sized by value. Click a marked bar to open the signal.Charts by TradingView Lightweight Charts™
Signals
This insider’s open-market buys and sells, scored.
| Score | Company | Value | Holdings | Price context | Filed |
|---|---|---|---|---|---|
| 38Weak | TWILIO INC | $4.2M 14,442 shares | -7% | +183% from low-0% from high | |
| 58Moderate | TWILIO INC | $4.1M 13,898 shares | -7% | +192% from low-2% from high | |
| 38Weak | TWILIO INC | $3.0M 14,458 shares | -7% | +126% from low-12% from high | |
| 58Moderate | TWILIO INC | $2.8M 13,881 shares | -6% | +123% from low-13% from high | |
| 35Weak | TWILIO INC | $10M 44,158 shares | -16% | +156% from low0% from high | |
| 35Weak | TWILIO INC | $6.0M 32,158 shares | -12% | +105% from low-6% from high | |
| 38Weak | TWILIO INC | $2.1M 15,715 shares | -6% | +62% from low-9% from high | |
| 58Moderate | TWILIO INC | $1.6M 12,624 shares | -5% | +55% from low-13% from high | |
| 38Weak | TWILIO INC | $1.8M 13,336 shares | -6% | +71% from low-6% from high | |
| 58Moderate | TWILIO INC | $1.9M 13,266 shares | -6% | +75% from low-4% from high | |
| 38Weak | TWILIO INC | $1.3M 12,922 shares | -6% | +55% from low-31% from high | |
| 58Moderate | TWILIO INC | $1.4M 13,681 shares | -6% | +57% from low-33% from high | |
| 38Weak | TWILIO INC | $1.6M 13,595 shares | -5% | +104% from low-19% from high | |
| 38Weak | TWILIO INC | $2.5M 20,008 shares | -7% | +111% from low-16% from high | |
| 38Weak | TWILIO INC | $1.3M 14,545 shares | -5% | +52% from low-40% from high | |
| 58Moderate | TWILIO INC | $1.2M 12,056 shares | -4% | +66% from low-34% from high | |
| 57Moderate | TWILIO INC | $759k 10,520 shares | -5% | +55% from low-9% from high |
Planned sales
Form 144 notices this insider filed before selling restricted or control stock, newest first.
| Filed | Company | Shares | Value | Sale date | Past 3 months |
|---|---|---|---|---|---|
| Oct 5, 2026 | TWLO TWILIO INC | 14,442 0.01% of outstanding | $4.2M | Oct 5, 2026 | $7.1M |
| Sep 30, 2026 | TWLO TWILIO INC | 13,898 0.01% of outstanding | $4.1M | Sep 30, 2026 | $5.8M |
| Jul 6, 2026 | TWLO TWILIO INC | 14,458 0.01% of outstanding | $3.0M | Jul 6, 2026 | $21M |
| Jun 30, 2026 | TWLO TWILIO INC | 13,881 0.01% of outstanding | $2.8M | Jun 30, 2026 | $20M |
| Jun 4, 2026 | TWLO TWILIO INC | 44,158 0.03% of outstanding | $10M | Jun 4, 2026 | $9.6M |
| May 26, 2026 | TWLO TWILIO INC | 32,158 0.02% of outstanding | $6.0M | May 26, 2026 | $3.6M |
| Apr 6, 2026 | TWLO TWILIO INC | 15,715 0.01% of outstanding | $2.1M | Apr 6, 2026 | $3.3M |
| Mar 31, 2026 | TWLO TWILIO INC | 12,624 0.01% of outstanding | $1.6M | Mar 31, 2026 | $3.7M |
| Jan 6, 2026 | TWLO TWILIO INC | 13,336 0.01% of outstanding | $1.8M | Jan 6, 2026 | $1.9M |
| Dec 31, 2025 | TWLO TWILIO INC | 13,266 0.01% of outstanding | $1.9M | Dec 31, 2025 | $1.3M |
| Oct 3, 2025 | TWLO TWILIO INC | 12,922 0.01% of outstanding | $1.3M | Oct 3, 2025 | $3.0M |
| Sep 30, 2025 | TWLO TWILIO INC | 13,681 0.01% of outstanding | $1.4M | Sep 30, 2025 | $4.1M |
| Jul 3, 2025 | TWLO TWILIO INC | 13,595 0.01% of outstanding | $1.6M | Jul 3, 2025 | $3.8M |
| Jun 30, 2025 | TWLO TWILIO INC | 13,008 0.01% of outstanding | $1.6M | Jun 30, 2025 | $2.5M |
| Jun 30, 2025 | TWLO TWILIO INC | 7,000 0.00% of outstanding | $872k | Jun 30, 2025 | $2.5M |
| Apr 3, 2025 | TWLO TWILIO INC | 14,545 0.01% of outstanding | $1.3M | Apr 3, 2025 | $2.4M |
| Mar 31, 2025 | TWLO TWILIO INC | 12,056 0.01% of outstanding | $1.2M | Mar 31, 2025 | $2.4M |
| Jan 6, 2025 | TWLO TWILIO INC | 10,834 0.01% of outstanding | $1.2M | Jan 6, 2025 | $1.2M |
| Dec 31, 2024 | TWLO TWILIO INC | 11,285 0.01% of outstanding | $1.2M | Dec 31, 2024 | $731k |
| Jan 2, 2024 | TWLO TWILIO INC | 10,520 0.01% of outstanding | $759k | Jan 2, 2024 | $586k |
Transactions
The newest 50 of 75 rows this insider has filed.
| Date | Company | Transaction | Shares | Price | Value | Holdings after | Filed |
|---|---|---|---|---|---|---|---|
| Oct 5, 2026 | TWLO TWILIO INC | SOpen-market sale Class A Common Stock10b5-1 | -1,934 | $288.02 | $557k | 191,371 | 7 d ago |
| Oct 5, 2026 | TWLO TWILIO INC | SOpen-market sale Class A Common Stock10b5-1 | -1,900 | $289.13 | $549k | 189,471 | 7 d ago |
| Oct 5, 2026 | TWLO TWILIO INC | SOpen-market sale Class A Common Stock10b5-1 | -5,156 | $290.24 | $1.5M | 184,315 | 7 d ago |
| Oct 5, 2026 | TWLO TWILIO INC | SOpen-market sale Class A Common Stock10b5-1 | -501 | $291.47 | $146k | 183,814 | 7 d ago |
| Oct 5, 2026 | TWLO TWILIO INC | SOpen-market sale Class A Common Stock10b5-1 | -800 | $292.33 | $234k | 183,014 | 7 d ago |
| Oct 5, 2026 | TWLO TWILIO INC | SOpen-market sale Class A Common Stock10b5-1 | -1,600 | $293.14 | $469k | 181,414 | 7 d ago |
| Oct 5, 2026 | TWLO TWILIO INC | SOpen-market sale Class A Common Stock10b5-1 | -2,551 | $294.53 | $751k | 178,863 | 7 d ago |
| Sep 30, 2026 | TWLO TWILIO INC | SOpen-market sale Class A Common Stock | -260 | $289.98 | $75k | 206,943 | 12 d ago |
| Sep 30, 2026 | TWLO TWILIO INC | SOpen-market sale Class A Common Stock | -1,060 | $291.15 | $309k | 205,883 | 12 d ago |
| Sep 30, 2026 | TWLO TWILIO INC | SOpen-market sale Class A Common Stock | -1,450 | $292.10 | $424k | 204,433 | 12 d ago |
| Sep 30, 2026 | TWLO TWILIO INC | SOpen-market sale Class A Common Stock | -2,330 | $293.44 | $684k | 202,103 | 12 d ago |
| Sep 30, 2026 | TWLO TWILIO INC | SOpen-market sale Class A Common Stock | -5,168 | $294.55 | $1.5M | 196,935 | 12 d ago |
| Sep 30, 2026 | TWLO TWILIO INC | SOpen-market sale Class A Common Stock | -2,670 | $295.56 | $789k | 194,265 | 12 d ago |
| Sep 30, 2026 | TWLO TWILIO INC | SOpen-market sale Class A Common Stock | -960 | $296.29 | $284k | 193,305 | 12 d ago |
| Aug 8, 2026 | LIFE Ethos Technologies Inc. | AGrant or award Class A Common Stock | +7,433 | $0.00 | $0 | 27,312 | Aug 11, 2026 |
| Jul 6, 2026 | TWLO TWILIO INC | SOpen-market sale Class A Common Stock10b5-1 | -2,773 | $206.99 | $574k | 218,888 | Jul 8, 2026 |
| Jul 6, 2026 | TWLO TWILIO INC | SOpen-market sale Class A Common Stock10b5-1 | -1,000 | $208.48 | $208k | 217,888 | Jul 8, 2026 |
| Jul 6, 2026 | TWLO TWILIO INC | SOpen-market sale Class A Common Stock10b5-1 | -2,300 | $210.08 | $483k | 215,588 | Jul 8, 2026 |
| Jul 6, 2026 | TWLO TWILIO INC | SOpen-market sale Class A Common Stock10b5-1 | -4,434 | $211.26 | $937k | 211,154 | Jul 8, 2026 |
| Jul 6, 2026 | TWLO TWILIO INC | SOpen-market sale Class A Common Stock10b5-1 | -2,891 | $212.36 | $614k | 208,263 | Jul 8, 2026 |
| Jul 6, 2026 | TWLO TWILIO INC | SOpen-market sale Class A Common Stock10b5-1 | -1,060 | $213.25 | $226k | 207,203 | Jul 8, 2026 |
| Jun 30, 2026 | TWLO TWILIO INC | SOpen-market sale Class A Common Stock | -1,950 | $199.24 | $389k | 233,592 | Jul 2, 2026 |
| Jun 30, 2026 | TWLO TWILIO INC | SOpen-market sale Class A Common Stock | -3,231 | $200.20 | $647k | 230,361 | Jul 2, 2026 |
| Jun 30, 2026 | TWLO TWILIO INC | SOpen-market sale Class A Common Stock | -4,286 | $201.26 | $863k | 226,075 | Jul 2, 2026 |
| Jun 30, 2026 | TWLO TWILIO INC | SOpen-market sale Class A Common Stock | -1,560 | $202.49 | $316k | 224,515 | Jul 2, 2026 |
| Jun 30, 2026 | TWLO TWILIO INC | SOpen-market sale Class A Common Stock | -2,780 | $203.15 | $565k | 221,735 | Jul 2, 2026 |
| Jun 30, 2026 | TWLO TWILIO INC | SOpen-market sale Class A Common Stock | -74 | $203.89 | $15k | 221,661 | Jul 2, 2026 |
| Jun 4, 2026 | TWLO TWILIO INC | MOption exercise Class A Common Stock10b5-1 | +44,158 | $117.94 | $5.2M | 279,700 | Jun 8, 2026 |
| Jun 4, 2026 | TWLO TWILIO INC | SOpen-market sale Class A Common Stock10b5-1 | -44,158 | $235.88 | $10M | 235,542 | Jun 8, 2026 |
| Jun 4, 2026 | TWLO TWILIO INC | MOption exercise Employee Stock Option (right to buy)derivative10b5-1 | -44,158 | $0.00 | $0 | 0 | Jun 8, 2026 |
| May 26, 2026 | TWLO TWILIO INC | MOption exercise Class A Common Stock10b5-1 | +32,158 | $76.63 | $2.5M | 267,700 | May 28, 2026 |
| May 26, 2026 | TWLO TWILIO INC | SOpen-market sale Class A Common Stock10b5-1 | -927 | $180.70 | $168k | 266,773 | May 28, 2026 |
| May 26, 2026 | TWLO TWILIO INC | SOpen-market sale Class A Common Stock10b5-1 | -2,084 | $181.96 | $379k | 264,689 | May 28, 2026 |
| May 26, 2026 | TWLO TWILIO INC | SOpen-market sale Class A Common Stock10b5-1 | -2,677 | $182.75 | $489k | 262,012 | May 28, 2026 |
| May 26, 2026 | TWLO TWILIO INC | SOpen-market sale Class A Common Stock10b5-1 | -3,986 | $184.55 | $736k | 258,026 | May 28, 2026 |
| May 26, 2026 | TWLO TWILIO INC | SOpen-market sale Class A Common Stock10b5-1 | -4,524 | $185.15 | $838k | 253,502 | May 28, 2026 |
| May 26, 2026 | TWLO TWILIO INC | SOpen-market sale Class A Common Stock10b5-1 | -4,719 | $186.55 | $880k | 248,783 | May 28, 2026 |
| May 26, 2026 | TWLO TWILIO INC | SOpen-market sale Class A Common Stock10b5-1 | -8,772 | $187.19 | $1.6M | 240,011 | May 28, 2026 |
| May 26, 2026 | TWLO TWILIO INC | SOpen-market sale Class A Common Stock10b5-1 | -4,469 | $188.00 | $840k | 235,542 | May 28, 2026 |
| May 26, 2026 | TWLO TWILIO INC | MOption exercise Employee Stock Option (right to buy)derivative10b5-1 | -32,158 | $0.00 | $0 | 3,260 | May 28, 2026 |
| Apr 6, 2026 | TWLO TWILIO INC | SOpen-market sale Class A Common Stock10b5-1 | -2,800 | $131.93 | $369k | 248,457 | Apr 8, 2026 |
| Apr 6, 2026 | TWLO TWILIO INC | SOpen-market sale Class A Common Stock10b5-1 | -5,315 | $133.05 | $707k | 243,142 | Apr 8, 2026 |
| Apr 6, 2026 | TWLO TWILIO INC | SOpen-market sale Class A Common Stock10b5-1 | -5,500 | $133.83 | $736k | 237,642 | Apr 8, 2026 |
| Apr 6, 2026 | TWLO TWILIO INC | SOpen-market sale Class A Common Stock10b5-1 | -2,100 | $135.02 | $284k | 235,542 | Apr 8, 2026 |
| Mar 31, 2026 | TWLO TWILIO INC | SOpen-market sale Class A Common Stock | -5,893 | $122.35 | $721k | 257,988 | Apr 2, 2026 |
| Mar 31, 2026 | TWLO TWILIO INC | SOpen-market sale Class A Common Stock | -4,781 | $122.90 | $588k | 253,207 | Apr 2, 2026 |
| Mar 31, 2026 | TWLO TWILIO INC | SOpen-market sale Class A Common Stock | -1,850 | $123.92 | $229k | 251,357 | Apr 2, 2026 |
| Mar 31, 2026 | TWLO TWILIO INC | SOpen-market sale Class A Common Stock | -100 | $125.06 | $13k | 251,257 | Apr 2, 2026 |
| Feb 21, 2026 | TWLO TWILIO INC | AGrant or award Class A Common Stock | +70,100 | $0.00 | $0 | 263,881 | Feb 24, 2026 |
| Jan 6, 2026 | TWLO TWILIO INC | SOpen-market sale Class A Common Stock10b5-1 | -2,181 | $133.18 | $290k | 204,936 | Jan 8, 2026 |
Questions about Khozema Shipchandler
Answered from the filings on this page, as of the latest one.
Is Khozema Shipchandler buying or selling?
In the last 12 months Khozema Shipchandler reported 0 open-market buys worth $0 and 10 open-market sells worth $38M on SEC Form 4; the latest was sold $4.2M of TWLO on Oct 5, 2026. Grants, option exercises and tax withholding are not counted.
How did Khozema Shipchandler's past buys perform?
Not measured yet. InsiderTell needs three past buys with six months of prices to publish a track record, and Khozema Shipchandler has 0.
Where does Khozema Shipchandler file Form 4?
Khozema Shipchandler has filed Form 4 at TWLO (TWILIO INC) as Chief Executive Officer; LIFE (Ethos Technologies Inc.). A Form 4 is required of officers, directors and holders of more than 10% of a share class within two business days of a trade.
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.