Twilio CEO exercises options and sells 32,158 shares
Twilio Inc.’s CEO Khozema Shipchandler reported an option exercise and related share sales.
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Form Type
4
Rhea-AI Filing Summary
Twilio Inc.’s CEO Khozema Shipchandler reported an option exercise and related share sales. On May 26, 2026, he exercised an employee stock option to acquire 32,158 shares of Class A common stock at an exercise price of $76.63 per share, from a fully vested option grant.
On the same date, he sold 32,158 Class A shares in multiple open‑market transactions at weighted average prices ranging from about $180.36 to $188.00 per share, pursuant to a Rule 10b5‑1 trading plan dated February 18, 2026. Following these transactions, he directly held 235,542 Class A shares, and a portion of his holdings consists of restricted stock units, each representing one share upon settlement.
Insights
Pre‑planned option exercise and same‑day sale, leaving CEO with a sizable remaining stake.
The data shows Khozema Shipchandler exercised 32,158 employee stock options at an exercise price of $76.63 and sold an equal number of Class A shares in open‑market trades on May 26, 2026. This is a classic exercise‑and‑sell pattern, monetizing options rather than increasing net share ownership.
Footnotes state both the exercise and sales were executed under a Rule 10b5‑1 trading plan dated February 18, 2026, indicating the trades were pre‑scheduled. After these transactions, he directly held 267,700 Class A shares, and some holdings are in the form of RSUs that convert into shares one‑for‑one, so he maintains a substantial equity position.
Insider Trade Summary 10b5-1
Exercise and Sale: 32,158 shares ($3.51M approx. pre-tax spread)
Exercise and Sale
10 txns
Insider
Shipchandler Khozema
Role
Chief Executive Officer
Sold
32,158 shs ($5.97M)
Approx. gross sale proceeds
$5.97M
Approx. exercise cost
$2.46M
Approx. pre-tax spread
$3.51M
| Type | Security | Shares | Price | Value |
|---|---|---|---|---|
| Exercise | Employee Stock Option (right to buy) | 32,158 | $0.00 | $0.00 |
| Exercise | Class A Common Stock | 32,158 | $76.63 | $2.46M |
| Sale | Class A Common Stock | 927 | $180.7018 | $168K |
| Sale | Class A Common Stock | 2,084 | $181.9606 | $379K |
| Sale | Class A Common Stock | 2,677 | $182.7546 | $489K |
| Sale | Class A Common Stock | 3,986 | $184.5514 | $736K |
| Sale | Class A Common Stock | 4,524 | $185.1502 | $838K |
| Sale | Class A Common Stock | 4,719 | $186.5475 | $880K |
| Sale | Class A Common Stock | 8,772 | $187.1872 | $1.64M |
| Sale | Class A Common Stock | 4,469 | $188.00 | $840K |
Holdings After Transaction:
Employee Stock Option (right to buy) — 3,260 contracts (Direct);
Class A Common Stock — 235,542 shares (Direct)
Footnotes (11)
- F1. The exercise reported was executed under the Reporting Person's 10b5-1 trading plan, dated as of 2/18/2026.
- F2. A portion of these shares represent Restricted Stock Units ("RSUs"). Each RSU represents a contingent right to receive one share of the Issuer's Class A common stock.
- F3. The sales reported were executed under the Reporting Person's 10b5-1 trading plan, dated as of 2/18/2026.
- F4. The reported price in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $180.36 to $181.31 per share, inclusive. The Reporting Person undertakes to provide to the Issuer, any security holder of the Issuer, or to the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the range set forth in this footnote.
- F5. The reported price in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $181.46 to $182.455 per share, inclusive. The Reporting Person undertakes to provide to the Issuer, any security holder of the Issuer, or to the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the range set forth in this footnote.
- F6. The reported price in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $182.465 to $183.40 per share, inclusive. The Reporting Person undertakes to provide to the Issuer, any security holder of the Issuer, or to the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the range set forth in this footnote.
- F7. The reported price in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $183.81 to $184.805 per share, inclusive. The Reporting Person undertakes to provide to the Issuer, any security holder of the Issuer, or to the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the range set forth in this footnote.
- F8. The reported price in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $184.815 to $185.80 per share, inclusive. The Reporting Person undertakes to provide to the Issuer, any security holder of the Issuer, or to the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the range set forth in this footnote.
- F9. The reported price in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $185.94 to $186.925 per share, inclusive. The Reporting Person undertakes to provide to the Issuer, any security holder of the Issuer, or to the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the range set forth in this footnote.
- F10. The reported price in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $186.94 to $187.62 per share, inclusive. The Reporting Person undertakes to provide to the Issuer, any security holder of the Issuer, or to the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each separate price within the range set forth in this footnote.
- F11. The shares underlying the option are fully vested and exercisable.
Key Figures
Options exercised: 32,158 shares
Exercise price: $76.63 per share
Shares sold: 32,158 shares
+5 more
8 metrics
Options exercised
32,158 shares
Employee stock option exercise on May 26, 2026
Exercise price
$76.63 per share
Employee stock option for Class A common stock
Shares sold
32,158 shares
Open-market sales on May 26, 2026
Highest reported sale price
$188.00 per share
Class A common stock open-market sale bucket
Lowest reported sale price range
$180.36–$181.31
Weighted-average sale price range in one transaction group
Post-transaction holdings
267,700 shares
Direct Class A holdings after May 26, 2026 transactions
10b5-1 plan date
February 18, 2026
Plan governing exercise and sales
Option expiration
October 31, 2028
Expiration date of exercised employee stock option grant
Key Terms
Rule 10b5-1 trading plan, Restricted Stock Units ("RSUs"), Employee Stock Option (right to buy), weighted average price, +1 more
5 terms
Rule 10b5-1 trading plan regulatory
"The exercise reported was executed under the Reporting Person's 10b5-1 trading plan, dated as of 2/18/2026."
A Rule 10b5-1 trading plan is a pre-arranged schedule that allows company insiders to buy or sell stock at specific times, even if they have inside information. It helps prevent accusations of unfair trading by making these transactions look planned and transparent, rather than sneaky or illegal.
Restricted Stock Units ("RSUs") financial
"A portion of these shares represent Restricted Stock Units ("RSUs"). Each RSU represents a contingent right to receive one share..."
Restricted stock units (RSUs) are a company promise to give an employee shares of stock (or cash equivalent) in the future, but only after certain conditions—usually staying with the company for a set time or hitting performance goals—are met. Investors watch RSUs because when they vest they increase the number of shares outstanding and can lead insiders to sell shares, affecting share price, company dilution and the true cost of employee pay.
Employee Stock Option (right to buy) financial
"security_title: "Employee Stock Option (right to buy)" with underlying Class A Common Stock"
weighted average price financial
"The reported price in Column 4 is a weighted average price. These shares were sold in multiple transactions..."
Weighted average price is the average price of a security where each trade or component is counted according to its size, so bigger trades pull the average more than smaller ones. Think of it like calculating the average cost of a grocery haul where items you bought more of have greater influence on the final per-item cost. Investors use it to understand the true average price paid or received, judge execution quality, and compare trading performance against market movement.
fully vested and exercisable financial
"The shares underlying the option are fully vested and exercisable."
FAQ
AI-generated questions and answers. How Rhea-AI works. Not financial advice.
What did Twilio (TWLO) CEO Khozema Shipchandler report in this Form 4?
He reported exercising 32,158 employee stock options and selling 32,158 Class A shares on May 26, 2026. The transactions were structured as an option exercise followed by multiple open‑market sales executed the same day.
At what price did the Twilio CEO exercise his stock options in this filing?
He exercised an employee stock option for 32,158 shares of Class A common stock at an exercise price of $76.63 per share. The filing notes that the underlying option was fully vested and exercisable at the time of the transaction.
Were the Twilio (TWLO) CEO’s trades made under a Rule 10b5-1 plan?
Yes. Footnotes state that both the option exercise and the reported sales were executed under Khozema Shipchandler’s Rule 10b5‑1 trading plan dated February 18, 2026, indicating the trades were pre‑arranged rather than discretionary market‑timing decisions.
Does the Twilio Form 4 mention restricted stock units (RSUs)?
Yes. A footnote explains that a portion of the reported holdings represents restricted stock units, or RSUs. Each RSU gives the holder a contingent right to receive one share of Twilio’s Class A common stock upon satisfaction of applicable vesting or settlement conditions.
AI-generated analysis. How Rhea-AI works. Not financial advice.
