Twilio (NYSE: TWLO) CEO uses 10b5-1 plan to exercise options and sell 32,158 shares

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 267,700 Class A shares, and a portion of his holdings consists of restricted stock units, each representing one share upon settlement.

Insights

Equity compensation analyst

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

Net Seller: 32,158 shares ($5,971,688)

Net Sell 10 txns

Insider Shipchandler Khozema

Role Chief Executive Officer

Sold 32,158 shs ($5.97M)

Type	Security	Shares	Price	Value
Exercise	Employee Stock Option (right to buy)	32,158	$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 shares (Direct, null); Class A Common Stock — 267,700 shares (Direct, null)

Footnotes (1)

1. The exercise reported was executed under the Reporting Person's 10b5-1 trading plan, dated as of 2/18/2026. 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. The sales reported were executed under the Reporting Person's 10b5-1 trading plan, dated as of 2/18/2026. 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. 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. 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. 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. 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. 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. 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. 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."

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Form 4 Insider Transactions: What Each Field Means →

Available on EDGAR 05/28/2026 - 04:32 PM Accepted by SEC EDGAR 05/28/2026 - 04:31 PM Learn about SEC filing dates

SEC Form 4

FORM 4

UNITED STATES SECURITIES AND EXCHANGE COMMISSION
Washington, D.C. 20549

STATEMENT OF CHANGES IN BENEFICIAL OWNERSHIP

Filed pursuant to Section 16(a) of the Securities Exchange Act of 1934
or Section 30(h) of the Investment Company Act of 1940

OMB APPROVAL

OMB Number:			3235-0287
Estimated average burden
hours per response:			0.5

Check this box if no longer subject to Section 16. Form 4 or Form 5 obligations may continue. See Instruction 1(b).

X

Check this box to indicate that a transaction was made pursuant to a contract, instruction or written plan for the purchase or sale of equity securities of the issuer that is intended to satisfy the affirmative defense conditions of Rule 10b5-1(c). See Instruction 10.

1. Name and Address of Reporting Person^*

Shipchandler Khozema

(Last) (First) (Middle)

101 SPEAR STREET, FIFTH FLOOR

(Street)

SAN FRANCISCO CALIFORNIA 94105

(City) (State) (Zip)

UNITED STATES

(Country)

2. Issuer Name and Ticker or Trading Symbol
TWILIO INC [ TWLO ]

5. Relationship of Reporting Person(s) to Issuer
(Check all applicable)

X	Director		10% Owner
X	Officer (give title below)		Other (specify below)
	Chief Executive Officer

2a. Foreign Trading Symbol

3. Date of Earliest Transaction (Month/Day/Year)
05/26/2026

6. Individual or Joint/Group Filing (Check Applicable Line)

X	Form filed by One Reporting Person
	Form filed by More than One Reporting Person

4. If Amendment, Date of Original Filed (Month/Day/Year)

Table I - Non-Derivative Securities Acquired, Disposed of, or Beneficially Owned
1. Title of Security (Instr. 3)	2. Transaction Date (Month/Day/Year)	2A. Deemed Execution Date, if any (Month/Day/Year)	3. Transaction Code (Instr. 8)		4. Securities Acquired (A) or Disposed Of (D) (Instr. 3, 4 and 5)			5. Amount of Securities Beneficially Owned Following Reported Transaction(s) (Instr. 3 and 4)	6. Ownership Form: Direct (D) or Indirect (I) (Instr. 4)	7. Nature of Indirect Beneficial Ownership (Instr. 4)
			Code	V	Amount	(A) or (D)	Price
Class A Common Stock	05/26/2026		M(1)		32,158	A	$76.63	267,700(2)	D
Class A Common Stock	05/26/2026		S(3)		927	D	$180.7018(4)	266,773(2)	D
Class A Common Stock	05/26/2026		S(3)		2,084	D	$181.9606(5)	264,689(2)	D
Class A Common Stock	05/26/2026		S(3)		2,677	D	$182.7546(6)	262,012(2)	D
Class A Common Stock	05/26/2026		S(3)		3,986	D	$184.5514(7)	258,026(2)	D
Class A Common Stock	05/26/2026		S(3)		4,524	D	$185.1502(8)	253,502(2)	D
Class A Common Stock	05/26/2026		S(3)		4,719	D	$186.5475(9)	248,783(2)	D
Class A Common Stock	05/26/2026		S(3)		8,772	D	$187.1872(10)	240,011(2)	D
Class A Common Stock	05/26/2026		S(3)		4,469	D	$188	235,542(2)	D

Table II - Derivative Securities Acquired, Disposed of, or Beneficially Owned (e.g., puts, calls, warrants, options, convertible securities)
1. Title of Derivative Security (Instr. 3)	2. Conversion or Exercise Price of Derivative Security	3. Transaction Date (Month/Day/Year)	3A. Deemed Execution Date, if any (Month/Day/Year)	4. Transaction Code (Instr. 8)		5. Number of Derivative Securities Acquired (A) or Disposed of (D) (Instr. 3, 4 and 5)		6. Date Exercisable and Expiration Date (Month/Day/Year)		7. Title and Amount of Securities Underlying Derivative Security (Instr. 3 and 4)		8. Price of Derivative Security (Instr. 5)	9. Number of derivative Securities Beneficially Owned Following Reported Transaction(s) (Instr. 4)	10. Ownership Form: Direct (D) or Indirect (I) (Instr. 4)	11. Nature of Indirect Beneficial Ownership (Instr. 4)
				Code	V	(A)	(D)	Date Exercisable	Expiration Date	Title	Amount or Number of Shares
Employee Stock Option (right to buy)	$76.63	05/26/2026		M(1)			32,158	(11)	10/31/2028	Class A Common Stock	32,158	$0	3,260	D

Explanation of Responses:

1. The exercise reported was executed under the Reporting Person's 10b5-1 trading plan, dated as of 2/18/2026.

2. 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.

3. The sales reported were executed under the Reporting Person's 10b5-1 trading plan, dated as of 2/18/2026.

4. 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.

5. 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.

6. 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.

7. 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.

8. 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.

9. 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.

10. 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.

11. The shares underlying the option are fully vested and exercisable.

Remarks:

	/s/ Juliana Chen as attorney-in-fact for Reporting Person	05/28/2026
	** Signature of Reporting Person	Date
Reminder: Report on a separate line for each class of securities beneficially owned directly or indirectly.
* If the form is filed by more than one reporting person, see Instruction 4 (b)(v).
** Intentional misstatements or omissions of facts constitute Federal Criminal Violations See 18 U.S.C. 1001 and 15 U.S.C. 78ff(a).
Note: File three copies of this Form, one of which must be manually signed. If space is insufficient, see Instruction 6 for procedure.
Persons who respond to the collection of information contained in this form are not required to respond unless the form displays a currently valid OMB Number.
* Form 4: SEC 1474 (03-26)

FAQ

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.

How many Twilio (TWLO) shares did the CEO sell and at what prices?

He sold 32,158 Class A shares in multiple open‑market trades. Weighted average sale prices ranged roughly from $180.36 to $188.00 per share, with each transaction bucket disclosing a specific weighted average and an underlying price range for individual trades.

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.

How many Twilio shares does the CEO hold after these transactions?

After completing the May 26, 2026 exercise and related sales, he directly held 267,700 shares of Twilio Class A common stock. The filing also notes that a portion of his position consists of restricted stock units that each convert into one Class A share.

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.