Twilio (TWLO) CEO exercises options, sells 44,158 shares under 10b5-1

Rhea-AI Filing Summary

Twilio Inc. Chief Executive Officer Khozema Shipchandler reported an option exercise and related share sale. He exercised options for 44,158 shares of Class A common stock at an exercise price of $117.94 per share, converting an employee stock option that was fully vested and exercisable.

On the same date, he sold 44,158 Class A shares in open‑market transactions at a weighted average price of $235.8836 per share, with individual sales ranging from $235.88 to $236.21. These transactions were carried out under a Rule 10b5‑1 trading plan dated February 18, 2026. After the transactions, he directly owned 235,542 Class A shares.

Insights

Equity compensation and insider-transactions analyst

Routine CEO option exercise and planned sale under 10b5‑1 plan.

Twilio’s CEO exercised employee stock options for 44,158 Class A shares at an exercise price of $117.94, then sold the same number of shares at a weighted average of $235.8836. This is a classic exercise‑and‑sell pattern that converts an option award into cash.

The filing shows no remaining derivative holdings from this option grant, as the derivative position drops to zero after the exercise. Following the sale, Shipchandler still directly holds 235,542 Class A shares, indicating a continued equity stake.

Both the option exercise and the sales were executed pursuant to a Rule 10b5‑1 trading plan dated February 18, 2026, suggesting these were pre‑scheduled transactions rather than discretionary market‑timing decisions. The informational value of the timing is therefore limited.

Insider Trade Summary 10b5-1

Net Seller: 44,158 shares ($10,416,148)

Net Sell 3 txns

Insider Shipchandler Khozema

Role Chief Executive Officer

Sold 44,158 shs ($10.42M)

Type	Security	Shares	Price	Value
Exercise	Employee Stock Option (right to buy)	44,158	$0.00	--
Exercise	Class A Common Stock	44,158	$117.94	$5.21M
Sale	Class A Common Stock	44,158	$235.8836	$10.42M

Holdings After Transaction: Employee Stock Option (right to buy) — 0 shares (Direct, null); Class A Common Stock — 279,700 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 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 $235.88 to $236.21 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

Shares sold: 44,158 shares Sale price (weighted average): $235.8836 per share Exercise shares: 44,158 shares +3 more

6 metrics

Shares sold 44,158 shares Class A common stock sold in open market on 2026-06-04

Sale price (weighted average) $235.8836 per share Open-market sales of Class A common stock

Exercise shares 44,158 shares Employee stock option exercised for Class A common stock

Option exercise price $117.94 per share Exercise price of employee stock option

Shares held after transaction 235,542 shares Direct Class A holdings following transactions

Option expiration February 21, 2030 Original expiration date of exercised employee stock option

Key Terms

Rule 10b5-1 trading plan, Restricted Stock Units ("RSUs"), weighted average price, Employee Stock Option (right to buy), +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")."

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.

weighted average price financial

"The reported price in Column 4 is a weighted average price."

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.

Employee Stock Option (right to buy) financial

"Security title: Employee Stock Option (right to buy)."

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 →

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)
06/04/2026

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	06/04/2026		M(1)		44,158	A	$117.94	279,700(2)	D
Class A Common Stock	06/04/2026		S(3)		44,158	D	$235.8836(4)	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)	$117.94	06/04/2026		M(1)			44,158	(5)	02/21/2030	Class A Common Stock	44,158	$0	0	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 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 $235.88 to $236.21 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 shares underlying the option are fully vested and exercisable.

Remarks:

	/s/ Juliana Chen as attorney-in-fact for Reporting Person	06/08/2026
	** 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 insider transaction did Twilio (TWLO) CEO Khozema Shipchandler report?

Twilio CEO Khozema Shipchandler reported exercising options for 44,158 Class A shares, then selling 44,158 shares in open‑market trades. The exercise converted an employee stock option into stock, and the sale monetized those shares while leaving him with 235,542 shares directly owned.

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

He sold 44,158 shares of Twilio Class A common stock in open‑market transactions at a weighted average price of $235.8836 per share. Individual sale prices ranged from $235.88 to $236.21, according to the filing’s footnote describing the trade price range.

What options did the Twilio (TWLO) CEO exercise in this Form 4 filing?

The CEO exercised an employee stock option covering 44,158 shares of Class A common stock at an exercise price of $117.94 per share. The filing notes that the underlying option was fully vested and exercisable, and that no derivative shares remained from this grant after the exercise.

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

Following the reported option exercise and share sale, Khozema Shipchandler directly owns 235,542 shares of Twilio Class A common stock. This post‑transaction share count, disclosed in the Form 4, helps show that he retains a substantial equity interest in the company after monetizing part of his position.

Were the Twilio (TWLO) CEO’s trades made under a Rule 10b5-1 plan?

Yes. The filing states that both the option exercise and the related stock sales were executed under Khozema Shipchandler’s Rule 10b5‑1 trading plan dated February 18, 2026. Such pre‑arranged plans are designed to allow systematic selling and reduce concerns about discretionary trade timing.

Does the Twilio (TWLO) Form 4 mention Restricted Stock Units (RSUs)?

The filing notes that a portion of the CEO’s holdings represents Restricted Stock Units, or RSUs, each giving him a contingent right to receive one Twilio Class A share. This means some of his equity exposure comes from un-delivered share awards that convert into stock as vesting conditions are met.