Twilio (NYSE: TWLO) CEO sells 13,881 shares, retains large stake

Filing Impact

(Very High)

Filing Sentiment

(Negative)

Form Type

Rhea-AI Filing Summary

Twilio Inc. Chief Executive Officer Khozema Shipchandler reported multiple open-market sales of Class A common stock. On June 30, 2026, he sold a total of 13,881 shares in several transactions at prices around $200 per share.

According to a footnote, certain shares were sold to cover statutory tax withholding obligations tied to vesting restricted stock units under Twilio’s equity incentive plans, meaning those sales were not fully discretionary. After these transactions, Shipchandler directly holds 221,661 shares of Twilio Class A common stock.

Insider Trade Summary

Net Seller: 13,881 shares ($2,793,699)

Net Sell 6 txns

Insider Shipchandler Khozema

Role Chief Executive Officer

Sold 13,881 shs ($2.79M)

Type	Security	Shares	Price	Value
Sale	Class A Common Stock	1,950	$199.2362	$389K
Sale	Class A Common Stock	3,231	$200.2039	$647K
Sale	Class A Common Stock	4,286	$201.2606	$863K
Sale	Class A Common Stock	1,560	$202.4916	$316K
Sale	Class A Common Stock	2,780	$203.1482	$565K
Sale	Class A Common Stock	74	$203.885	$15K

Holdings After Transaction: Class A Common Stock — 233,592 shares (Direct, null)

Footnotes (1)

Represents the number of shares sold to cover the statutory tax withholding obligations in connection with the vesting of Restricted Stock Units ("RSUs"). This sale is mandated by the Issuer's election under its equity incentive plans to require the satisfaction of minimum statutory tax withholding obligations to be funded by a "sell-to-cover" transaction and does not represent a discretionary sale by the Reporting Person. The reported price in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $198.7850 to $199.64 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. A portion of these shares represent RSUs. Each RSU represents a contingent right to receive one share of the Issuer's Class A common stock. The reported price in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $199.78 to $200.7150 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 $200.8150 to $201.7450 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 $201.84 to $202.8350 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 $202.85 to $203.66 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.

Key Figures

Shares sold: 13,881 shares Highest reported sale price: $203.8850 per share Lowest price range bound: $198.7850 per share +3 more

6 metrics

Shares sold 13,881 shares Total net shares sold on June 30, 2026

Highest reported sale price $203.8850 per share Weighted average price for one sale tranche

Lowest price range bound $198.7850 per share Lower end of disclosed sale price ranges

Post-transaction holdings 221,661 shares Class A shares directly owned after reported sales

Individual trade sizes 74 to 4,286 shares Range of share counts per reported sale

Net buy/sell direction -13,881 shares Net-sell across all reported June 30 transactions

Key Terms

Restricted Stock Units ("RSUs"), sell-to-cover, weighted average price, equity incentive plans, +1 more

5 terms

Restricted Stock Units ("RSUs") financial

"in connection with the vesting of 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.

sell-to-cover financial

"to be funded by a "sell-to-cover" transaction and does not represent"

Sell-to-cover is when part of newly issued or exercised company stock is immediately sold to pay required taxes and fees, so the recipient keeps the remaining shares. For investors this matters because it reduces the number of shares insiders or employees actually hold after a grant, can create small, routine share sales that aren’t signal of cashing out, and slightly increases share supply on the market—like selling a portion of a paycheck to cover the tax bill.

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.

equity incentive plans financial

"mandated by the Issuer's election under its equity incentive plans"

Equity incentive plans are company programs that pay employees, executives, or directors with company stock, stock options, or share units instead of or in addition to cash, aiming to align their interests with shareholders—like giving team members a stake in the house they help build. For investors this matters because such plans can motivate better company performance but also dilute existing ownership and increase reported compensation costs, so they affect future earnings, voting power, and share value.

open market or private transaction financial

"Sale in open market or private transaction"

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Form 4 Insider Transactions: What Each Field Means →

Available on EDGAR 07/02/2026 - 04:24 PM Accepted by SEC EDGAR 07/02/2026 - 04:24 PM

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).

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)
06/30/2026

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)
1. Title of Security (Instr. 3)	2. Transaction Date (Month/Day/Year)	2A. Deemed Execution Date, if any (Month/Day/Year)	Code	V	Amount	(A) or (D)	Price		6. Ownership Form: Direct (D) or Indirect (I) (Instr. 4)	7. Nature of Indirect Beneficial Ownership (Instr. 4)
Class A Common Stock	06/30/2026		S		1,950⁽¹⁾	D	$199.2362⁽²⁾	233,592⁽³⁾	D
Class A Common Stock	06/30/2026		S		3,231⁽¹⁾	D	$200.2039⁽⁴⁾	230,361⁽³⁾	D
Class A Common Stock	06/30/2026		S		4,286⁽¹⁾	D	$201.2606⁽⁵⁾	226,075⁽³⁾	D
Class A Common Stock	06/30/2026		S		1,560⁽¹⁾	D	$202.4916⁽⁶⁾	224,515⁽³⁾	D
Class A Common Stock	06/30/2026		S		2,780⁽¹⁾	D	$203.1482⁽⁷⁾	221,735⁽³⁾	D
Class A Common Stock	06/30/2026		S		74⁽¹⁾	D	$203.885	221,661⁽³⁾	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)
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)	Code	V	(A)	(D)	Date Exercisable	Expiration Date	Title	Amount or Number of Shares	8. Price of Derivative Security (Instr. 5)		10. Ownership Form: Direct (D) or Indirect (I) (Instr. 4)	11. Nature of Indirect Beneficial Ownership (Instr. 4)

Explanation of Responses:

1. Represents the number of shares sold to cover the statutory tax withholding obligations in connection with the vesting of Restricted Stock Units ("RSUs"). This sale is mandated by the Issuer's election under its equity incentive plans to require the satisfaction of minimum statutory tax withholding obligations to be funded by a "sell-to-cover" transaction and does not represent a discretionary sale by the Reporting Person.

2. The reported price in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $198.7850 to $199.64 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.

3. A portion of these shares represent RSUs. Each RSU represents a contingent right to receive one share of the Issuer's Class A common stock.

4. The reported price in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $199.78 to $200.7150 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 $200.8150 to $201.7450 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 $201.84 to $202.8350 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 $202.85 to $203.66 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.

Remarks:

	/s/ Juliana Chen as attorney-in-fact for Reporting Person	07/02/2026
	** 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)

Source: View Original Filing on SEC EDGAR

FAQ

What insider transaction did Twilio (TWLO) disclose for its CEO?

Twilio disclosed that CEO Khozema Shipchandler reported open-market sales of 13,881 shares of Class A common stock. The trades occurred on June 30, 2026, across multiple price points, and were detailed in a Form 4 insider transaction filing.

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

Khozema Shipchandler sold 13,881 Twilio Class A shares in several transactions. Reported weighted average prices for these trades ranged from about $198.79 to $203.89 per share, based on multiple executions within specified price ranges disclosed in the filing footnotes.

Why were some of the Twilio (TWLO) CEO’s shares sold on June 30, 2026?

A filing footnote explains that some shares were sold to cover statutory tax withholding obligations from vesting restricted stock units. Twilio’s equity incentive plans mandate a sell-to-cover transaction for minimum statutory taxes, so those sales were not purely discretionary trades by the CEO.

How many Twilio (TWLO) shares does the CEO hold after the reported sales?

Following the reported June 30, 2026 transactions, CEO Khozema Shipchandler directly holds 221,661 shares of Twilio Class A common stock. This post-transaction holding amount is disclosed in the Form 4 as the total number of shares beneficially owned after the sales.

What does the Form 4 say about the nature of Twilio (TWLO) CEO’s June 30 trades?

Each transaction is coded as an open-market sale of non-derivative Class A common stock. A key footnote clarifies that shares sold to satisfy RSU tax withholding obligations were mandated by Twilio’s equity plans, differentiating them from fully discretionary portfolio sales.

Were the Twilio (TWLO) CEO’s June 30, 2026 sales linked to options or derivatives?

No derivative exercises are shown in the summary; all reported trades involve non-derivative Class A common stock. The filing’s derivative position summary is empty, indicating no option or other derivative transactions were reported in connection with these June 30, 2026 sales.