Twilio CEO sells 12,922 shares under 10b5-1 plan

Rhea-AI Filing Summary

Twilio Inc Chief Executive Officer Khozema Shipchandler reported selling a total of 12,922 shares of Class A Common Stock on October 3, 2025, in open-market or private transactions at weighted average prices of $103.3009 and $104.3732 per share under a Rule 10b5-1 trading plan dated February 24, 2025. Following these sales, he directly holds 220,383 shares of Twilio Class A Common Stock.

Insights

Corporate Governance Analyst

Insider sales followed an established 10b5-1 plan; disclosure is thorough.

The reported transactions show that the reporting person used a 10b5-1 plan dated 2/24/2025 to sell a total of 12,922 shares on 10/03/2025, with weighted average prices of $103.3009 and $104.3732. Using a pre-set plan typically indicates the trades were formulaic rather than opportunistic.

Risks and dependencies include timing and size relative to total holdings and potential market perception; monitor any subsequent filings that change beneficial ownership materially within the next 90 days.

Executive Compensation Analyst

Sales included shares tied to RSUs, showing routine vesting and liquidity management.

The filing states that part of the sold shares represented Restricted Stock Units (RSUs), each convertible into one Class A share, indicating these transactions may be driven by vesting schedules or tax-liability events rather than a change in view of company prospects.

Watch for future filings showing changes in RSU vesting, additional 10b5-1 plans, or large option exercises over the next 6 months that could further affect reported ownership.

Insider Trade Summary

Net Seller: 12,922 shares

Net Sell 2 txns

Insider Shipchandler Khozema

Role Chief Executive Officer

Sold 12,922 shs ($1.34M)

Type	Security	Shares	Price	Value
Sale	Class A Common Stock	3,462	$103.3009	$358K
Sale	Class A Common Stock	9,460	$104.3732	$987K

Holdings After Transaction: Class A Common Stock — 220,383 shares (Direct)

Footnotes (4)

1. F1. The sales reported were executed under the Reporting Person's 10b5-1 trading plan, dated as of 2/24/2025.
2. F2. The reported price in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $102.80 to $103.79 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. F3. 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.
4. F4. The reported price in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $103.83 to $104.74 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

Total shares sold: 12,922 shares First sale size: 3,462 shares Second sale size: 9,460 shares +5 more

8 metrics

Total shares sold 12,922 shares Aggregate Class A Common Stock sold on October 3, 2025

First sale size 3,462 shares Class A Common Stock sold with weighted average price $103.3009

Second sale size 9,460 shares Class A Common Stock sold with weighted average price $104.3732

Weighted average price 1 $103.3009 per share First reported sale of Class A Common Stock

Weighted average price 2 $104.3732 per share Second reported sale of Class A Common Stock

Price range 1 $102.80–$103.79 per share Range of prices for one set of weighted average sales

Price range 2 $103.83–$104.74 per share Range of prices for another set of weighted average sales

Post-transaction direct holdings 220,383 shares Direct Class A Common Stock held after reported transactions

Key Terms

Rule 10b5-1 trading plan, Restricted Stock Units ("RSUs"), weighted average price

3 terms

Rule 10b5-1 trading plan regulatory

"The sales reported were executed under the Reporting Person's 10b5-1 trading plan"

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.

FAQ

AI-generated questions and answers. How Rhea-AI works. Not financial advice.

What did Twilio (TWLO) CEO Khozema Shipchandler report selling in this Form 4?

Khozema Shipchandler, Twilio's Chief Executive Officer, reported selling 12,922 shares of Class A Common Stock. These sales were executed on October 3, 2025 at weighted average prices of $103.3009 and $104.3732 per share under a pre-established Rule 10b5-1 trading plan.

On what date did the TWLO insider transactions occur and at what prices?

The reported Twilio (TWLO) insider transactions occurred on October 3, 2025. Two sale tranches were reported with weighted average prices of $103.3009 and $104.3732 per share, with underlying trades executed within disclosed ranges between $102.80 and $104.74 per share.

Was the Twilio (TWLO) CEO's sale made under a Rule 10b5-1 plan?

Yes. A footnote states the sales were executed under the Reporting Person's Rule 10b5-1 trading plan dated February 24, 2025. Such plans allow pre-arranged trading independent of day-to-day market decisions, which can affect how investors interpret the timing of these transactions.

How many Twilio (TWLO) shares does Khozema Shipchandler hold after this sale?

After the reported sales, Khozema Shipchandler directly holds 220,383 shares of Twilio Class A Common Stock. A footnote also notes that a portion of the reported shares represent Restricted Stock Units ("RSUs"), each RSU being a contingent right to receive one share.

What type of security did the Twilio (TWLO) CEO sell in this Form 4 filing?

The transactions involve Class A Common Stock of Twilio (TWLO). Both entries are coded "S," indicating sales in open market or private transactions. They are non-derivative securities rather than options or other derivative instruments, according to the Form 4 data.

What share price ranges were disclosed for the TWLO insider sales?

Footnotes explain that the reported per-share prices are weighted averages. The underlying trades were executed in ranges between $102.80 and $103.79 per share, and between $103.83 and $104.74 per share, across multiple individual sale transactions.

AI-generated analysis. How Rhea-AI works. Not financial advice.

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Accepted by SEC EDGAR 10/07/2025 - 06:15 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 CA 94105

(City) (State) (Zip)

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

3. Date of Earliest Transaction (Month/Day/Year)
10/03/2025

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

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

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

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	10/03/2025		S(1)		3,462	D	$103.3009(2)	229,843(3)	D
Class A Common Stock	10/03/2025		S(1)		9,460	D	$104.3732(4)	220,383(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)
				Code	V	(A)	(D)	Date Exercisable	Expiration Date	Title	Amount or Number of Shares

Explanation of Responses:

1. The sales reported were executed under the Reporting Person's 10b5-1 trading plan, dated as of 2/24/2025.

2. The reported price in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $102.80 to $103.79 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 Restricted Stock Units ("RSUs"). Each RSU represents a contingent right to receive one share of 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 $103.83 to $104.74 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	10/07/2025
	** 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.