Twilio officer proposes $4.2M sale of 14,442 shares

Two earlier sales are also reported: 14,458 shares on July 6, 2026, and 13,898 shares on September 30, 2026.

Rhea-AI Filing Summary

Twilio Inc. reports that Khozema Shipchandler, identified as an officer and director, intends to sell 14,442 shares of common stock, with an approximate sale date of October 5, 2026. Charles Schwab & Co., Inc. is listed as broker, and NYSE as the exchange. The reported aggregate market value is $4,203,120.00; the shares are listed in connection with a restricted stock lapse on September 30, 2026. The notice lists 153,575,220 shares outstanding.

Key Figures

Shares to be sold: 14,442 shares Aggregate market value: $4,203,120.00 Shares outstanding: 153,575,220 shares +4 more

7 metrics

Shares to be sold 14,442 shares Approximate sale date October 5, 2026

Aggregate market value $4,203,120.00 Shares proposed for sale

Shares outstanding 153,575,220 shares Outstanding shares figure reported with the proposed sale

Prior shares sold 14,458 shares July 6, 2026

Prior-sale aggregate market value $3,042,343.00 Sale reported for July 6, 2026

Prior shares sold 13,898 shares September 30, 2026

Prior-sale aggregate market value $4,087,133.00 Sale reported for September 30, 2026

Key Terms

Rule 144, Restricted Stock Lapse, Equity Compensation

3 terms

Rule 144 regulatory

"paragraph (a) of Rule 144"

Rule 144 is a U.S. securities regulation that sets conditions under which restricted or insider-held shares can be legally resold to the public, such as required holding periods, availability of public information, limits on how much can be sold at once, and certain filing requirements. For investors it matters because it determines when previously locked-up shares can enter the market — like a release valve that can increase supply, affect share price, and signal insider intent.

Restricted Stock Lapse financial

"Restricted Stock Lapse"

Equity Compensation financial

"Equity Compensation"

Equity compensation is pay given to employees, executives or contractors in the form of company ownership—such as stock, stock options or restricted shares—rather than just cash. It matters to investors because it can align workers' incentives with shareholders (like paying someone in slices of the same pie they help grow), but it also increases the number of shares outstanding and company expenses, affecting ownership percentages and earnings per share.

FAQ

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

How many TWLO shares does Khozema Shipchandler intend to sell?

Khozema Shipchandler intends to sell 14,442 shares of Twilio common stock. The approximate sale date is October 5, 2026, and the reported aggregate market value is $4,203,120.00.

What TWLO shares did Khozema Shipchandler sell in the prior three months?

The reported prior sales were 14,458 shares on July 6, 2026, with an aggregate market value of $3,042,343.00, and 13,898 shares on September 30, 2026, with an aggregate market value of $4,087,133.00.

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

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Available on EDGAR 10/05/2026 - 04:06 PM Accepted by SEC EDGAR 10/05/2026 - 04:06 PM Learn about SEC filing dates

Form 144 Filer Information	UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Form 144 NOTICE OF PROPOSED SALE OF SECURITIES PURSUANT TO RULE 144 UNDER THE SECURITIES ACT OF 1933
FORM 144

144: Filer Information

Filer CIK	0001737610
Filer CCC	XXXXXXXX
Is this a LIVE or TEST Filing?	LIVE TEST
Submission Contact Information
Name
Phone
E-Mail Address

144: Issuer Information

Name of Issuer	TWILIO INC
SEC File Number	001-37806
Address of Issuer	101 SPEAR STREET SUITE 500 San Francisco CALIFORNIA 94105
Phone	415-390-2337
Name of Person for Whose Account the Securities are To Be Sold	Shipchandler Khozema
See the definition of "person" in paragraph (a) of Rule 144. Information is to be given not only as to the person for whose account the securities are to be sold but also as to all other persons included in that definition. In addition, information shall be given as to sales by all persons whose sales are required by paragraph (e) of Rule 144 to be aggregated with sales for the account of the person filing this notice.
Relationship to Issuer	Officer
Relationship to Issuer	Director

144: Securities Information

Title of the Class of Securities To Be Sold	Name and Address of the Broker	Number of Shares or Other Units To Be Sold	Aggregate Market Value	Number of Shares or Other Units Outstanding	Approximate Date of Sale	Name the Securities Exchange
Common	Charles Schwab & Co., Inc. 3000 Schwab Way Westlake TX 76262	14442	4203120.00	153575220	10/05/2026	NYSE

Furnish the following information with respect to the acquisition of the securities to be sold and with respect to the payment of all or any part of the purchase price or other consideration therefor:

144: Securities To Be Sold

Title of the Class	Date you Acquired	Nature of Acquisition Transaction	Name of Person from Whom Acquired	Is this a Gift?	Date Donor Acquired	Amount of Securities Acquired	Date of Payment	Nature of Payment *
Common	09/30/2026	Restricted Stock Lapse	TWILIO INC.			14442	09/30/2026	Equity Compensation

* If the securities were purchased and full payment therefor was not made in cash at the time of purchase, explain in the table or in a note thereto the nature of the consideration given. If the consideration consisted of any note or other obligation, or if payment was made in installments describe the arrangement and state when the note or other obligation was discharged in full or the last installment paid.

Furnish the following information as to all securities of the issuer sold during the past 3 months by the person for whose account the securities are to be sold.

144: Securities Sold During The Past 3 Months

Name and Address of Seller	Title of Securities Sold	Date of Sale	Amount of Securities Sold	Gross Proceeds
Khozema Shipchandler 101 SPEAR STREET, SUITE 500 SAN FRANCISCO CA 94105	TWILIO INC	07/06/2026	14458	3042343.00
Khozema Shipchandler 101 SPEAR STREET, SUITE 500 SAN FRANCISCO CA 94105	TWILIO INC	09/30/2026	13898	4087133.00

144: Remarks and Signature

Remarks
Date of Notice	10/05/2026
Date of Plan Adoption or Giving of Instruction, If Relying on Rule 10b5-1	02/18/2026
ATTENTION:
The person for whose account the securities to which this notice relates are to be sold hereby represents by signing this notice that he does not know any material adverse information in regard to the current and prospective operations of the Issuer of the securities to be sold which has not been publicly disclosed. If such person has adopted a written trading plan or given trading instructions to satisfy Rule 10b5-1 under the Exchange Act, by signing the form and indicating the date that the plan was adopted or the instruction given, that person makes such representation as of the plan adoption or instruction date.
Signature	Khozema Shipchandler
ATTENTION: Intentional misstatements or omission of facts constitute Federal Criminal Violations (See 18 U.S.C. 1001)