Twilio Form 144: Insider sales and cashless exercise

TWILIO INC. notifies the SEC of proposed and recent sales of Common Stock under Rule 144 and related employee option activity.

Rhea-AI Filing Summary

TWILIO INC. notifies the SEC of proposed and recent sales of Common Stock under Rule 144 and related employee option activity.

The filing lists a planned cashless exercise with broker payment on 05/26/2026 and reports two recent sales by Khozema Shipchandler: 12,624 shares on 03/31/2026 for $1,550,337.00 and 15,715 shares on 04/06/2026 for $2,096,193.00.

Insights

Securities Compliance Analyst

Rule 144 notice of proposed resale and recent insider dispositions.

The excerpt lists a cashless exercise with broker payment scheduled on 05/26/2026 and two executed dispositions by Khozema Shipchandler on 03/31/2026 and 04/06/2026 with stated share counts and proceeds. This is a routine disclosure under resale rules.

Timing and method are explicit in the excerpt; cash‑flow treatment shows proceeds amounts for the two past sales. Subsequent filings would confirm completion of the planned exercise and any additional distributions.

Key Figures

Planned cashless exercise date: 05/26/2026 Sale on 03/31/2026: 12,624 shares Sale on 04/06/2026: 15,715 shares

3 metrics

Planned cashless exercise date 05/26/2026 Broker payment for cashless exercise listed for Common Stock

Sale on 03/31/2026 12,624 shares Proceeds reported as $1,550,337.00 by Khozema Shipchandler

Sale on 04/06/2026 15,715 shares Proceeds reported as $2,096,193.00 by Khozema Shipchandler

Key Terms

Rule 144, cashless exercise, broker payment

3 terms

Rule 144 regulatory

"Securities To Be Sold / Securities Sold During The Past 3 Months"

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.

cashless exercise financial

"Broker Payment for Cashless Exercise on 05/26/2026"

A cashless exercise is a way for an option holder to convert stock options into actual shares without paying the purchase price in cash; instead they immediately give up a portion of the newly issued shares to cover the cost and any withholding taxes. Investors care because this process increases the number of shares available and can slightly dilute existing holdings, while also signaling how insiders or employees are realizing compensation without needing cash — similar to paying for a purchase by handing over part of what you just bought.

broker payment financial

"Broker Payment for Cashless Exercise"

FAQ

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

What does TWLO's Form 144 report?

It reports proposed and recent resale activity under resale rules. The filing lists a planned cashless exercise on 05/26/2026 and two recent sales by Khozema Shipchandler for $1,550,337.00 and $2,096,193.00 respectively.

How many shares did Khozema Shipchandler sell according to the filing?

The filing shows two sales: 12,624 shares on 03/31/2026 and 15,715 shares on 04/06/2026. Dollar proceeds for those dates are listed as $1,550,337.00 and $2,096,193.00.

What is a cashless exercise listed in the TWLO filing?

A cashless exercise is an option exercise where a broker covers the exercise cost by withholding or selling shares. The filing notes a broker payment for cashless exercise on 05/26/2026 for Common Stock.

Does the Form 144 show shares to be sold or already sold?

It lists both: a planned transaction (cashless exercise with broker payment on 05/26/2026) and past sales by Khozema Shipchandler on 03/31/2026 and 04/06/2026 with reported share counts and proceeds.

Where can investors find more details about these transactions for TWLO?

More details typically appear in subsequent SEC filings or broker confirmations. This excerpt provides dates, share counts, and proceeds for the two past sales and the planned cashless exercise on 05/26/2026.

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

See more from StockTitan in Google Search and AI answers. Adds StockTitan as a preferred source · opens Google

Add on Google Not now

Accepted by SEC EDGAR 05/26/2026 - 04:12 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	32158	5971687.00	151773860	05/26/2026	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	05/26/2026	Employee Stock Option Exercise	TWILIO INC.			32158	05/26/2026	Broker Payment for Cashless Exercise

* 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	03/31/2026	12624	1550337.00
Khozema Shipchandler 101 SPEAR STREET, SUITE 500 SAN FRANCISCO CA 94105	TWILIO INC	04/06/2026	15715	2096193.00

144: Remarks and Signature

Remarks
Date of Notice	05/26/2026
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)