Twilio insider files Form 144 for 13,681-share sale on NYSE

Rhea-AI Filing Summary

Form 144 notice for TWILIO INC (TWLO): An insider proposes to sell 13,681 common shares through Charles Schwab & Co., with an aggregate market value of $1,376,145 and an approximate sale date of 09/30/2025 on the NYSE. The shares were reported as acquired on 09/30/2025 via a restricted stock lapse from Twilio and are characterized as equity compensation. The filer also disclosed two recent sales in the past three months: 20,008 shares on 06/30/2025 for $2,491,592 and 13,595 shares on 07/03/2025 for $1,591,376. The notice includes the standard representation that the seller is not aware of undisclosed material adverse information.

Positive

• Proper disclosure of planned sale and broker details demonstrates compliance with securities rules
• Transaction arises from restricted stock lapse, indicating routine equity compensation monetization rather than emergency disposition

Negative

• Insider selling activity: combined recent sales and planned sale total meaningful cash proceeds (~$5.46 million), which may concern some investors regarding insider liquidity
• Concentration of sales by the named individual within a short period could attract investor attention even if not material to outstanding shares

Insights

Securities Analyst

TL;DR: Insider selling disclosed; recent past sales and planned sale are notable but not necessarily material versus total shares outstanding.

The filing reports an intended sale of 13,681 shares valued at $1.38 million and prior sales totaling 33,603 shares resulting in roughly $4.08 million in gross proceeds over two transactions. Relative to the issuer's reported 153,433,606 outstanding shares, these individual sales represent a small fraction of total equity, suggesting limited immediate market impact. The shares to be sold were acquired via restricted stock lapse and are tied to equity compensation, indicating routine unlocking and monetization of employee/shareholder holdings rather than forced disposition.

Corporate Governance Expert

TL;DR: The filer complied with disclosure requirements; multiple recent insider sales warrant attention to insider liquidity but do not imply undisclosed issues.

The Form 144 provides required broker and quantity details and a standard attestation about absence of material nonpublic information. The pattern—restricted stock lapse followed by sales—aligns with standard post-vesting selling. Investors may note the frequency and scale of sales by the named individual but the filing itself contains no statement of insider intent beyond the sale and no allegations of adverse company developments.

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

144: Issuer Information

Name of Issuer

SEC File Number

Address of Issuer

Phone

Name of Person for Whose Account the Securities are To Be Sold

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

Relationship to Issuer

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	13681	1376145.00	153433606	09/30/2025	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	09/30/2025	Restricted Stock Lapse - See Remarks	TWILIO INC.			13681	09/30/2025	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	06/30/2025	20008	2491592.00
Khozema Shipchandler 101 SPEAR STREET, SUITE 500 SAN FRANCISCO CA 94105	TWILIO INC	07/03/2025	13595	1591376.00

144: Remarks and Signature

Remarks

Date of Notice

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

ATTENTION: Intentional misstatements or omission of facts constitute Federal Criminal Violations (See 18 U.S.C. 1001)

FAQ

What does the Form 144 filed for TWLO disclose?

The filing discloses a proposed sale of 13,681 TWLO common shares through Charles Schwab with an aggregate market value of $1,376,145, dated for 09/30/2025 on the NYSE.

Who is selling the TWLO shares and how were they acquired?

The seller is listed as Khozema Shipchandler for recent past sales; the 13,681 shares to be sold were acquired from TWILIO INC on 09/30/2025 via a restricted stock lapse as equity compensation.

What prior insider sales were reported in the last three months?

Two prior sales were reported: 20,008 shares sold on 06/30/2025 for $2,491,592, and 13,595 shares sold on 07/03/2025 for $1,591,376.

Does the Form 144 indicate any undisclosed material information about Twilio?

No. The filer signed the standard representation stating they do not know of any material adverse information about the issuer that has not been publicly disclosed.

Where will the proposed sale be executed?

The proposed sale is to be executed on the NYSE through Charles Schwab & Co., Inc..