[144] Wayfair Inc. SEC Filing

Rhea-AI Filing Summary

Form 144 highlights for Twilio Inc. (TWLO):

• An affiliated holder, identified as Khozema Shipchandler, has filed to sell 7,000 common shares through Charles Schwab & Co. on or about 30 June 2025.
• The proposed sale represents a market value of $872,011 versus 152.7 million shares outstanding, or roughly 0.005% of shares outstanding.
• The shares were acquired via equity-compensation restricted-stock lapses on 5 June 2020 (1,956 shares) and 31 Dec 2023 (5,044 shares).
• Recent insider activity: the same seller disposed of 12,056 shares on 31 Mar 2025 for $1.16 million and 14,545 shares on 3 Apr 2025 for $1.33 million.
• No adverse information about Twilio’s operations is disclosed; the filer attests to possessing no non-public material adverse data.

The filing is a compliance notice rather than a corporate action and does not change Twilio’s fundamentals, but sustained insider selling can influence investor sentiment.

Positive

• None.

Negative

• Repeated insider selling totalling over $2.3 million in Q2 2025 could dampen investor sentiment despite limited numerical impact.
• Lack of disclosed 10b5-1 plan date means shareholders cannot confirm that transactions are pre-arranged, potentially raising governance questions.

Insights

Securities Analyst

TL;DR Modest insider sale (7k shares, <0.01% float); limited direct financial impact, but follows two larger sales this quarter.

The proposed $0.87 million sale is immaterial relative to Twilio’s market cap and share count, so it should not alter valuation models. However, cumulative disposals of roughly 34,600 shares in Q2 2025 may raise questions about management’s confidence and could weigh on short-term sentiment, especially given Twilio’s ongoing strategic transition toward profitability. Volume and price levels of these trades align with routine liquidity events tied to equity compensation, so I view the disclosure as neutral from a fundamental standpoint.

Corporate Governance Expert

TL;DR Recurrent insider selling may signal reduced insider alignment, but the size is too small to be considered materially worrisome.

While insiders are entitled to monetize stock awards, governance best practices encourage transparent trading plans to mitigate perception risk. The filer cites no 10b5-1 plan adoption date in the form, leaving investors without assurance that sales are pre-scheduled. Given cumulative Q2 sales exceeding $2.3 million, stakeholders may wish to confirm whether a formal trading plan exists. Nevertheless, because the current sale equals only 0.005% of outstanding shares, I deem the impact low and primarily reputational.

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
Class A	Fidelity Brokerage Services LLC 900 Salem Street Smithfield RI 02917	22580	1174322.38	103657178	06/30/2025	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 *
Class A	01/01/2002	Founders Shares	Issuer			22580	01/01/2002	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
Shah Charitable Foundation 4 Copley Place Boston MA 02116	Class A	04/10/2025	4000	111200.00
Shah Charitable Foundation 4 Copley Place Boston MA 02116	Class A	05/12/2025	4000	152000.00
Niraj S. Shah 4 Copley Place Boston MA 02116	Class A	05/12/2025	9527	381415.80
Niraj S. Shah 4 Copley Place Boston MA 02116	Class A	05/13/2025	5725	229565.57
Niraj S. Shah 4 Copley Place Boston MA 02116	Class A	05/14/2025	2258	90332.70
Niraj S. Shah 4 Copley Place Boston MA 02116	Class A	05/27/2025	72490	2928191.22
Shah Charitable Foundation 4 Copley Place Boston MA 02116	Class A	06/10/2025	4000	190400.00
Niraj S. Shah 4 Copley Place Boston MA 02116	Class A	06/20/2025	30000	1482829.96

144: Remarks and Signature

Remarks

Date of Notice

Date of Plan Adoption or Giving of Instruction, If Relying on Rule 10b5-1

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

How many Twilio (TWLO) shares are being sold under this Form 144?

The filing covers the proposed sale of 7,000 common shares.

What is the market value of the proposed TWLO share sale?

At the time of filing, the aggregate market value is approximately $872,011.

When is the planned sale date for the 7,000 TWLO shares?

The filer lists an approximate sale date of 30 June 2025.

How significant is this sale relative to Twilio’s total shares outstanding?

The 7,000 shares represent roughly 0.005% of the 152,674,214 shares outstanding.

Has the same insider sold Twilio shares recently?

Yes. The insider sold 12,056 shares on 31 Mar 2025 and 14,545 shares on 3 Apr 2025, generating $2.49 million combined gross proceeds.

Were the shares being sold acquired through open-market purchases or compensation?

All shares were obtained via restricted-stock lapses under equity compensation plans.