Datadog trust plans $2.65M sale of 12,000 shares

Trust associated with Datadog’s CFO family filed to sell 12,000 DDOG Class A shares under Rule 144, following earlier insider share sales.

Rhea-AI Filing Summary

Datadog, Inc. (DDOG) received a Rule 144 notice for a planned sale of up to 12,000 shares of Class A common stock for the account of the DAVID OBSTLER CHILDREN 2019 TRUST FBO ANDREW OBSTLER. The shares are to be sold through Morgan Stanley Smith Barney LLC, with an indicated aggregate market value of $2,654,520.00 and reference to 334,904,614 Class A shares as a comparative figure as of the notice. The securities to be sold were acquired through RSUs, PSUs or option exercises and were registered on Form S-8. In the prior three months, a related party, David Obstler, sold 16,524 Class A shares for $3,518,027.35. The notice is dated September 14, 2026.

Key Figures

Shares to be sold: 12,000 shares of Class A common stock Aggregate market value of shares to be sold: $2,654,520.00 Reference share figure: 334,904,614 shares +3 more

6 metrics

Shares to be sold 12,000 shares of Class A common stock Planned Rule 144 sale for the trust’s account

Aggregate market value of shares to be sold $2,654,520.00 Indicated value for the 12,000 Class A shares in the planned sale

Reference share figure 334,904,614 shares Comparative Class A share figure cited alongside the Form 144 sale

Shares sold in prior 3 months 16,524 shares Class A shares sold by David Obstler on September 2, 2026

Aggregate value of prior sale $3,518,027.35 Value of 16,524 Class A shares sold on September 2, 2026

Date of notice September 14, 2026 Date the Form 144 notice was signed and submitted

Key Terms

Rule 144, Form S-8, RSU/PSU, Stock Options

4 terms

Rule 144 regulatory

"See the definition of "person" in 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.

Form S-8 regulatory

"were registered on Form S-8."

A Form S-8 is a U.S. Securities and Exchange Commission registration that lets a public company set aside shares for employee benefit plans and stock-based compensation. Think of it as opening a dedicated account that authorizes the company to issue or reserve stock for workers and directors; it matters to investors because it enables share dilution when those awards are granted or exercised and signals how management is compensated and incentivized.

RSU/PSU financial

"Securities to be sold, acquired through RSU/PSU or upon option exercise"

Stock Options financial

"Previously Exercised Stock Options"

Stock options are agreements that give a person the right to buy or sell a company's stock at a specific price within a certain time frame. They are often used as a reward or incentive, similar to a coupon that can be used later if the stock price rises, allowing the holder to make a profit.

FAQ

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

What does the Form 144 filing disclose for Datadog (DDOG)?

It discloses that the DAVID OBSTLER CHILDREN 2019 TRUST FBO ANDREW OBSTLER plans to sell 12,000 shares of Datadog Class A common stock under Rule 144, with an indicated aggregate market value of $2,654,520.00, using Morgan Stanley Smith Barney LLC as broker.

How many Datadog (DDOG) shares are being proposed for sale in this notice?

The notice covers a proposed sale of 12,000 shares of Datadog Class A common stock for the trust’s account, with an indicated aggregate market value of $2,654,520.00 as of the filing details.

What prior Datadog (DDOG) share sales are referenced in the last three months?

The filing notes that David Obstler sold 16,524 Datadog Class A shares on September 2, 2026, for a total of $3,518,027.35, which must be aggregated with the trust’s planned sales under Rule 144.

How were the Datadog (DDOG) shares in this Form 144 acquired?

The remarks state that the securities to be sold were acquired through RSUs, PSUs or upon option exercise and that these awards were registered on Form S-8.

When is the planned sale date for the Datadog (DDOG) shares under this Form 144?

The proposed transaction details list a date of September 14, 2026 in connection with the sale of 12,000 Datadog Class A common shares under Rule 144.

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

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Available on EDGAR 09/14/2026 - 05:11 PM Accepted by SEC EDGAR 09/14/2026 - 04:46 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	0001120741
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	Datadog, Inc.
SEC File Number	001-39051
Address of Issuer	620 8th Avenue, 45th Floor New York NEW YORK 10018
Phone	8663294466
Name of Person for Whose Account the Securities are To Be Sold	DAVID OBSTLER CHILDREN 2019 TRUST FBO ANDREW OBSTLER
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

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 Common	Morgan Stanley Smith Barney LLC Executive Financial Services 1 New York Plaza 8th Floor New York NY 10004	12000	2654520.00	334904614	09/14/2026	NASDAQ

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 Common	03/15/2019	Previously Exercised Stock Options	Issuer			12000	03/15/2019	Cash

* 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
DAVID OBSTLER 620 8th Avenue, 45th Floor New York NY 10018	Class A Common	09/02/2026	16524	3518027.35

144: Remarks and Signature

Remarks	Securities to be sold, acquired through RSU/PSU or upon option exercise, were registered on Form S-8.
Date of Notice	09/14/2026
Date of Plan Adoption or Giving of Instruction, If Relying on Rule 10b5-1	06/13/2026
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	/s/ Thea Obstler
ATTENTION: Intentional misstatements or omission of facts constitute Federal Criminal Violations (See 18 U.S.C. 1001)