Datadog trust plans $2.65M Class A share sale

A trust associated with Datadog’s CFO family filed a Rule 144 notice to sell 12,000 Class A shares, with recent related sales totaling 16,524 shares.

Rhea-AI Filing Summary

Datadog, Inc. (DDOG) received a Rule 144 notice for a planned sale of Class A Common Stock by the DAVID OBSTLER CHILDREN 2019 TRUST FBO ALISON OBSTLER. The trust plans to sell 12,000 Class A shares through Morgan Stanley Smith Barney LLC, with a stated aggregate value of $2,654,520.00, and the shares were acquired from previously exercised stock options.

The notice also reports that David Obstler sold 16,524 Class A shares during the past three months for aggregate proceeds of $3,518,027.35. The securities to be sold were acquired through RSUs/PSUs or option exercises and were registered on Form S-8.

Key Figures

Planned shares to be sold: 12,000 shares Aggregate value of planned sale: $2,654,520.00 Date of planned sale context: September 14, 2026 +5 more

8 metrics

Planned shares to be sold 12,000 shares Class A Common Stock to be sold under Rule 144 by the trust

Aggregate value of planned sale $2,654,520.00 Stated aggregate value for 12,000 Class A shares

Date of planned sale context September 14, 2026 Date associated with the planned sale and notice

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

Aggregate proceeds from past sale $3,518,027.35 Proceeds from 16,524 Class A shares sold in past 3 months

Security class Class A Common Stock Datadog, Inc. securities covered by the notice

Form type for registration Form S-8 Form on which the RSU/PSU or option shares were registered

Rule relied upon Rule 144 Provision under which the planned sale is being made

Key Terms

Rule 144, Form S-8, RSU, PSU, +2 more

6 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 financial

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

Restricted stock units (RSUs) are a form of company shares given to employees as part of their compensation, usually with certain restrictions or conditions, such as remaining with the company for a set period. When these restrictions lift, employees receive actual shares that they can sell or hold. For investors, RSUs can impact a company's stock supply and reflect the company's commitment to attracting and retaining talent.

PSU financial

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

A PSU is a company where the government owns a controlling stake and often plays a direct role in its management and strategy. Think of it like a business that operates with public oversight, similar to a town-run utility versus a private neighborhood service. Investors watch PSUs differently because government involvement can affect profits, dividend policies, regulatory treatment and stability, so these stocks may behave more like policy instruments than pure market-driven enterprises.

Previously Exercised Stock Options financial

"Previously Exercised Stock Options | Issuer"

Class A Common financial

"Class A Common | Morgan Stanley Smith Barney LLC Executive Financial Services"

FAQ

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

What share sale is being reported for Datadog, Inc. (DDOG) in this Form 144?

A trust named DAVID OBSTLER CHILDREN 2019 TRUST FBO ALISON OBSTLER filed to sell 12,000 Class A Common shares of Datadog, Inc. The sale is to be executed through Morgan Stanley Smith Barney LLC under Rule 144.

What is the approximate value of the Datadog (DDOG) shares the trust plans to sell?

The planned sale covers 12,000 Class A shares of Datadog, Inc. with an aggregate stated value of $2,654,520.00, according to the Rule 144 notice.

How were the Datadog (DDOG) shares to be sold by the trust acquired?

The notice states that the securities to be sold were acquired through RSU/PSU grants or upon option exercise and that these shares were registered on Form S-8.

What Datadog (DDOG) insider sales occurred in the past three months?

The filing reports that David Obstler sold 16,524 Class A Common shares of Datadog, Inc. on September 2, 2026 for aggregate proceeds of $3,518,027.35 during the past three months.

Which broker is handling the planned Datadog (DDOG) share sale under Rule 144?

The planned sale of 12,000 Class A shares for the trust will be handled by Morgan Stanley Smith Barney LLC Executive Financial Services at 1 New York Plaza, New York, as disclosed in the notice.

On what date was the Rule 144 notice for Datadog (DDOG) filed?

The Rule 144 notice for the proposed sale of Datadog, Inc. shares is dated September 14, 2026, as shown in the Date of Notice section.

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

Available on EDGAR 09/14/2026 - 05:11 PM Accepted by SEC EDGAR 09/14/2026 - 04:45 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 ALISON 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	03/05/2019	Previously Exercised Stock Options	Issuer			12000	03/05/2019	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)