Datadog trust plans $689K Rule 144 share sale

Trust accounts related to a Datadog executive have filed to sell Class A shares under Rule 144, alongside recent 10b5-1 plan sales.

Rhea-AI Filing Summary

Datadog, Inc. (DDOG) has a notice of proposed sale under Rule 144 filed for Class A common stock held by the David Obstler Children 2019 Trust FBO Andrew Obstler. The trust plans to sell 3,000 Class A shares through Morgan Stanley Smith Barney LLC, with an aggregate market value of $689,760.00 as of the notice, and Datadog reports 334,904,614 Class A shares outstanding. The shares to be sold were acquired from previously exercised stock options on March 5, 2019 and were registered on Form S-8. The notice also lists recent 10b5-1 plan sales of Datadog Class A shares during the past three months by David Obstler and related children’s trusts.

Key Figures

Planned shares to be sold: 3,000 shares Aggregate market value of planned sale: $689,760.00 Shares outstanding: 334,904,614 shares +5 more

8 metrics

Planned shares to be sold 3,000 shares Class A common stock by David Obstler Children 2019 Trust FBO Andrew Obstler

Aggregate market value of planned sale $689,760.00 Proposed Rule 144 sale of 3,000 Class A shares

Shares outstanding 334,904,614 shares Datadog Class A common stock outstanding as referenced in the notice

Sale date reference September 21, 2026 Date tied to the proposed Rule 144 sale entry

Past 10b5-1 sale by David Obstler 40,000 shares for $9,098,879.00 Class A common stock sale on September 14, 2026

Past 10b5-1 sale by each children’s trust 12,000 shares for $2,729,663.70 Each of two children’s trusts on September 14, 2026

Additional sale by David Obstler 16,524 shares for $3,518,027.35 Class A common stock sale on September 2, 2026

Acquisition date of shares to be sold March 5, 2019 Shares obtained from previously exercised stock options

Key Terms

Rule 144, 10b5-1, Form S-8, Previously Exercised Stock Options, +1 more

5 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.

10b5-1 regulatory

"10b5-1 Sales for DAVID OBSTLER 620 8th Avenue, 45th Floor"

A 10b5-1 plan is a pre-set schedule that lets company insiders buy or sell shares according to written instructions made when they do not possess material, nonpublic information. Think of it as a timed automatic payment for stock trades: it helps insiders avoid accusations of trading on secret information and gives outside investors a clearer signal about whether sales are routine or potentially informative about the company’s prospects.

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.

Previously Exercised Stock Options financial

"Previously Exercised Stock Options | Issuer"

RSU/PSU financial

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

FAQ

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

What does the Datadog (DDOG) Form 144 filing disclose about upcoming sales?

The filing discloses that the David Obstler Children 2019 Trust FBO Andrew Obstler intends to sell 3,000 Class A common shares of Datadog through Morgan Stanley Smith Barney LLC under Rule 144, with an indicated aggregate market value of $689,760.00.

Who is the selling security holder in this Datadog (DDOG) Form 144?

The selling security holder is the David Obstler Children 2019 Trust FBO Andrew Obstler. The form notes that information must also cover other persons whose sales are aggregated under Rule 144 paragraph (e).

How many Datadog (DDOG) shares were previously sold in the past three months?

The notice lists past three-month sales including 40,000 shares and 16,524 shares by David Obstler, and 12,000 shares each by two children’s trusts, all in Datadog Class A common stock, with disclosed dollar proceeds for each sale group.

Were the Datadog (DDOG) shares being sold under Rule 144 registered previously?

Yes. The remarks state that the securities to be sold, acquired through RSU/PSU or upon option exercise, were registered on Form S-8, indicating they originated from equity compensation plans.

What is the origin of the Datadog (DDOG) shares to be sold by the trust?

The 3,000 Class A shares to be sold by the David Obstler Children 2019 Trust FBO Andrew Obstler were acquired on March 5, 2019 from previously exercised stock options, with the issuer listed as Datadog, Inc.

Does the Datadog (DDOG) Form 144 mention trading plans?

Yes. The section on securities sold during the past three months identifies 10b5-1 sales for David Obstler and for two children’s trusts, all involving Class A common stock transactions on September 14, 2026.

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

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Available on EDGAR 09/21/2026 - 04:36 PM Accepted by SEC EDGAR 09/21/2026 - 04:35 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	3000	689760.00	334904614	09/21/2026	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 *
Common	03/05/2019	Previously Exercised Stock Options	Issuer			3000	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
10b5-1 Sales for DAVID OBSTLER 620 8th Avenue, 45th Floor New York NY 10018	Class A Common	09/14/2026	40000	9098879.00
10b5-1 Sales for DAVID OBSTLER CHILDREN 2019 TRUST FBO ALISON OBSTLER 620 8th Avenue, 45th Floor New York NY 10018	Class A Common	09/14/2026	12000	2729663.70
10b5-1 Sales for DAVID OBSTLER CHILDREN 2019 TRUST FBO ANDREW OBSTLER 620 8th Avenue, 45th Floor New York NY 10018	Class A Common	09/14/2026	12000	2729663.70
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	09/21/2026
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)