Datadog officer plans $3.8M share sale under Rule 144

Datadog officer David Obstler has filed a Rule 144 notice covering 16,030 Class A shares, with prior sizable sales also reported.

Rhea-AI Filing Summary

Datadog, Inc. (DDOG) has a Rule 144 notice filed for planned sales of its Class A common stock by David Obstler, identified as an officer. The notice covers 16,030 shares, with an indicated aggregate market value of $3,767,050, alongside disclosure of prior sales in the past three months.

Key Figures

Shares to be sold: 16,030 shares Aggregate market value of planned sale: $3,767,050 Shares outstanding: 334,904,614 shares +4 more

7 metrics

Shares to be sold 16,030 shares Planned sale of Datadog Class A common stock under Rule 144

Aggregate market value of planned sale $3,767,050 Indicated value for the 16,030 shares covered by the notice

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

Recent sale June 8, 2026 75,000 shares for $17,376,592.50 Past three months sales by David Obstler

Recent sale June 2, 2026 16,323 shares for $4,360,761.27 Past three months sales by David Obstler

Vesting date September 1, 2026 Restricted Stock Units and Performance Stock Units vesting tied to planned sale

Date of notice September 2, 2026 Date associated with the Rule 144 notice filing

Key Terms

Rule 144, Restricted Stock Units, Performance Stock Units, Form S-8

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.

Restricted Stock Units financial

"Restricted Stock Units and Performance Stock Units vesting"

Restricted stock units are a type of company reward where employees are promised shares of stock, but they only fully own these shares after meeting certain conditions, like staying with the company for a set time. They matter because they can become valuable assets and are often used to motivate employees to help the company succeed.

Performance Stock Units financial

"Restricted Stock Units and Performance Stock Units vesting"

Performance stock units are a type of company award that grants employees shares of stock only if certain performance goals are met. They motivate employees to work toward specific company achievements, aligning their interests with those of shareholders. For investors, they can influence a company's future stock supply and reflect management’s confidence in reaching key targets.

Form S-8 regulatory

"Securities to be sold 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.

FAQ

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

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

The notice discloses that David Obstler, an officer of Datadog, intends to sell 16,030 shares of Class A common stock under Rule 144, with an indicated aggregate market value of $3,767,050, and lists his related sales in the prior three months.

How many Datadog (DDOG) shares are covered by this Rule 144 notice?

The Rule 144 notice covers the proposed sale of 16,030 shares of Datadog Class A common stock, related to Restricted Stock Units and Performance Stock Units vesting on September 1, 2026.

What were David Obstler’s recent sales of Datadog (DDOG) stock?

In the past three months, David Obstler sold 75,000 shares of Class A common stock on June 8, 2026 for $17,376,592.50 and 16,323 shares on June 2, 2026 for $4,360,761.27.

What is the market value and share count context for this Datadog (DDOG) sale?

The proposed 16,030-share sale has an indicated aggregate market value of $3,767,050. Datadog had 334,904,614 shares of Class A common stock outstanding as of the notice, providing context for the relative size of the planned sale.

How are the Datadog (DDOG) shares in this Form 144 related to compensation?

The 16,030 shares to be sold are tied to Restricted Stock Units and Performance Stock Units vesting on September 1, 2026, with the transaction described as involving the issuer and categorized as compensation.

On which exchange are the Datadog (DDOG) shares in this notice listed?

The Class A common stock covered by the notice is listed on the NASDAQ, as referenced in connection with the 16,030 shares and the indicated aggregate market value of $3,767,050.

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

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Available on EDGAR 09/02/2026 - 04:34 PM EDT Accepted by SEC EDGAR 09/02/2026 - 04:33 PM EDT 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	866-329-4466
Name of Person for Whose Account the Securities are To Be Sold	David 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 Stock	Morgan Stanley Smith Barney LLC Executive Services 200 W Civic Center Dr - 4th Floor Sandy UT 84070	16030	3767050	334904614	09/02/2026	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 Stock	09/01/2026	Restricted Stock Units and Performance Stock Units vesting	Issuer			16030	09/01/2026	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
David Obstler 620 8th Avenue, 45th floor New York NY 10018	Class A Common Stock	06/08/2026	75000	17376592.5
David Obstler 620 8th Avenue, 45th floor New York NY 10018	Class A Common Stock	06/02/2026	16323	4360761.27

144: Remarks and Signature

Remarks	Securities to be sold were registered on Form S-8
Date of Notice	09/02/2026
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/ David Obstler
ATTENTION: Intentional misstatements or omission of facts constitute Federal Criminal Violations (See 18 U.S.C. 1001)