DDOG Insider David Obstler Files Form 144 for 15,000-Share Sale

Rhea-AI Filing Summary

This Form 144 filing indicates that a Datadog, Inc. (DDOG) insider – identified in the filing’s sales history as David Obstler – intends to sell 15,000 shares of Class A common stock through Morgan Stanley Smith Barney on or about 18 June 2025. At the filing’s stated market price, the planned sale is valued at $1.87 million.

The filing also discloses that the same insider sold an aggregate 75,016 shares over the last three months under Rule 10b5-1 trading plans, realising approximately $9.0 million in gross proceeds. Combined with the proposed sale, total disposals reach roughly 90,016 shares. Relative to Datadog’s reported 319.5 million Class A shares outstanding, the new transaction represents about 0.005 % of shares and is therefore immaterial to share count and voting power.

Rule 144 and 10b5-1 frameworks signal that the trades were pre-scheduled, mitigating concerns about the insider acting on non-public information. Nonetheless, continued selling by the company’s long-time Chief Financial Officer may be viewed as a modestly negative sentiment indicator by some investors, although the absolute size remains small.

Positive

• Use of Rule 10b5-1 trading plan demonstrates adherence to best-practice insider-trading safeguards, reducing information-asymmetry risk.

Negative

• Continued selling by the CFO may be interpreted as a lack of confidence or a desire to diversify, creating mildly negative investor sentiment despite small size.

Insights

Securities Analyst

TL;DR – Small, pre-planned CFO sale; negligible dilution, mildly negative sentiment.

The filing is routine. The additional 15 k shares equate to less than 0.01 % of outstanding stock and follow 75 k shares already sold under Rule 10b5-1. Because the plans were pre-established, the risk of trading on undisclosed information is low. Financially, the transaction has no impact on Datadog’s capital structure or cash flows; it is simply a secondary sale. That said, serial insider selling by the CFO can feed bearish narratives, particularly when clustered over a short period. I classify the market impact as not impactful and sentiment as slightly negative but well within normal executive diversification behaviour.

Corporate Governance Expert

TL;DR – Governance-neutral, transparency maintained via Rule 144 and 10b5-1.

From a governance lens, the key factor is compliance. The insider is adhering to Rule 144 notice requirements and leveraging a 10b5-1 plan, providing audit-ready documentation that trades are non-opportunistic. No red flags such as option backdating, accelerated vesting, or concentrated disposals appear. The volume remains far below the rule’s volume limitations (1 % of outstanding shares or average weekly volume). Therefore, the filing is procedurally sound and unlikely to trigger governance concerns. Impact on shareholder rights and control is effectively nil.

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

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	15000	1872600.00	319498060	06/18/2025	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	06/18/2025	Exercise of Stock Options	Issuer			15000	06/18/2025	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 New York NY 10018	Class A Common	06/17/2025	20000	2505000.00
10b5-1 Sales for DAVID OBSTLER 620 8th Avenue New York NY 10018	Class A Common	06/04/2025	20000	2405000.00
DAVID OBSTLER 620 8th Avenue New York NY 10018	Class A Common	06/02/2025	12516	1462381.96
10b5-1 Sales for DAVID OBSTLER 620 8th Avenue New York NY 10018	Class A Common	06/02/2025	22500	2648666.25

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 Datadog (DDOG) shares is the insider proposing to sell?

The notice covers 15,000 Class A shares.

What is the estimated dollar value of the planned DDOG sale?

At the stated market price, the sale is worth approximately $1.87 million.

Who is the selling insider in this Form 144 filing?

Sales history in the filing identifies David Obstler, Datadog’s CFO, as the seller.

How significant is the sale relative to Datadog’s share count?

The 15,000 shares equal roughly 0.005 % of the company’s 319.5 million outstanding Class A shares.

Were there prior insider sales disclosed?

Yes. Over the past three months, the same insider sold 75,016 shares for about $9.0 million in gross proceeds.

Does this filing raise governance concerns?

The trade is pre-scheduled under Rule 10b5-1 and complies with Rule 144, so no governance red flags are evident.