DDOG Insider Cashes Out 20k Shares Worth $2.5M Under 10b5-1 Plan

Rhea-AI Filing Summary

Datadog (NASDAQ: DDOG) filed a Form 4 detailing CFO David M. Obstler’s insider transactions on 17 June 2025.

The filing shows he exercised 20,000 stock options at an exercise price of $1.55 (Class B converting to Class A) and immediately sold 20,000 Class A shares at an average price of $125.25 pursuant to a pre-arranged Rule 10b5-1 trading plan. Gross sale proceeds total roughly $2.5 million.

Following the transactions, Obstler’s direct Class A holdings decreased from 419,270 to 399,270 shares, while he continues to hold 92,397 shares indirectly through the Obstler Children 2019 Trust and retains additional derivative securities. No other equity classes were affected, and there were no new option grants.

Positive

• None.

Negative

• CFO David M. Obstler sold 20,000 Class A shares worth approximately $2.5 million, reducing his directly held stake by about 5%.

Insights

Portfolio Manager

TL;DR: $2.5 M sale trims CFO’s direct stake by ~5%, neutral-to-slightly negative signal.

The Form 4 reveals a modest but meaningful disposition: 20 k shares sold at $125.25, roughly 5 % of Obstler’s directly held position and above recent trading ranges. Although the sale is conducted under a 10b5-1 plan—mitigating concerns of opportunistic timing—the magnitude (>$2 M) and the fact that it equals the shares acquired via option exercise suggest a net cash-out rather than increased ownership. Insider sales of this size from a key financial executive can weigh on sentiment, particularly given Datadog’s premium valuation. However, Obstler maintains a sizable 399 k share stake plus 92 k indirect shares, indicating continued alignment. Overall impact: modestly negative but not thesis-changing.

Corporate Governance Expert

TL;DR: Pre-planned 10b5-1 trade reduces governance risk; impact largely neutral.

The disclosure specifies that the sale was executed under a June 12 2024 10b5-1 plan. Such plans provide an affirmative defense against insider-trading accusations and signal procedural compliance. The option exercised was fully vested, and conversion of Class B to Class A shares follows standard dual-class mechanics. Obstler’s remaining economic exposure (≈491 k shares combined direct and indirect) remains significant, mitigating concerns over diminished alignment. From a governance standpoint, frequency and transparency of Form 4 filings are consistent with best practices. Unless followed by additional large-scale disposals, the transaction should be viewed as routine liquidity management.

SEC Form 4

FORM 4

UNITED STATES SECURITIES AND EXCHANGE COMMISSION
Washington, D.C. 20549

STATEMENT OF CHANGES IN BENEFICIAL OWNERSHIP

Filed pursuant to Section 16(a) of the Securities Exchange Act of 1934
or Section 30(h) of the Investment Company Act of 1940

OMB APPROVAL

OMB Number:			3235-0287
Estimated average burden
hours per response:			0.5

Check this box if no longer subject to Section 16. Form 4 or Form 5 obligations may continue. See Instruction 1(b).

X

Check this box to indicate that a transaction was made pursuant to a contract, instruction or written plan for the purchase or sale of equity securities of the issuer that is intended to satisfy the affirmative defense conditions of Rule 10b5-1(c). See Instruction 10.

1. Name and Address of Reporting Person^*

OBSTLER DAVID M

(Last) (First) (Middle)

C/O DATADOG, INC.

620 8TH AVENUE, 45TH FLOOR

(Street)

NEW YORK NY 10018

(City) (State) (Zip)

2. Issuer Name and Ticker or Trading Symbol
Datadog, Inc. [ DDOG ]

5. Relationship of Reporting Person(s) to Issuer
(Check all applicable)

	Director		10% Owner
X	Officer (give title below)		Other (specify below)
	Chief Financial Officer

3. Date of Earliest Transaction (Month/Day/Year)
06/17/2025

4. If Amendment, Date of Original Filed (Month/Day/Year)

6. Individual or Joint/Group Filing (Check Applicable Line)

X	Form filed by One Reporting Person
	Form filed by More than One Reporting Person

Table I - Non-Derivative Securities Acquired, Disposed of, or Beneficially Owned
1. Title of Security (Instr. 3)	2. Transaction Date (Month/Day/Year)	2A. Deemed Execution Date, if any (Month/Day/Year)	3. Transaction Code (Instr. 8)		4. Securities Acquired (A) or Disposed Of (D) (Instr. 3, 4 and 5)			5. Amount of Securities Beneficially Owned Following Reported Transaction(s) (Instr. 3 and 4)	6. Ownership Form: Direct (D) or Indirect (I) (Instr. 4)	7. Nature of Indirect Beneficial Ownership (Instr. 4)
			Code	V	Amount	(A) or (D)	Price
Class A Common Stock	06/17/2025		C(1)		20,000	A	$1.55	419,270	D
Class A Common Stock	06/17/2025		S(2)		20,000	D	$125.25	399,270	D

Table II - Derivative Securities Acquired, Disposed of, or Beneficially Owned (e.g., puts, calls, warrants, options, convertible securities)
1. Title of Derivative Security (Instr. 3)	2. Conversion or Exercise Price of Derivative Security	3. Transaction Date (Month/Day/Year)	3A. Deemed Execution Date, if any (Month/Day/Year)	4. Transaction Code (Instr. 8)		5. Number of Derivative Securities Acquired (A) or Disposed of (D) (Instr. 3, 4 and 5)		6. Date Exercisable and Expiration Date (Month/Day/Year)		7. Title and Amount of Securities Underlying Derivative Security (Instr. 3 and 4)		8. Price of Derivative Security (Instr. 5)	9. Number of derivative Securities Beneficially Owned Following Reported Transaction(s) (Instr. 4)	10. Ownership Form: Direct (D) or Indirect (I) (Instr. 4)	11. Nature of Indirect Beneficial Ownership (Instr. 4)
				Code	V	(A)	(D)	Date Exercisable	Expiration Date	Title	Amount or Number of Shares
Stock Option (Right to Buy)	$1.55	06/17/2025		M			20,000	(3)	09/06/2028	Class B Common Stock	20,000	$0	45,000	D
Class B Common Stock	(1)	06/17/2025		M		20,000		(1)	(1)	Class A Common Stock	20,000	$0	35,603	D
Class B Common Stock	(1)	06/17/2025		C(1)			20,000	(1)	(1)	Class A Common Stock	20,000	$0	15,603	D
Class B Common Stock	(1)							(1)	(1)	Class A Common Stock	92,397		92,397	I	By Trust(4)

Explanation of Responses:

1. Each share of Class B Common Stock is convertible at any time at the option of the Reporting Person into one share of Class A Common Stock and has no expiration date. Each share of Class B Common Stock will convert automatically into one share of Class A Common Stock upon the earliest of: (i) any transfer, whether or not for value, except for certain "Permitted Transfers" as defined in the Issuer's amended and restated certificate of incorporation, (ii) the death of the Reporting Person in the case of shares held directly or in a trustee capacity, and (iii) the tenth anniversary of the Issuer's initial public offering of its Class A Common Stock.

2. Shares sold pursuant to a 10b5-1 plan dated June 12, 2024.

3. Option is fully vested and exercisable.

4. Shares are held directly by the Obstler Children 2019 Trust, of which the Reporting Person's spouse is Trustee.

Remarks:

	/s/ Kerry Acocella, Attorney-in-Fact	06/18/2025
	** Signature of Reporting Person	Date
Reminder: Report on a separate line for each class of securities beneficially owned directly or indirectly.
* If the form is filed by more than one reporting person, see Instruction 4 (b)(v).
** Intentional misstatements or omissions of facts constitute Federal Criminal Violations See 18 U.S.C. 1001 and 15 U.S.C. 78ff(a).
Note: File three copies of this Form, one of which must be manually signed. If space is insufficient, see Instruction 6 for procedure.
Persons who respond to the collection of information contained in this form are not required to respond unless the form displays a currently valid OMB Number.

FAQ

How many Datadog shares did CFO David M. Obstler sell on 17 June 2025?

He sold 20,000 Class A shares according to the Form 4.

At what price were the shares sold by DDOG’s CFO?

The shares were sold at an average price of $125.25 per share.

Did the CFO exercise options before selling the shares?

Yes. He exercised 20,000 options with a $1.55 strike price and converted Class B to Class A shares prior to the sale.

How many Datadog shares does the CFO own after the transaction?

He directly owns 399,270 Class A shares and indirectly holds 92,397 shares via a family trust.

Was the sale executed under a 10b5-1 trading plan?

Yes, the filing states the sale was made pursuant to a Rule 10b5-1 plan dated 12 June 2024.