Datadog CFO trades: Options at $1.55, sells stock worth $1.95M

Rhea-AI Filing Summary

Datadog, Inc. (DDOG) Form 4 filing dated 06/23/2025 discloses CFO David M. Obstler’s latest insider transaction.

On 06/18/2025, Obstler exercised 15,000 stock options for Class B shares at an exercise price of $1.55, automatically converting them to an equal number of Class A shares. The option was fully vested and had no cash cost beyond the exercise price.

Immediately after conversion, he sold 15,000 Class A shares on the open market at $130.25 per share under a pre-arranged Rule 10b5-1 trading plan dated 06/12/2024, generating gross proceeds of roughly $1.95 million.

Following the sale, Obstler’s direct ownership stands at 399,270 Class A shares. In addition, a family trust holds 92,397 Class A shares for which he reports indirect beneficial ownership. The Class B to Class A conversion is consistent with Datadog’s dual-class structure that allows voluntary one-for-one conversion at any time.

No other derivative positions were opened or closed, and there is no indication of material company-level events in the filing. The transaction appears to be routine liquidity management rather than a strategic shift in ownership, given the executive’s remaining significant equity stake.

Positive

• Executive maintains substantial ownership of 399,270 Class A shares plus 92,397 held in a trust, suggesting continued alignment with shareholders.
• Transaction executed under a Rule 10b5-1 plan, enhancing transparency and reducing potential insider-information concerns.

Negative

• Net reduction of 15,000 Class A shares (≈$1.95 million) could be perceived as modest insider selling pressure.
• Sale price of $130.25 exceeds the low option strike, highlighting a large personal gain that may draw investor scrutiny despite being routine.

Insights

Financial Analyst

TL;DR: Routine 15k-share sale by CFO; sizable stake retained—neutral short-term signal.

The $1.55 option exercise followed by a same-day sale at $130.25 is a classic cash-less transaction, locking in ≈$1.95 million in pre-tax gains. Because the shares were sold under a 10b5-1 plan, the timing was pre-scheduled, reducing informational value. Obstler still controls about 399k shares directly (~$52 million at the sale price) plus 92k indirectly, so his net exposure remains high. For investors, the move signals personal diversification, not lack of confidence. Volume (15k) is only ~0.02 % of DDOG’s float and unlikely to impact liquidity or valuation.

Corporate Governance Expert

TL;DR: Pre-planned sale under 10b5-1 limits governance concerns; dual-class conversion mechanics normal.

The filing demonstrates proper Rule 10b5-1 usage, enhancing transparency amid heightened SEC scrutiny of executive trading plans. The one-for-one conversion from Class B to Class A is permitted by Datadog’s charter and does not alter voting control. No red flags emerge regarding insider information misuse or rapid share disposal. Governance impact is neutral.

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)
06/18/2025

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	06/18/2025		C(1)		15,000	A	$1.55	414,270	D
Class A Common Stock	06/18/2025		S(2)		15,000	D	$130.25	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	06/18/2025		M			15,000	(3)	09/06/2028	Class B Common Stock	15,000	$0	30,000	D
Class B Common Stock	(1)	06/18/2025		M		15,000		(1)	(1)	Class A Common Stock	15,000	$0	30,603	D
Class B Common Stock	(1)	06/18/2025		C(1)			15,000	(1)	(1)	Class A Common Stock	15,000	$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	06/23/2025
	** 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 (DDOG) shares did the CFO sell?

David Obstler sold 15,000 Class A shares on 06/18/2025.

At what price were the DDOG shares sold?

The shares were sold at $130.25 per share.

What was the exercise price of the options converted?

The options were exercised at $1.55 per share.

Does the CFO still own Datadog stock after the sale?

Yes. He holds 399,270 Class A shares directly and 92,397 additional shares indirectly through a trust.

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

Yes. The Form 4 states the sale was made under a 10b5-1 plan dated 06/12/2024.