Datadog, Inc. (NASDAQ: DDOG) CFO sells 20,000 shares, retains 399,270 Class A

Rhea-AI Filing Summary

Datadog, Inc. reports that Chief Financial Officer David M. Obstler exercised fully vested stock options to acquire 20,000 shares at $1.55 per share, converted them into Class A Common Stock, and sold those 20,000 shares at $125.25 per share pursuant to a Rule 10b5-1 plan dated June 12, 2024.

After these transactions, he holds 399,270 Class A and 15,603 Class B shares directly, and 92,397 Class B shares indirectly through the Obstler Children 2019 Trust, with each Class B share convertible into one Class A share and having no expiration date.

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.

Insider Trade Summary

Exercise and sale activity reported; no spread calculated

Exercise and Sale 6 txns

Insider OBSTLER DAVID M

Role Chief Financial Officer

Sold 20,000 shs ($2.50M)

Approx. gross sale proceeds $2.50M

Approx. exercise cost $31K

Type	Security	Shares	Price	Value
Exercise	Stock Option (Right to Buy)	20,000	$0.00	$0.00
Exercise	Class B Common Stock	20,000	$0.00	$0.00
Conversion	Class B Common Stock	20,000	$0.00	$0.00
Conversion	Class A Common Stock	20,000	$1.55	$31K
Sale	Class A Common Stock	20,000	$125.25	$2.50M
holding	Class B Common Stock	--	--	--

Holdings After Transaction: Stock Option (Right to Buy) — 45,000 shares (Direct); Class B Common Stock — 15,603 shares (Direct); Class A Common Stock — 399,270 shares (Direct); Class B Common Stock — 92,397 shares (Indirect, By Trust)

Footnotes (4)

1. F1. 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. F2. Shares sold pursuant to a 10b5-1 plan dated June 12, 2024.
3. F3. Option is fully vested and exercisable.
4. F4. Shares are held directly by the Obstler Children 2019 Trust, of which the Reporting Person's spouse is Trustee.

Key Figures

Shares sold: 20,000 shares Sale price: $125.25 per share Option exercise price: $1.55 per share +3 more

6 metrics

Shares sold 20,000 shares Class A Common Stock sale on 2025-06-17 at $125.25 per share

Sale price $125.25 per share Non-derivative sale of 20,000 Class A shares

Option exercise price $1.55 per share Stock option (Right to Buy) exercised for 20,000 underlying shares

Direct Class A holding 399,270 shares Post-transaction Class A Common Stock directly owned by CFO

Direct Class B holding 15,603 shares Post-transaction Class B Common Stock directly owned by CFO

Indirect Class B holding 92,397 shares Class B shares held indirectly via Obstler Children 2019 Trust

Key Terms

Rule 10b5-1 plan, Class B Common Stock, Permitted Transfers, amended and restated certificate of incorporation

4 terms

Rule 10b5-1 plan financial

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

A Rule 10b5-1 plan is a prearranged, written schedule that lets corporate insiders buy or sell company stock at set times or amounts, even if they later learn material nonpublic information. Think of it like setting an automatic thermostat for trades: it creates a clear record that trades were planned in advance, reducing the risk of insider-trading accusations and helping investors trust that insider transactions are routine rather than based on secret information.

Class B Common Stock financial

"Each share of Class B Common Stock is convertible at any time at the option of the Reporting Person."

A class B common stock is one of multiple types of a company’s ordinary shares that carries specific rights—often different voting power or dividend priority—compared with other classes. For investors it matters because those differences affect how much influence you have over company decisions, the income you might receive, and how freely the shares trade; think of it like owning a car with different keys: some keys let you start the engine and open the trunk, others only unlock the door.

Permitted Transfers regulatory

"except for certain Permitted Transfers as defined in the issuer's amended and restated certificate of incorporation."

amended and restated certificate of incorporation regulatory

"Permitted Transfers as defined in the issuer's amended and restated certificate of incorporation."

A company’s amended and restated certificate of incorporation is an updated version of its foundational legal charter that replaces the older document and folds in all changes into one clear copy; it spells out corporate structure, classes of stock, shareholder rights and key governance rules. Investors care because it can change who controls the company, how votes are counted, what claims shareholders have on assets or dividends, and can introduce or remove protections against takeovers—like updating a house title after a major renovation to show who owns what and under what rules.

FAQ

What did Datadog (DDOG) CFO David M. Obstler do in this Form 4?

He exercised options for 20,000 shares at $1.55 and sold 20,000 Class A shares at $125.25. Afterward, he held 399,270 Class A and 15,603 Class B shares directly, plus 92,397 Class B shares indirectly via a family trust.

How many Datadog (DDOG) shares did the CFO sell and at what price?

David M. Obstler sold 20,000 shares of Class A Common Stock at a price of $125.25 per share. These shares were received following an option exercise and subsequent conversions reported on the same date.

What are David Obstler’s Datadog (DDOG) holdings after these transactions?

Following the reported trades, he directly holds 399,270 Class A and 15,603 Class B shares. In addition, a family trust associated with him holds 92,397 Class B shares, which are convertible into Class A Common Stock.

Were the Datadog (DDOG) share sales made under a Rule 10b5-1 plan?

A footnote states the shares sold were pursuant to a Rule 10b5-1 plan dated June 12, 2024. Such plans are pre-arranged trading programs intended to allow insiders to sell shares according to predetermined terms.

What option exercise did the Datadog (DDOG) CFO report?

He exercised a fully vested stock option covering 20,000 shares at an exercise price of $1.55 per share. The exercise resulted in Class B shares that were then converted into Class A shares before being sold.

How are Datadog (DDOG) Class B shares held by the CFO treated?

Each Class B Common Share is convertible into one Class A share and has no expiration date. Automatic conversion can occur upon certain transfers, the reporting person’s death, or the tenth anniversary of Datadog’s initial public offering.

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

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Form 4 Insider Transactions: What Each Field Means →

Accepted by SEC EDGAR 06/18/2025 - 04:52 PM Learn about SEC filing dates

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.