Datadog CFO sells 10,000 shares at $241.25
Two trusts for Obstler's children converted Class B shares into Class A before the trusts' sales.
Rhea-AI Filing Summary
Datadog, Inc. Chief Financial Officer David M. Obstler sold 10,000 Class A shares directly at $241.25 per share on September 21, 2026; his direct Class A holdings afterward were 368,067 shares. The Obstler Children 2019 Trust FBO his child and the Obstler Children 2019 Trust FBO his other child each converted 3,000 Class B shares into Class A and sold 3,000 Class A shares at $241.25 per share; his spouse is trustee of both. Each sale was under a 10b5-1 plan dated June 13, 2026. As of September 21, 2026, he also reported 8,103 directly held Class B shares, each convertible into one Class A share.
Positive
- None.
Negative
- None.
Insights
Analyzing...
Insider Trade Summary 10b5-1
Exercise and sale activity reported; no spread calculated
Exercise and Sale
8 txns
Insider
OBSTLER DAVID M
Role
Chief Financial Officer
Sold
16,000 shs ($3.86M)
Approx. gross sale proceeds
$3.86M
| Type | Security | Shares | Price | Value |
|---|---|---|---|---|
| Conversion | Class B Common Stock F2, F3 | 3,000 | $0.00 | $0.00 |
| Conversion | Class B Common Stock F2, F4 | 3,000 | $0.00 | $0.00 |
| Sale | Class A Common Stock F1 | 10,000 | $241.25 | $2.41M |
| Conversion | Class A Common Stock F2, F3 | 3,000 | $0.00 | $0.00 |
| Sale | Class A Common Stock F1, F3 | 3,000 | $241.25 | $724K |
| Conversion | Class A Common Stock F2, F4 | 3,000 | $0.00 | $0.00 |
| Sale | Class A Common Stock F1, F4 | 3,000 | $241.25 | $724K |
| holding | Class B Common Stock F2 | -- | -- | -- |
Holdings After Transaction:
Class B Common Stock — 62,397 contracts (Indirect, By Trust);
Class A Common Stock — 368,067 shares (Direct);
Class A Common Stock — 0 shares (Indirect, By Trust);
Class B Common Stock — 8,103 contracts (Direct)
Footnotes (4)
- F1. Shares sold pursuant to a 10b5-1 plan dated June 13, 2026.
- F2. 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.
- F3. Shares are held directly by Obstler Children 2019 Trust FBO the Reporting Person's other child, of which the Reporting Person's spouse is Trustee. See Footnote 4.
- F4. Shares are held directly by Obstler Children 2019 Trust FBO the Reporting Person's child, of which the Reporting Person's spouse is Trustee. Obstler Children 2019 Trust FBO the Reporting Person's child and Obstler Children 2019 Trust FBO the Reporting Person's other child are separate trusts for the benefit of the Reporting Person's children with substantially identical terms.
Key Figures
Class A shares sold directly: 10,000 shares
Sale price: $241.25 per share
Direct Class A shares following sale: 368,067 shares
+3 more
6 metrics
Class A shares sold directly
10,000 shares
By David M. Obstler on September 21, 2026
Sale price
$241.25 per share
Class A shares sold on September 21, 2026
Direct Class A shares following sale
368,067 shares
Reported after the September 21, 2026 sale
Class A shares sold by the trust for Obstler's child
3,000 shares
Obstler Children 2019 Trust FBO David M. Obstler's child; September 21, 2026
Class A shares sold by the trust for Obstler's other child
3,000 shares
Obstler Children 2019 Trust FBO David M. Obstler's other child; September 21, 2026
Directly held Class B shares
8,103 shares
Reported as of September 21, 2026; each convertible into one Class A share
Key Terms
10b5-1 plan, Permitted Transfers, Class B Common Stock, convert automatically
4 terms
10b5-1 plan regulatory
"Shares sold pursuant to a 10b5-1 plan dated June 13, 2026."
A 10b5-1 plan is a pre-arranged strategy that allows company insiders to buy or sell their shares at predetermined times and prices, even while they are aware of confidential information. It acts like a scheduled appointment for trading, helping ensure transactions happen transparently and legally, which can reassure investors that trades are not based on insider knowledge.
Permitted Transfers technical
"except for certain "Permitted Transfers""
Class B Common Stock financial
"Each share of Class B Common Stock is convertible"
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.
convert automatically technical
"will convert automatically into one share of Class A Common Stock"
FAQ
AI-generated questions and answers. How Rhea-AI works. Not financial advice.
How does DDOG Class B stock convert to Class A?
Each Class B share is convertible at any time, at the Reporting Person's option, into one Class A share. It also converts automatically upon the earliest of a transfer other than certain “Permitted Transfers,” the Reporting Person's death for shares held directly or in a trustee capacity, or the tenth anniversary of Datadog's initial public offering of Class A Common Stock.
AI-generated analysis. How Rhea-AI works. Not financial advice.
