Datadog CFO trusts sell 24,000 shares in plan trade
Datadog, Inc. (DDOG) reports that Chief Financial Officer David M. Obstler had trusts associated with his family convert and sell shares on September 14, 2026.
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Form Type
4
Rhea-AI Filing Summary
Datadog, Inc. (DDOG) reports that Chief Financial Officer David M. Obstler had trusts associated with his family convert and sell shares on September 14, 2026. Trusts converted 24,000 Class B shares into 24,000 Class A shares and sold 24,000 Class A shares in multiple trades under a Rule 10b5-1 plan. Obstler continues to hold 8,103 Class B shares directly, each convertible into one Class A share.
Insider Trade Summary 10b5-1
Exercise and sale activity reported; no spread calculated
Exercise and Sale
30 txns
Insider
OBSTLER DAVID M
Role
Chief Financial Officer
Sold
24,000 shs ($5.46M)
Approx. gross sale proceeds
$5.46M
Share of Position Sold
100%
| Type | Security | Shares | Price | Value |
|---|---|---|---|---|
| Conversion | Class B Common Stock F1, F2 | 12,000 | $0.00 | $0.00 |
| Conversion | Class B Common Stock F1, F17 | 12,000 | $0.00 | $0.00 |
| Conversion | Class A Common Stock F1, F2 | 12,000 | $0.00 | $0.00 |
| Sale | Class A Common Stock F3, F4, F2 | 798 | $221.2365 | $177K |
| Sale | Class A Common Stock F3, F5, F2 | 1,624 | $222.1661 | $361K |
| Sale | Class A Common Stock F3, F6, F2 | 738 | $223.1165 | $165K |
| Sale | Class A Common Stock F3, F7, F2 | 545 | $224.3433 | $122K |
| Sale | Class A Common Stock F3, F8, F2 | 1,182 | $225.1332 | $266K |
| Sale | Class A Common Stock F3, F9, F2 | 190 | $226.1915 | $43K |
| Sale | Class A Common Stock F3, F10, F2 | 169 | $227.7159 | $38K |
| Sale | Class A Common Stock F3, F11, F2 | 360 | $228.5859 | $82K |
| Sale | Class A Common Stock F3, F12, F2 | 2,873 | $229.9209 | $661K |
| Sale | Class A Common Stock F3, F13, F2 | 1,689 | $230.5094 | $389K |
| Sale | Class A Common Stock F3, F14, F2 | 724 | $231.5317 | $168K |
| Sale | Class A Common Stock F3, F15, F2 | 918 | $232.7079 | $214K |
| Sale | Class A Common Stock F3, F16, F2 | 190 | $233.2997 | $44K |
| Conversion | Class A Common Stock F1, F17 | 12,000 | $0.00 | $0.00 |
| Sale | Class A Common Stock F3, F4, F17 | 786 | $221.2389 | $174K |
| Sale | Class A Common Stock F3, F5, F17 | 1,635 | $222.1623 | $363K |
| Sale | Class A Common Stock F3, F6, F17 | 725 | $223.1157 | $162K |
| Sale | Class A Common Stock F3, F7, F17 | 525 | $224.3448 | $118K |
| Sale | Class A Common Stock F3, F8, F17 | 1,169 | $225.1313 | $263K |
| Sale | Class A Common Stock F3, F9, F17 | 181 | $226.1915 | $41K |
| Sale | Class A Common Stock F3, F10, F17 | 163 | $227.7183 | $37K |
| Sale | Class A Common Stock F3, F11, F17 | 358 | $228.5972 | $82K |
| Sale | Class A Common Stock F3, F12, F17 | 2,935 | $229.9168 | $675K |
| Sale | Class A Common Stock F3, F18, F17 | 1,729 | $230.5063 | $399K |
| Sale | Class A Common Stock F3, F14, F17 | 713 | $231.5314 | $165K |
| Sale | Class A Common Stock F3, F15, F17 | 899 | $232.7071 | $209K |
| Sale | Class A Common Stock F3, F16, F17 | 182 | $233.2996 | $42K |
| Holding | Class B Common Stock F1 | -- | -- | -- |
Holdings After Transaction:
Class B Common Stock — 68,397 contracts (Indirect, By Trust);
Class A Common Stock — 0 shares (Indirect, By Trust);
Class B Common Stock — 8,103 contracts (Direct)
Holdings Before and After:
Class B Common Stock, 92,397 to 68,397 contracts (Indirect, By Trust);
Class A Common Stock, 0 to 0 shares (Indirect, By Trust)
Other Insiders: 8 other insiders reported open-market sales of this stock in the 30 days up to this filing.
Footnotes (18)
- 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.
- F2. 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.
- F3. Shares sold pursuant to a 10b5-1 plan dated June 13, 2026.
- F4. Price reported is a weighted-average sales price. The shares were sold at prices ranging from $220.67 to $221.57. The Reporting Person will provide upon request to the SEC, the Issuer or security holder of the Issuer, full information regarding the number of shares sold at each separate price.
- F5. Price reported is a weighted-average sales price. The shares were sold at prices ranging from $221.68 to $222.65. The Reporting Person will provide upon request to the SEC, the Issuer or security holder of the Issuer, full information regarding the number of shares sold at each separate price.
- F6. Price reported is a weighted-average sales price. The shares were sold at prices ranging from $222.70 to $223.60. The Reporting Person will provide upon request to the SEC, the Issuer or security holder of the Issuer, full information regarding the number of shares sold at each separate price.
- F7. Price reported is a weighted-average sales price. The shares were sold at prices ranging from $223.82 to $224.81. The Reporting Person will provide upon request to the SEC, the Issuer or security holder of the Issuer, full information regarding the number of shares sold at each separate price.
- F8. Price reported is a weighted-average sales price. The shares were sold at prices ranging from $224.82 to $225.78. The Reporting Person will provide upon request to the SEC, the Issuer or security holder of the Issuer, full information regarding the number of shares sold at each separate price.
- F9. Price reported is a weighted-average sales price. The shares were sold at prices ranging from $225.96 to $226.54. The Reporting Person will provide upon request to the SEC, the Issuer or security holder of the Issuer, full information regarding the number of shares sold at each separate price.
- F10. Price reported is a weighted-average sales price. The shares were sold at prices ranging from $227.095 to $228.07. The Reporting Person will provide upon request to the SEC, the Issuer or security holder of the Issuer, full information regarding the number of shares sold at each separate price.
- F11. Price reported is a weighted-average sales price. The shares were sold at prices ranging from $228.13 to $229.12. The Reporting Person will provide upon request to the SEC, the Issuer or security holder of the Issuer, full information regarding the number of shares sold at each separate price.
- F12. Price reported is a weighted-average sales price. The shares were sold at prices ranging from $229.13 to $230.12. The Reporting Person will provide upon request to the SEC, the Issuer or security holder of the Issuer, full information regarding the number of shares sold at each separate price.
- F13. Price reported is a weighted-average sales price. The shares were sold at prices ranging from $230.13 to $231.11. The Reporting Person will provide upon request to the SEC, the Issuer or security holder of the Issuer, full information regarding the number of shares sold at each separate price.
- F14. Price reported is a weighted-average sales price. The shares were sold at prices ranging from $231.13 to $232.10. The Reporting Person will provide upon request to the SEC, the Issuer or security holder of the Issuer, full information regarding the number of shares sold at each separate price.
- F15. Price reported is a weighted-average sales price. The shares were sold at prices ranging from $232.13 to $233.12. The Reporting Person will provide upon request to the SEC, the Issuer or security holder of the Issuer, full information regarding the number of shares sold at each separate price.
- F16. Price reported is a weighted-average sales price. The shares were sold at prices ranging from $233.13 to $233.49. The Reporting Person will provide upon request to the SEC, the Issuer or security holder of the Issuer, full information regarding the number of shares sold at each separate price.
- F17. 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 2.
- F18. Price reported is a weighted-average sales price. The shares were sold at prices ranging from $230.13 to $231.10. The Reporting Person will provide upon request to the SEC, the Issuer or security holder of the Issuer, full information regarding the number of shares sold at each separate price.
Key Figures
Class B converted: 24,000 shares
Class A shares sold: 24,000 shares
Sale price range: $220.67–$233.49 per share
+2 more
5 metrics
Class B converted
24,000 shares
Class B Common Stock converted into Class A on September 14, 2026 by family trusts
Class A shares sold
24,000 shares
Total Class A Common Stock sold by family trusts on September 14, 2026
Sale price range
$220.67–$233.49 per share
Price ranges from weighted-average footnotes for September 14, 2026 sales
Rule 10b5-1 plan date
June 13, 2026
Plan under which the reported sales were executed
Remaining Class B holding
8,103 shares
Direct Class B Common Stock position reported after transactions, each convertible into one Class A share
Key Terms
Rule 10b5-1 plan, Class B Common Stock, Class A Common Stock, weighted-average sales price, +1 more
5 terms
Rule 10b5-1 plan regulatory
"Shares sold pursuant to a 10b5-1 plan dated June 13, 2026."
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"
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.
Class A Common Stock financial
"convertible at any time into one share of Class A Common Stock"
Class A common stock is a category of a company’s shares that carries a specific set of ownership rights—most commonly defined voting power and claims on dividends—set out in the company’s charter. For investors it matters because the class determines how much influence you have over corporate decisions, the share’s likely dividend and trading behavior, and how it compares in value to other share classes, like choosing a particular seat with different privileges at the company’s decision-making table.
weighted-average sales price financial
"Price reported is a weighted-average sales price."
Permitted Transfers regulatory
"except for certain "Permitted Transfers" as defined in the Issuer's amended"
FAQ
AI-generated questions and answers. How Rhea-AI works. Not financial advice.
What did Datadog (DDOG) disclose about its CFO’s insider transactions on this Form 4?
The CFO, David M. Obstler, reported family trusts converting 24,000 Class B shares into 24,000 Class A shares and selling 24,000 Class A shares on September 14, 2026, plus a remaining direct holding of 8,103 Class B shares.
Were the Datadog (DDOG) insider sales made under a Rule 10b5-1 plan?
Yes. Footnotes state that the reported Class A share sales were made pursuant to a Rule 10b5-1 plan dated June 13, 2026, indicating they followed a pre-established trading plan.
What Datadog (DDOG) holdings does the CFO still report after these transactions?
After these transactions, David M. Obstler reports a direct derivative position of 8,103 shares of Class B Common Stock, each convertible into one Class A share, as shown in the holdings and derivative summary information.
AI-generated analysis. How Rhea-AI works. Not financial advice.
