Form 4: Datadog CFO Sells Shares
Insider Transaction (Form 4)
David M Obstler, Chief Financial Officer of Datadog, Inc., sold 16,000 shares of common stock on September 21, 2026 for $241.25 per share.
Summary
- Open-market sale: disposed of 10,000 Class A Common Stock at $241.25 ($2,412,500) on September 21, 2026; holds 368,067 after (Direct).
- Conversion of derivative: acquired 3,000 Class A Common Stock on September 21, 2026; holds 3,000 after (Indirect).
- Open-market sale: disposed of 3,000 Class A Common Stock at $241.25 ($723,750) on September 21, 2026 (Indirect).
- Conversion of derivative: acquired 3,000 Class A Common Stock on September 21, 2026; holds 3,000 after (Indirect).
- Open-market sale: disposed of 3,000 Class A Common Stock at $241.25 ($723,750) on September 21, 2026 (Indirect).
- Conversion of derivative: disposed of 3,000 Class B Common Stock on September 21, 2026; holds 31,198 after (Indirect).
- Conversion of derivative: disposed of 3,000 Class B Common Stock on September 21, 2026; holds 31,199 after (Indirect).
Sentiment
Score: 4
Explanation: StockSavvy.ai views this as a mildly negative but low-conviction signal: an insider sold $3,860,000 of stock under a pre-arranged Rule 10b5-1 plan, which is typically routine.
Insider Transactions
David M Obstler — Officer (Chief Financial Officer)
Transaction made under a Rule 10b5-1 trading plan.
| Date | Transaction | Security | Shares | Price | Value | Held After |
|---|---|---|---|---|---|---|
| 2026-09-21 | Open-market sale | Class A Common Stock | 10,000 | $241 | $2.4M | 368,067 |
| 2026-09-21 | Conversion of derivative | Class A Common Stock | 3,000 | — | — | 3,000 |
| 2026-09-21 | Open-market sale | Class A Common Stock | 3,000 | $241 | $723.8K | 0 |
| 2026-09-21 | Conversion of derivative | Class A Common Stock | 3,000 | — | — | 3,000 |
| 2026-09-21 | Open-market sale | Class A Common Stock | 3,000 | $241 | $723.8K | 0 |
| 2026-09-21 | Conversion of derivative | Class B Common Stock | 3,000 | — | — | 31,198 |
| 2026-09-21 | Conversion of derivative | Class B Common Stock | 3,000 | — | — | 31,199 |
Key Dates
| Date | Description |
|---|---|
| 2026-09-21 | Open-market sale (10,000 shares) |
| 2026-09-21 | Conversion of derivative (3,000 shares) |
| 2026-09-21 | Open-market sale (3,000 shares) |
| 2026-09-21 | Conversion of derivative (3,000 shares) |
| 2026-09-21 | Open-market sale (3,000 shares) |
| 2026-09-21 | Conversion of derivative (3,000 shares) |
| 2026-09-21 | Conversion of derivative (3,000 shares) |
Keywords
insider transaction, Form 4, DDOG, Datadog, Inc., bearish, David M Obstler
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