Datadog (DDOG) CFO David M. Obstler Sells 24,000 Shares

What Happened
David M. Obstler, Datadog’s Chief Financial Officer, converted Class B shares into Class A common stock and sold a total of 24,000 shares in multiple open‑market trades on September 14, 2026. The sales generated approximately $5,459,447 in proceeds (weighted‑average sale price ≈ $227.48 per share). Reported sale prices across the transactions ranged roughly from about $220.67 to $233.49 (see footnotes for per‑batch ranges). The conversions reflect the Class B → Class A conversion provision (no cash paid on conversion); the open‑market sales are routine dispositions, many executed under a pre‑arranged 10b5‑1 plan.

Key Details

• Transaction date: September 14, 2026 (Form 4 filed Sept 16, 2026 — timely).
• Aggregate sold: 24,000 shares; aggregate proceeds ≈ $5,459,447; weighted‑avg price ≈ $227.48.
• Price range (per footnotes): approximately $220.67 to $233.49 across different trade lots; several lots reported as weighted‑average prices for groups of trades.
• Conversions: Class B common stock converted to Class A (footnote F1) prior to/around the sales; conversions recorded at $0 (no cash).
• 10b5‑1 plan: Portions of the sales were made pursuant to a 10b5‑1 trading plan dated June 13, 2026 (footnote F3).
• Trust holdings: Some shares referenced are held in trusts for the reporting person’s children (footnotes F2, F17).
• Filing note: This filing is the second of two forms due to the 30‑line Table I limit (remarks).

Context: Converting Class B to Class A is administrative (no cash outlay) and common where Class B shares are convertible; the subsequent open‑market sales are disposals and do not, by themselves, imply insider sentiment. Sales executed under a 10b5‑1 plan are pre‑arranged and typically indicate routine planned selling. The Form 4 does not disclose total post‑sale holdings in the excerpt provided.