Callahan Michael James 4

What Happened

• Michael J. Callahan, a Datadog director, converted 112,500 shares of Class B common stock into Class A common stock and sold all 112,500 resulting shares in multiple open-market transactions on June 12, 2026. The sales generated approximately $26.06 million in proceeds (aggregate of several block sales with weighted-average prices reported). On June 15, 2026 he was also granted 1,072 restricted stock units (RSUs) under the company’s non-employee director compensation program (no purchase price; vesting by the next annual meeting or June 15, 2027, subject to continued service).

Key Details

• Transaction dates: conversion and all sales on June 12, 2026; RSU grant on June 15, 2026. Filing date: June 16, 2026 (filed within the normal Form 4 window).
• Shares sold: nine open-market sale lots totaling 112,500 shares. Reported weighted-average prices per lot range from about $228.31 up to $236.20; aggregate proceeds ≈ $26.06M.
• Conversion: The 112,500-share conversion was of Class B common stock to Class A (each Class B share converts 1:1 to Class A; see footnote F1).
• Plan/schedule: Sales were made pursuant to a pre-established 10b5-1 plan dated March 13, 2026 (footnote F3).
• Grant: 1,072 RSUs awarded (footnote F13); each RSU represents one share upon vesting.
• Shares owned after transaction: not specified in this report.
• Footnotes: several sale lots report weighted-average prices and give price ranges on request (F4–F12). The Class B conversion conditions are described in F1; shares are held by The Callahan‑Thernstrom Family Trust (F2).

Context

• The filing shows a conversion of founder/insider Class B stock followed by planned open-market sales under a 10b5-1 plan — a common way insiders monetize shares while reducing the risk of accusations of trading on material nonpublic information. The RSU grant is routine director compensation and vests based on continued service. This report is factual and does not indicate the insider’s motives.