Callahan Michael James 4

What Happened

• Michael James Callahan, a director of Datadog, converted 12,500 shares of Class B common stock into Class A and sold 12,500 Class A shares in an open-market transaction on June 29, 2026. The shares sold fetched $247.47 per share for proceeds of $3,093,375. The filing also reports a derivative conversion of 12,500 shares at $0.00 (reflecting the Class B→Class A conversion).

Key Details

• Transaction date: June 29, 2026. Form 4 filed July 1, 2026 (appears timely within the SEC two-business-day window).
• Sale: 12,500 shares at $247.47 per share — total proceeds $3,093,375.
• Conversions: Reporting shows conversion (code C) of 12,500 Class B shares into Class A; one conversion line lists $0.00, indicating no cash payment for conversion.
• Shares sold pursuant to a 10b5-1 trading plan dated March 13, 2026 (footnote F3).
• Shares were held by The Callahan‑Thernstrom Family Trust, of which Callahan is Trustee (footnote F2).
• Post-transaction holdings: not disclosed in the provided excerpt.

Context

• The reported activity is a conversion of convertible Class B stock followed by an immediate open-market sale under a prearranged 10b5-1 plan. Such preplanned sales are commonly routine and do not, by themselves, indicate the insider’s change in view about the company; purchases tend to be more indicative of a bullish insider signal.