Callahan Michael James 4
4 · Datadog, Inc. · Filed Jun 16, 2026
Research Summary
AI-generated summary of this filing
Datadog (DDOG) Director Michael Callahan Sells 112,500 Shares
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.
Insider Transaction Report
Form 4
Datadog, Inc.DDOG
Callahan Michael James
Director
Transactions
- Conversion
Class A Common Stock
[F1][F2]2026-06-12+112,500→ 127,496 total(indirect: By Trust) - Sale
Class A Common Stock
[F3][F4][F2]2026-06-12$228.31/sh−6,715$1,533,092→ 120,781 total(indirect: By Trust) - Sale
Class A Common Stock
[F3][F5][F2]2026-06-12$229.50/sh−11,284$2,589,686→ 109,497 total(indirect: By Trust) - Sale
Class A Common Stock
[F3][F6][F2]2026-06-12$230.06/sh−28,701$6,603,015→ 80,796 total(indirect: By Trust) - Sale
Class A Common Stock
[F3][F7][F2]2026-06-12$231.30/sh−14,173$3,278,222→ 66,623 total(indirect: By Trust) - Sale
Class A Common Stock
[F3][F8][F2]2026-06-12$232.31/sh−18,830$4,374,482→ 47,793 total(indirect: By Trust) - Sale
Class A Common Stock
[F3][F9][F2]2026-06-12$233.37/sh−12,005$2,801,574→ 35,788 total(indirect: By Trust) - Sale
Class A Common Stock
[F3][F10][F2]2026-06-12$234.10/sh−16,145$3,779,517→ 19,643 total(indirect: By Trust) - Sale
Class A Common Stock
[F3][F11][F2]2026-06-12$235.49/sh−2,901$683,157→ 16,742 total(indirect: By Trust) - Sale
Class A Common Stock
[F3][F12][F2]2026-06-12$236.20/sh−1,746$412,409→ 14,996 total(indirect: By Trust) - Award
Class A Common Stock
[F13]2026-06-15+1,072→ 20,684 total - Conversion
Class B Common Stock
[F1][F2]2026-06-12−112,500→ 123,042 total(indirect: By Trust)→ Class A Common Stock (112,500 underlying)
Footnotes (13)
- [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.
- [F10]Price reported is a weighted-average sales price. The shares were sold at prices ranging from $233.85 to $234.84. 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 $234.86 to $235.85. 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 $235.90 to $236.65. 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.
- [F13]Represents the number of shares underlying Restricted Stock Units ("RSUs") granted pursuant to the Issuer's non-employee director compensation policy. Each RSU represents a contingent right to receive one share of Issuer's Class A common stock. The RSUs vest on the earlier of (A) the Company's next annual meeting of stockholders and (B) June 15, 2027, in each case, subject to the Reporting Person's continuous service to the Issuer through the vesting date.
- [F2]The Shares are held by The Callahan-Thernstrom Family Trust, of which Reporting Person is Trustee.
- [F3]Shares sold pursuant to a 10b5-1 plan dated March 13, 2026.
- [F4]Price reported is a weighted-average sales price. The shares were sold at prices ranging from $227.73 to $228.71. 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 $228.83 to $229.82. 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 $229.83 to $230.82. 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 $230.83 to $231.82. 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 $231.84 to $232.83. 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 $232.85 to $233.84. 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.
Signature
/s/ Kerry Acocella, Attorney-in-Fact|2026-06-16