DDOG
Datadog, Inc.
$45.60M
Cluster sell
Discretionary Insider Activity
Date:
05/29/2026
Insiders:
Jacobson Matthew, director, and 2 others
Prior trend:
6 months of no clear discretionary insider activity

Summary

A $45.60M cluster sell for Datadog, Inc. (DDOG) on 05/29/2026 after 6 months of no clear discretionary insider activity trend.

Reports

Action Amount Date Insider Role(s) SEC Filing No
Sell $10.00M 06/02/2026 Jacobson Matthew Director 0001193125-26-253541
Sell $34.33M 06/05/2026 Ittycheria Dev Director 0001561550-26-000188
Sell $1.27M 06/08/2026 COLE TITILOPE Director 0001561550-26-000190

Stake Changes

Action Insider Role(s) Total Change % Change
Sell Jacobson Matthew Director $10.00M 6.2%
Ittycheria Dev Director unknown unknown
Sell COLE TITILOPE Director $1.27M 80.8%

Transactions

Action Amount Date Insider Security Type SEC Code
Sell $5.00M 05/29/2026 Jacobson Matthew Class A Common Stock Discretionary Sale
Sell $4.80M 06/01/2026 Jacobson Matthew Class A Common Stock Discretionary Sale
Sell $195K 06/01/2026 Jacobson Matthew Class A Common Stock Discretionary Sale
06/03/2026 Ittycheria Dev Stock Option (Right to Buy) Non-discretionary Exercise/Conversion
06/03/2026 Ittycheria Dev Class B Common Stock Non-discretionary Exercise/Conversion
06/03/2026 Ittycheria Dev Class B Common Stock Non-discretionary Conversion
06/03/2026 Ittycheria Dev Class A Common Stock Non-discretionary Conversion
Sell $120K 06/03/2026 Ittycheria Dev Class A Common Stock Discretionary Sale
Sell $19.13M 06/03/2026 Ittycheria Dev Class A Common Stock Discretionary Sale
Sell $10.60M 06/03/2026 Ittycheria Dev Class A Common Stock Discretionary Sale
Sell $18K 06/03/2026 Ittycheria Dev Class A Common Stock Discretionary Sale
Sell $2.86M 06/03/2026 Ittycheria Dev Class A Common Stock Discretionary Sale
Sell $1.60M 06/03/2026 Ittycheria Dev Class A Common Stock Discretionary Sale
Sell $259K 06/04/2026 COLE TITILOPE Class A Common Stock Discretionary Sale
Sell $562K 06/04/2026 COLE TITILOPE Class A Common Stock Discretionary Sale
Sell $451K 06/04/2026 COLE TITILOPE Class A Common Stock Discretionary Sale

Stats

Prior max multiple:
3.3
Prior median multiple:
3.3

Metadata

Signal ID:
nFqsmC0JBvjUnaAq
Scanned on:
06/16/2026
Status:
Current