Key points
- Two Datadog directors sold 79,424 shares for $19.99 million on Aug. 13, 2026.
- Matthew Jacobson, a director since 2019 and a partner at ICONIQ Growth, sold the most, 59,424 shares for $15.0 million, with no 10b5-1 plan behind it.
- Amit Agarwal, Datadog's former president and now a director, sold 20,000 shares for $4.99 million under a plan he set in March.
- Agarwal's filing records an acquisition next to the sales, but no shares were bought. It was a routine conversion of Class B stock to Class A right before he sold.
- DDOG hit $292.72 on Aug. 5, fell about 19% the next day on earnings, and traded near $252 when the directors sold.
Two Datadog (DDOG) directors sold stock on the same day, Aug. 13, about $20 million between them. What pulled me in was how differently they went about it. One had set his sale up months earlier and let it run on its own. The other looked at the stock that week and decided, on the spot, to sell $15 million.
The two sellers have more in common than a board seat. Matthew Jacobson has sat on Datadog's board since 2019 and is a partner at ICONIQ Growth, the venture firm that backed Datadog years before it went public. Amit Agarwal ran Datadog as president for more than a decade, stepped down at the end of 2024, and joined ICONIQ Growth as a general partner in early 2025. He kept his board seat on the way out. So both names on these filings are Datadog directors and ICONIQ partners, and both sold the same day.
Between them they sold 79,424 shares for $19.99 million.
| Director | Role as filed | Shares sold | Value | 10b5-1 plan? |
|---|---|---|---|---|
| Matthew Jacobson | Director | 59,424 | $14,999,792 | No |
| Amit Agarwal | Director | 20,000 | $4,986,341 | Yes, set March 13 |
One line on Agarwal's form is worth reading slowly, because it can trip you up. Right before the sale, the filing records an acquisition of 20,000 shares. He didn't buy them. He converted 20,000 shares of Datadog's Class B stock into Class A, the kind that trades on the exchange, and sold those same shares the same afternoon. The acquisition and the sale offset each other. On paper it shows a buy and a sale, but it was one sale.
The line I kept coming back to is the plan box. A checkbox near the top of a Form 4 marks whether the trade was "intended to satisfy the affirmative defense conditions of Rule 10b5-1(c)," the SEC's phrase for a schedule locked in ahead of time. Agarwal's is checked, and his plan is dated March 13, 2026. He set the terms in the spring, and the sale ran on its own five months later. Jacobson's box is blank, so the date was his to pick. He looked at the stock in August and chose to sell $15 million of it. We wrote up what that box means for a shareholder in a separate piece.
Where the stock stood when they sold
It helps to know the backdrop. Datadog had a monster year, up from about $98 in late February to a high of $292.72 on Aug. 5. The next morning it reported second-quarter results, beat Wall Street on both revenue and profit, and fell hard anyway, from $283.17 the day before to $229.29 that day, as investors fixed on a softer growth outlook. We covered that earnings day when it happened. By Aug. 13 the stock had recovered into the low $250s, and that's where the selling took place. Jacobson's shares went at weighted-average prices from about $249 to $257, Agarwal's from about $241 to $253.
A Form 4 records the trade and leaves the reason off the page. Both men still own a lot of Datadog. Jacobson holds 524,708 shares in trusts, and Agarwal keeps more than 630,000 shares of Class B, the extra-vote stock founders and early insiders hang onto, even after this sale. People sell to cover a tax bill or to buy a house, and plenty sell for the plain reason that too much of their money sits in one stock. A partner whose day job is now funding startups has ordinary uses for cash. What the filings show cleanly is two directors selling, one on a plan set in March and one on his own read in August. The acquisition on Agarwal's form was a share conversion, not a bet on the stock. We ran the same check on another name this month, the chip-test maker Aehr, where five insiders sold with no plan at all. Fresh Datadog filings reach our insider tracker as they post, and the company's full insider-filing history sits on its DDOG stock page.
Sources
- SEC Form 4 for Matthew Jacobson filed Aug. 17, 2026 (accession 0001193125-26-354158), 59,424 Class A shares sold Aug. 13 at weighted-average prices from $248.7894 to $256.7448, 524,708 shares held through trusts afterward, Rule 10b5-1 box unchecked
- SEC Form 4 for Amit Agarwal filed Aug. 17, 2026 (accession 0001540517-26-000002), conversion of 20,000 Class B shares to Class A and sale of 20,000 Class A shares on Aug. 13 at weighted-average prices from $241.29 to $253.1615, sold under a Rule 10b5-1 plan dated March 13, 2026, held by the Agarwal 2018 Family Trust, 636,440 Class B shares held afterward
- Both filings for Datadog, Inc. (CIK 0001561550), period of report Aug. 13, 2026
- DDOG daily closing prices, Feb. through Aug. 2026: 52-week low $98.01 on Feb. 24, high $292.72 on Aug. 5, close $283.17 on Aug. 5 and $229.29 on Aug. 6, close $252.24 on Aug. 13
- Datadog second-quarter 2026 results reported Aug. 6, 2026: revenue $1.12 billion, up 35.6% year over year, earnings of $0.65 a share
- ICONIQ Growth announcement naming Amit Agarwal a general partner, January 2025; Datadog proxy statement listing Matthew Jacobson as a director since July 2019
