Datadog CEO Olivier Pomel Has Sold $1.2 Billion in DDOG Stock Since IPO

1,063 Form 4 Filings in Five Years

Olivier Pomel, the co-founder and CEO of Datadog (DDOG), has sold $1.2 billion in company stock since the September 2019 IPO. Across 1,063 Form 4 transactions — averaging one filing every 2.2 days — Pomel has maintained one of the most active insider selling programs in the cloud software sector.

His most recent sales, in December 2025, generated approximately $6.4 million across two batches at prices between $137 and $156 per share. Despite the constant selling, Pomel still holds roughly 8.5 million shares worth an estimated $1.2 billion at current prices.

December 2025 Sales

Date	Type	Shares Sold	Avg Price	Est. Value
Dec 3	Exercise + Sell	~33,000	$154	$5.0M
Dec 17	Sell	~11,000	$138	$1.4M
Total		~44,000		$6.4M

The December 3 batch included option exercises at just $0.91 per share — founder-era grants from before Datadog was public. Selling those shares at $154 represents a 16,800% gain per option. Even the December 17 sales at $138 delivered extraordinary returns on sub-$1 options.

The Cadence: A Filing Every 2.2 Days

What distinguishes Pomel’s selling from most CEO programs is the sheer volume of filings. With 1,063 transactions in approximately five and a half years, he averages a new Form 4 filing roughly every two business days. The filings span open-market sales (S), option exercises (M), stock conversions (C), and charitable gifts (G).

This frequency is by design. Pre-arranged 10b5-1 trading plans allow insiders to sell in small, frequent lots rather than large blocks — reducing market impact and providing steady liquidity. Pomel’s plan appears to trigger sales on nearly every trading day the stock trades within a predetermined range.

Career Numbers

• Total sell proceeds: $1.204 billion since September 2019
• Total purchases: $0 (all shares from compensation and founder grants)
• Transaction count: 1,063 Form 4 filings
• Remaining direct shares: ~518,000
• Remaining indirect shares: ~7.96 million (trusts, entities)
• Total remaining value: ~$1.2 billion at $140/share

The near-equal split between what Pomel has sold ($1.2B) and what he still holds ($1.2B) suggests a deliberate 50/50 diversification strategy — exactly the kind of rational wealth management that financial advisors recommend for concentrated single-stock positions.

Datadog’s Rise

Pomel co-founded Datadog in 2010 as a cloud monitoring platform. The company IPO’d in September 2019 at $27 per share, raising $648 million. DDOG now trades near $140 — a 420% return from IPO price — and has a market capitalization exceeding $45 billion.

The stock has been volatile: it peaked above $196 in November 2021, crashed to $62 in October 2022, and has oscillated between $80 and $160 since. Through every phase, Pomel’s selling program has continued without pause — selling at $196 highs and $80 lows alike.

What to Watch

• Selling pace — At $6.4M per month, Pomel could sell another $75M+ in 2026. Any acceleration or deceleration would signal changes in his 10b5-1 plan.
• Gift activity — Pomel gifted 348,000 shares in December 2025, suggesting active charitable or estate planning alongside the sales program.
• Stock-based compensation — A February 2026 award of 255,610 shares replenishes his direct holdings, partially offsetting sales.
• DDOG earnings — As CEO, Pomel enters blackout periods around quarterly reports. Sales tend to cluster in the weeks after earnings.

Track Olivier Pomel’s insider transactions on his 13F Insight profile, or view institutional holders of Datadog on the DDOG stock detail page.