Form 4: Datadog CFO Executes Pre-Planned Stock Sale and Option Exercise

Datadog, Inc.'s Chief Financial Officer, David M. Obstler, reported the exercise of stock options and the subsequent sale of 20,000 Class A Common Stock shares under a Rule 10b5-1 trading plan.

Summary

• Datadog, Inc. CFO David M. Obstler reported transactions involving the company's Class A and Class B Common Stock on June 4, 2025.
• Mr. Obstler exercised a fully vested stock option to acquire 20,000 shares of Class B Common Stock at an exercise price of $1.55 per share.
• Concurrently, these 20,000 Class B shares were converted into 20,000 shares of Class A Common Stock, effectively acquiring Class A shares at $1.55 per share.
• Immediately following the acquisition, Mr. Obstler disposed of 20,000 shares of Class A Common Stock at a price of $120.25 per share.
• The sale was executed pursuant to a Rule 10b5-1 trading plan established on June 12, 2024.
• Following these transactions, Mr. Obstler directly holds 399,270 shares of Class A Common Stock and 65,000 shares of Class B Common Stock (from the option exercise), 35,603 shares of Class B Common Stock, and 15,603 shares of Class B Common Stock.
• An additional 92,397 shares of Class A Common Stock are held indirectly by the Obstler Children 2019 Trust.

Sentiment

Score: 4

Explanation: The sentiment is slightly negative due to the insider sale by a key executive, despite it being a pre-planned transaction under a 10b5-1 plan. The exercise of options at a low price is positive for the insider but neutral for the company's immediate outlook.

Positives

• The exercise of stock options at a significantly low price of $1.55 per share, compared to the sale price of $120.25, indicates a substantial realized gain for the CFO on these specific shares.
• The transaction was conducted under a pre-arranged Rule 10b5-1 plan, which provides a defense against insider trading allegations and suggests a planned liquidity event rather than a reaction to new, negative information.

Negatives

• The disposition of 20,000 shares by a key executive, the Chief Financial Officer, could be perceived negatively by some investors, potentially signaling a lack of confidence or a move to diversify holdings, despite being part of a pre-planned trading arrangement.

Risks

• Insider selling, even under a 10b5-1 plan, can sometimes lead to negative market sentiment or speculation about the company's future prospects among investors.

Future Outlook

NA

Industry Context

This filing is a routine disclosure of an insider stock transaction, common across all industries for publicly traded companies, and does not provide specific industry-related insights.

Comparison to Industry Standards

• NA

Corporate Governance

Related Party Transactions

• Shares are held indirectly by the Obstler Children 2019 Trust, of which the Reporting Person's spouse is Trustee, indicating a related party holding.

Stakeholder Impact

• Shareholders may react to the insider sale, potentially influencing short-term stock price movements due to sentiment.

Key Dates

Recommendation

Keywords

Datadog, DDOG, SEC Form 4, Insider Trading, Stock Sale, Option Exercise, David Obstler, CFO, 10b5-1 Plan, Class A Common Stock, Class B Common Stock