Form 4: Five9 CEO Sells Shares for Tax Obligations

Five9, Inc. CEO Michael Burkland sold 17,992 shares of common stock at a weighted average price of $20.35 to cover tax withholding obligations related to restricted stock unit vesting.

Summary

• Chief Executive Officer Michael Burkland of Five9, Inc. sold 17,992 shares of common stock.
• The transaction occurred on December 4, 2025, at a weighted average price of $20.35 per share.
• This sale was a non-discretionary transaction mandated by Five9, Inc. to cover tax withholding obligations in connection with the vesting and settlement of restricted stock units.
• The transaction was executed pursuant to a Rule 10b5-1(c) plan.
• Following the sale, Mr. Burkland directly beneficially owns 349,570 shares and indirectly beneficially owns 133,026 shares through a trust.

Sentiment

Score: 6

Explanation: The sentiment is neutral to slightly positive. The transaction is a routine, non-discretionary sale to cover tax obligations upon RSU vesting, which is a common occurrence for executives. It does not reflect a change in management's outlook or confidence in the company's future.

Positives

• The sale was explicitly stated as a non-discretionary transaction, indicating it was not a voluntary decision by the CEO to reduce his stake due to concerns about the company's performance or future outlook.
• The transaction was pre-planned under a Rule 10b5-1(c) plan, which provides an affirmative defense against insider trading allegations and demonstrates transparency.

Negatives

• A reduction in the CEO's direct beneficial ownership by 17,992 shares occurred.

Risks

• While a routine tax-related sale, any insider selling can sometimes be misinterpreted by the market as a lack of confidence, potentially leading to short-term negative sentiment.

Future Outlook

NA

Management Comments

• The sale reported on this form represents a Five9, Inc. mandated sale by the Reporting Person to cover tax withholding obligations in connection with the vesting and settlement of restricted stock units, and it does not represent a discretionary trade by the Reporting Person.

Industry Context

This type of insider transaction, where executives sell shares to cover tax obligations upon the vesting of equity awards, is a routine and common practice across all industries for publicly traded companies.

Comparison to Industry Standards

• The practice of executives selling a portion of vested equity awards to cover tax liabilities is a standard and widely accepted practice across global benchmarks for executive compensation. It is not indicative of unique company-specific issues or performance relative to peers.

Stakeholder Impact

• Shareholders: The sale is a routine tax-related event and is unlikely to have a significant long-term impact on shareholder value, though short-term market sentiment might be affected if the transaction is misinterpreted as a discretionary sale.

Key Dates

Recommendation

The reported transaction is a non-discretionary sale by the CEO to cover tax obligations arising from the vesting of restricted stock units. This is a common and expected event for executives receiving equity compensation and does not reflect a change in the company's fundamentals or management's confidence. Therefore, this filing alone does not warrant a change in investment recommendation.

Keywords

Five9, FIVN, Michael Burkland, CEO, Insider Trading, Form 4, Stock Sale, Restricted Stock Units, Tax Withholding, 10b5-1 Plan