Five9 President Reduces Stake After 50% Drop in 2025

Andy Dignan, President of Five9 (NASDAQ:FIVN), directly sold 8,212 shares on Dec. 4 and Dec. 5, 2025, for a total consideration of approximately $166,700, according to an SEC Form 4 filing.

Transaction summary

Transaction value based on SEC Form 4 weighted average purchase price ($20.30); post-transaction value based on the Dec. 5, 2025 closing price.

Key questions

• How does this sale compare to Dignan's historical trading activity?
  This transaction was substantially larger than Dignan's recent median sale of 700 shares, and at 3.8% of direct holdings, it exceeded the 0.32% median percentage typically seen in his recent sales since March 2025.
• What was the impact on Dignan's ownership position?
  Dignan's direct holdings decreased from 216,025 to 207,813 shares; this equates to a post-sale direct stake valued at approximately $4.29 million as of Dec. 5, 2025.
• Were derivative instruments or indirect entities involved in this transaction?
  No options were exercised and no shares flowed through trusts or other indirect entities; all shares disposed were held and sold directly.
• Does the trade size reflect a change in strategy or simply capacity constraints?
  While the absolute trade size was high, Dignan's holdings have declined over time, so larger recent transactions reflect both a tactical uptick and a response to the shrinking share base, as evidenced by a holdings reduction of 11.49% in the recent period.

Company overview

* 1-year performance is calculated using Dec. 5, 2025 as the reference date.

Company snapshot

• Provides a cloud-based contact center platform supporting voice, video, chat, email, social media, and API integrations, with advanced features such as natural language processing and automatic speech recognition.
• Serves clients across banking, financial services, business process outsourcing, consumer, healthcare, technology, and education sectors.

Five9 operates at scale in the cloud software industry, delivering mission-critical contact center solutions to a diverse global client base. The company leverages advanced AI-driven technologies to enhance customer engagement and operational efficiency. Its strategic focus on multi-channel communication and robust cloud infrastructure positions it as a competitive provider in the software infrastructure market.

What this transaction means for investors

Dignan's share sale was part of a Rule 10b5-1 corporate trading plan, which allows company insiders to transact shares of their company on a predetermined schedule, removing the appearance of insider trading. In fact, more than 3,000 shares from this transaction were sold to cover the tax withholding obligation connected to the trading plan.

Five9 stock ended 2025 down more than 50%, while the benchmark S&P 500 was up nearly 18%. The company has gone through a significant restructuring over the past year, reducing its workforce and seeing the departure of several executives. There have also been whispers that a sale could be on the horizon, as activist shareholders such as Anson Funds and Legion Partners are reportedly encouraging management to look at "strategic alternatives," according to CX Today. The company has also appointed a new CEO, Amit Mathradas, who will take the lead effective Feb. 2.

Five9 is certainly operating in an attractive industry, providing cloud software support to businesses in the defensive banking, financial services, consumer, healthcare, and education sectors, as well as tech companies. The stock continues to lag the overall market, which itself is being propped up by investor interest in tech solutions, which could be a warning sign for investors. However, for aggressive investors who believe in the company's ability to rebound, or who see it as a strong candidate for a sale, today's price could be an attractive entry point.

Glossary

Direct holdings: Shares owned and controlled personally by an individual, not through trusts or other entities.
Indirect entities: Organizations or accounts, such as trusts, that hold shares on behalf of an individual.
Derivative instruments: Financial contracts whose value depends on the price of an underlying asset, such as options or futures.
Disposition: The act of selling or otherwise transferring ownership of an asset.
Open-market sale: Selling shares through public stock exchanges at prevailing market prices.
Form 4: A required SEC filing disclosing insider trades by company officers, directors, or major shareholders.
Weighted average price: The average price per share in a transaction, weighted by the number of shares sold at each price.
Post-transaction: Refers to the status or values after a specific trade or transaction has occurred.
Tactical cadence: The timing and frequency of transactions, reflecting changes in strategy or market conditions.
Cloud-based contact center platform: A customer service system hosted online, enabling communication across multiple channels.
Natural language processing: Artificial intelligence technology that enables computers to understand and interpret human language.
TTM: The 12-month period ending with the most recent quarterly report.

Sarah Sidlow has no position in any of the stocks mentioned. The Motley Fool has positions in and recommends Five9. The Motley Fool has a disclosure policy.