Five (FIVN) | News Based Sentiment Analysis

• On July 31, 2025, Five9 reported a strong second quarter, exceeding expectations with revenues of $283.27 million, a 12.4% year-over-year increase, and EPS of $0.76, surpassing the $0.65 consensus estimate. This performance, their best quarterly result since 2022, was driven by 16% growth in subscription revenue and a remarkable 42% jump in enterprise AI revenue, now representing over 20% of new enterprise ACV – signaling continued strength in their AI offerings.
• Following the strong Q2 results, Five9 raised its full-year 2025 revenue guidance to a midpoint of $1.1465 billion and increased its non-GAAP EPS guidance by $0.12 to $2.88, demonstrating confidence in sustained momentum. They also forecast Q3 revenue at a $284.5 million midpoint, further reinforcing their optimistic outlook.
• Five9 continues to solidify its position as a leader in the cloud contact center space, receiving recognition from both Opus Research on August 26, 2025, and Metrigy in August 2025 for their enterprise-focused approach to conversational AI. This industry validation builds on their existing accolades and reinforces their competitive advantage.
• Several Five9 executives sold shares in early September (September 4-5, 2025) – CFO Lee Bryan M. sold 1,889 shares for approximately $48,585 and CEO Mike Burkland sold 18,425 shares for $473,891 – but the company clarified these sales were solely to cover tax withholding obligations related to restricted stock unit vesting.
• As of September 6, 2025, a strong “Buy” consensus rating remains for Five9, with 33 analysts maintaining this position and a consensus price target of $64.03. Benzinga reported a consensus price target of $45.80 from 25 analysts, while MarketBeat indicated an average price target of $37.59 from 18 analysts, representing a potential upside of 42.11% from the price of $26.45 on August 30, 2025.
• Five9 was named a Leader in the 2025 Gartner Magic Quadrant for CCaaS for the eighth consecutive time on September 10, 2025, highlighting their consistent innovation and ability to deliver customer experiences. The Five9 Intelligent CX Platform, powered by Five9 Genius AI, offers a comprehensive suite of solutions for various enterprise sizes.
• Five9 was also rated “Innovative” in various categories within the 2025 ISG Buyers Guides for Contact Centers on September 8, 2025, including Contact Centers for Retail and Healthcare, reflecting innovation in AI-driven automation and advanced analytics.
• Insider sales continued throughout September, with Tiffany Meriweather selling 7,861 shares on September 4th for $202,184.92 and Andy Dignan selling 8,314 shares between September 4th and 5th for approximately $212,514. These sales, like those earlier in the month, were partially related to Rule 10b5-1 plans.

The Investment Story: Five9 continued to demonstrate strong financial performance and industry leadership throughout September 2025, bolstered by positive analyst coverage and recognition in key industry reports. While insider selling occurred, it was largely attributed to tax obligations and pre-planned trading plans, minimizing concerns.

What It Means for Investors: The consistent positive developments suggest Five9 is well-positioned for continued growth in the cloud contact center market. The high analyst price targets indicate significant upside potential, but investors should continue to monitor insider trading activity and the ongoing CEO succession plan.

Looking Ahead: Investors should watch for Five9’s Q3 2025 earnings report to assess continued momentum and the impact of recent industry recognition. The appointment of a new CEO, expected by the end of 2025, will also be a key event to monitor.

The Bottom Line: Five9 remains a compelling investment opportunity, demonstrating strong financial results, innovative technology, and a stable leadership transition. Despite the insider selling, the overall outlook is positive, making it a stock to watch for investors seeking exposure to the growing cloud contact center space.