One Fund Places an $8.5 Million Bet on Five9 Despite a 50% Decline in Stock Over the Past Year
Written by Emily J. Thompson, Senior Investment Analyst
Updated: Dec 19 2025
0mins
Should l Buy FIVN?
Source: NASDAQ.COM
S Squared Technology's Investment: S Squared Technology increased its holdings in Five9 by 165,000 shares in Q3, bringing its total to 350,000 shares valued at $8.5 million, which represents 3.2% of the fund's assets under management.
Five9's Financial Performance: Despite a significant drop in stock price over the past year, Five9 reported an 8% year-over-year revenue increase to $285.8 million, with a notable 41% surge in Enterprise AI revenue and improved profitability margins.
Market Position and Strategy: Five9's stock has underperformed compared to the S&P 500, but its recent financial results suggest a stabilization in business fundamentals, prompting S Squared's investment as a calculated move rather than a core holding.
Technological Advancements: Five9 is recognized for its cloud software solutions for contact centers, utilizing advanced technologies like natural language processing and automatic speech recognition to enhance customer interactions and drive growth.
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Analyst Views on FIVN
Wall Street analysts forecast FIVN stock price to rise over the next 12 months. According to Wall Street analysts, the average 1-year price target for FIVN is 35.50 USD with a low forecast of 25.00 USD and a high forecast of 59.00 USD. However, analyst price targets are subjective and often lag stock prices, so investors should focus on the objective reasons behind analyst rating changes, which better reflect the company's fundamentals.
20 Analyst Rating
15 Buy
5 Hold
0 Sell
Strong Buy
Current: 16.010
Low
25.00
Averages
35.50
High
59.00
Current: 16.010
Low
25.00
Averages
35.50
High
59.00
About FIVN
Five9, Inc. helps organizations to create hyper-personalized and artificial intelligence (AI)-driven customer experiences. The Company's Intelligent CX Platform, powered by Five9 Genius AI, delivers a suite of applications that enable a range of customer service, sales, and marketing functions. It delivers an end-to-end cloud software solution for contact centers. The Company's solution allows simultaneous management and optimization of customer interactions across voice, chat, email, Web, social media and mobile channels, either directly or through its application programming interfaces. The Company's product categories include Core Cloud, AI & Automation, Employee Engagement and Customer Engagement. Its Core Cloud products include Global Voice, Agent Desktop Plus, Supervisor Plus, CRM Integrations and UC Integrations. Its AI & Automation products include Artificial Intelligence, AI Agents, AI Insights, AI Knowledge, GenAI Studio, Workflow Automation and Reporting & Analytics.
About the author
Emily J. Thompson
Emily J. Thompson, a Chartered Financial Analyst (CFA) with 12 years in investment research, graduated with honors from the Wharton School. Specializing in industrial and technology stocks, she provides in-depth analysis for Intellectia’s earnings and market brief reports.
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- Intelligent Interactions: The new solution enables faster, personalized customer interactions by integrating workflows, analytics, and AI support, allowing enterprises to deliver seamless, intelligent customer experiences across all channels.
- Strengthened Market Strategy: The partnership includes a reinforced go-to-market strategy aimed at modernizing customer experiences across industries such as retail, financial services, and healthcare, while simplifying procurement through Google Cloud Marketplace.
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- Partnership Expansion: Five9 has expanded its partnership with Google Cloud to launch a joint Enterprise CX AI solution, integrating Five9's AI-Infused Intelligent CX Platform with Google’s Gemini models to enhance customer experiences for large organizations.
- Intelligent Interactions: The new solution enables faster, personalized customer interactions by integrating workflows, analytics, and AI support, allowing enterprises to deliver seamless, intelligent customer experiences across all channels.
- Strengthened Market Strategy: The partnership includes a reinforced go-to-market strategy aimed at modernizing customer experiences across industries such as retail, financial services, and healthcare, while simplifying procurement through Google Cloud Marketplace.
- CEO Transition: Five9 announced that Amit Mathradas will succeed Mike Burkland as CEO on February 2, 2026, following Burkland's planned retirement, marking a significant leadership change for the company.
See More
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- Market Stability Expectations: Wall Street broadly anticipates that the annual inflation rate will remain stable at 2.7% in December, with a monthly increase of 0.3%, indicating sustained investor confidence in the economic outlook, which helps maintain market sentiment.
- Bond Yield Dynamics: The 10-year Treasury bond yield stands at 4.19%, while the 2-year bond is at 3.55%, reflecting market expectations for stable future interest rate policies that could influence stock market liquidity and investment decisions.
- Alphabet's Market Value Milestone: Alphabet Inc. reached a market value of $4 trillion amid the AI boom, with its stock rising 0.68%, which not only highlights the company's leadership in technological innovation but also may attract more investor attention to its future growth potential.
- Xpeng's Supply Chain Strategy: Despite a 2.63% drop in Xpeng Inc.'s stock price, the announcement to establish independent localized supply chain teams by 2026 demonstrates the company's strategic commitment to global market expansion and supply chain management.
See More
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- Investor Conference Participation: Five9 will present at the 28th Annual Needham Growth Conference on January 13, showcasing its Intelligent CX Platform, which is expected to attract investor interest and enhance market confidence.
- Platform Advantage Showcase: The Five9 Intelligent CX Platform, powered by Five9 Genius AI, is trusted by over 3,000 customers and 1,400 partners, further solidifying its market position in AI-driven customer experience.
- Customer Experience Innovation: By delivering hyper-personalized and effortless customer experiences, Five9 enables organizations to achieve better business outcomes, highlighting its strategic importance in enhancing customer satisfaction and loyalty.
- Global Influence Expansion: The widespread application of Five9's platform globally signifies its critical role in driving digital transformation in the industry and improving customer engagement efficiency.
See More
Five9 President Dignan Sells 8,212 Shares for ~$166,700
- Direct Holdings Reduction: Five9 President Andy Dignan sold 8,212 shares between December 4 and 5, 2025, for approximately $166,700, reducing his direct holdings from 216,025 to 207,813 shares, indicating a potential lack of confidence in the company's future prospects.
- Execution of Trading Plan: The transaction was executed under a Rule 10b5-1 plan, ensuring transparency and compliance, with over 3,000 shares sold to cover tax obligations, reflecting Dignan's cautious financial management.
- Poor Market Performance: Five9's stock plummeted over 50% in 2025, while the S&P 500 rose nearly 18%, highlighting significant challenges the company faces in the competitive cloud software market, which may affect investor confidence.
- Strategic Restructuring Context: The company has undergone significant restructuring, including workforce reductions and executive departures, with rumors of a potential sale, indicating pressure on management to explore strategic alternatives.
See More
Five9 President Sells 8,212 Shares for Approximately $166,700
- Executive Trading Activity: Five9 President Andy Dignan sold 8,212 shares on December 4 and 5, 2025, for a total of approximately $166,700, indicating a potential decrease in confidence regarding the company's future prospects.
- Ownership Stake Change: Following the transaction, Dignan's direct holdings decreased from 216,025 to 207,813 shares, equating to a post-sale value of about $4.29 million, suggesting a diminishing influence within the company.
- Transaction Context Analysis: This sale was substantially larger than Dignan's recent median sale of 700 shares, representing 3.8% of his direct holdings, which exceeds the typical 0.32% median seen in his recent sales, possibly indicating a reassessment of market conditions.
- Market Performance Warning: Five9's stock has declined over 50% in 2025 while the S&P 500 rose nearly 18%, highlighting a decrease in the company's competitive position in the industry, which may affect investor confidence.
See More
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- Surge in Options Volume: UnitedHealth Group (UNH) sees an options volume of 67,042 contracts today, equating to approximately 6.7 million shares, which represents a significant 106.2% of its average daily trading volume over the past month, indicating strong market interest in its future performance.
- High-Frequency Trading Insights: Notably, the $330 strike call option expiring on December 26, 2025, has traded 5,018 contracts today, representing about 501,800 shares of UNH, suggesting bullish sentiment among investors at this price level.
- Increased Market Activity: In comparison, Mineralys Therapeutics Inc (MLYS) has an options volume of 15,285 contracts today, approximately 1.5 million shares, which is close to 98.8% of its average daily trading volume over the past month, indicating investor interest in this company as well.
- Investor Sentiment Analysis: The $60 strike call option for MLYS expiring on March 20, 2026, has seen a trading volume of 5,108 contracts today, representing around 510,800 shares, reflecting positive market expectations regarding its future potential.
See More
