FIVN Five9 Inc

This article compares Datadog (DDOG) and Five9 (FIVN), two key players in the enterprise cloud software industry, evaluating which stock offers a better investment opportunity. While Datadog excels in cloud monitoring and observability, Five9 focuses on cloud-based contact center infrastructure, both benefiting from the expanding enterprise software market. The analysis concludes that Five9 appears to be the better buy due to its predictable subscription revenues, focused contact center use case, and clearer AI-driven ROI, despite Datadog's premium valuation and usage-linked revenue model.

Traders have significantly increased their bearish bets on Five9 (NASDAQ:FIVN), purchasing 21,115 put options, a 361% increase over average volume. This unusual options activity coincides with notable insider selling, as CEO Michael Burkland and EVP Panos Kozanian recently offloaded significant shares. Despite a "Moderate Buy" consensus rating and a $50 million share buyback authorization, the surge in put options suggests a bearish sentiment among some investors.

This article compares Datadog (DDOG) and Five9 (FIVN), two key players in the enterprise cloud software industry, evaluating which stock presents a better investment opportunity. While Datadog specializes in cloud monitoring and observability, Five9 focuses on cloud-based contact center infrastructure. The analysis concludes that Five9 appears to be a better buy at current levels due to its predictable subscription revenues, focused contact center use case, and clearer AI-driven ROI, despite Datadog's higher growth projections and market performance.

Five9, Inc. has appointed Amit Mathradas as its new CEO, effective February 2, 2026, signaling a strong focus on AI-powered contact center solutions. Mathradas's extensive background in AI and scaling enterprise software is expected to reshape Five9's strategy and address competition in the AI market. Investors are keenly awaiting the 2026 investor day to understand how the new leadership will align AI product sets and partner ecosystems with financial targets for revenue growth, margins, and capital allocation.

Five9, Inc. (NASDAQ:FIVN) is currently trading at a low price-to-sales (P/S) ratio of 1.4x, significantly below the industry average for software companies. This valuation reflects investor concerns about its slower revenue growth compared to competitors, despite recent increases. Analysts predict Five9 will continue to underperform the industry in revenue growth, contributing to its suppressed share price.

Five9, Inc. has appointed Amit Mathradas as its new CEO, effective February 2, 2026, with the expectation that his AI-centric background will bolster the company's competitive stance in AI-powered contact center solutions. This leadership change is hoped to improve Five9's investment narrative, particularly as the company faces fierce competition and aims for durable, profitable growth despite slowing revenue guidance. Investors are keenly awaiting the 2026 investor day for details on Mathradas’s strategy to leverage AI and the partner ecosystem to enhance revenue growth, margins, and capital allocation.