Amit Mathradas and the Era of Outcome-Based CX with Five9

The arrival of Amit Mathradas as CEO of Five9 on February 2, 2026, marks more than just a leadership change; it signals a fundamental shift in how the industry values Customer Experience (CX) technology. Having followed Amit’s career through our shared history at Web.com—where I was part of the Network Solutions acquisition—I have seen his ability to navigate complex enterprise environments firsthand. His global experience at PayPal, Dell, and Avalara—where he grew the business from $300M to $1B—reinforces a pedigree built for high-scale automation (Yahoo Finance).

This leadership transition comes at a time of strength for the company. Mike Burkland, who has navigated ongoing health challenges, remains a vital force as Executive Chairman, allowing him to focus on his well-being while ensuring strategic continuity (CX Today). Under his guidance, Five9 reached a milestone $1.15 billion in 2025 revenue (a 10% year-over-year increase), exiting the year with a $1.2 billion run rate (Yahoo Finance).

The Founding Journey: From Reliability to Intelligence

Founded in 2001, Five9’s name was a direct promise of 99.999% uptime—the gold standard for telecommunications reliability. What began as a mission to democratize call center software for SMBs by replacing on-premise hardware has evolved into an "AI-native" Intelligent CX Platform. Through the strategic acquisitions of Whendu and SoCoCare, Five9 bolstered its digital and automation capabilities, moving from a standard dialer to a sophisticated orchestration engine.

Vertical Strengths: Where Five9 Wins

Five9’s strength lies in highly regulated, complex enterprise environments. Their primary verticals demonstrate where deep integration and ROI meet:

Financial Services: Handling high-security transactions and complex advisory workflows with automated compliance logging.
Healthcare: Managing patient engagement through HIPAA-compliant AI suites and deep integration with healthcare-specific CRMs.
Retail: Managing seasonal spikes with "Agentic AI" that handles logistics, returns, and inventory queries without human intervention.

The AI Bedrock: From $100M to Enterprise Scale

There is a prevailing narrative that AI in the contact center began with the rise of Large Language Models in late 2022. However, for Five9, machine learning has been a core component for years. A concrete proof point of this "bedrock" thesis is the company's Enterprise AI annual run-rate revenue, which surpassed $100 million in Q4 2025 (Yahoo Finance).

This early adoption allowed the company to move past experimental pilots. By the end of 2025, Five9 achieved annual GAAP profitability for the first time, reporting GAAP EPS of $0.45 per diluted share (Five9).

The Mathradas Mandate: Outcome-Based CX

At Nintex and Avalara, Amit pioneered high-growth business orchestration. This experience is critical as Five9 rolls out its Agentic Quality Management (AQM) and "Genius AI." The goal is no longer just assisting a human agent, but enabling autonomous workflows that can review 100% of customer interactions. As Amit takes the helm, we are seeing the "Mathradas Era" focus on ROI and predictable expenses—key drivers for executive leadership today.

Strategic Shift: The 5-Year Outlook

The next five years will be defined by Platform Consolidation. Five9 has initiated 2026 revenue guidance with a midpoint of $1.254 billion, with management projecting a return to double-digit revenue growth in the second half of the year (Yahoo Finance). The strategy will likely focus on three pillars:

Outcome-Based Pricing: As AI agents handle a higher percentage of support, the traditional "per-seat" revenue model will evolve toward "per-resolution" billing.
Native AI Embedding: Moving away from third-party wrappers to deeply integrated models that prioritize data security and reduced latency.
Assistance over Replacement: Ensuring software assists human agents with real-time intelligence while delegating routine "agentic" tasks to AI bots.

Shashi's Take

There is a lot of opportunity for growth in CX, but ROI and predictable expenses remain the key. Companies have to make their software assist, not replace, the human element of the workforce. Looking forward to following Five9 more closely since Amit is on board—our shared history at Web.com reminds me that technical transitions only succeed when they simplify the user journey.

Works Cited

Five9. "Five9 Reports Record Full Year 2025 Revenue of $1.15 Billion." 19 Feb. 2026, https://investors.five9.com/news-releases/news-release-details/five9-reports-record-full-year-2025-revenue-115-billion.

Yahoo Finance. "Five9 (FIVN) Q4 2025 Earnings Call Transcript and CEO Transition." 19 Feb. 2026, https://finance.yahoo.com/news/five9-names-amit-mathradas-ceo-130000456.html.

CX Today. "Five9 Leadership: Mike Burkland and the Future of CX." Feb. 2026, https://www.cxtoday.com/.

Disclaimer: This blog reflects my personal views only. AI tools may have been used for research support. This content does not represent the views of my employer, Info-Tech Research Group.