Product Management Director – Workforce Engagement

Join us in bringing joy to customer experience. Five9 is a leading provider of cloud contact center software, bringing the power of cloud innovation to customers worldwide. Living our values everyday results in our team-first culture and enables us to innovate, grow, and thrive while enjoying the journey together. We celebrate diversity and foster an inclusive environment, empowering our employees to be their authentic selves. We are seeking a Product Management Director - Workforce Engagement to lead the future of intelligent workforce engagement at Five9. This is an individual contributor (IC) role for a seasoned product leader who thrives in deep domain ownership, hands-on execution, and strategic influence without direct reports. In this pivotal role, you will shape the strategy and execution of Five9's Workforce Engagement Management (WEM) portfolio — spanning AI-driven Quality Management (QM) and Workforce Management (WFM) — transforming how contact centers evaluate interactions, optimize agent performance, forecast demand, and manage their workforce at scale. You will position Five9 as a leader in intelligent workforce engagement, delivering products that fundamentally change how organizations plan, manage, and continuously improve their contact center operations. We're looking for a visionary product leader who combines deep WEM domain expertise with hands-on experience in agentic AI, exceptional strategic thinking, and cross-functional influence. The ideal candidate brings a proven track record in QM and WFM product management, hands-on experience designing and building workforce engagement solutions, and a passion for solving complex operational problems through intelligent automation and autonomous AI agents. You should be equally comfortable discussing agentic AI architectures, forecasting algorithms, and scheduling optimization with engineers as you are presenting strategic roadmaps to executive leadership. You will collaborate with a global team spanning the United States, Portugal, and India. What You'll Do Strategic Leadership Define and drive the end-to-end product vision and strategy for Five9's Workforce Engagement portfolio — encompassing AI-driven Quality Management and Workforce Management — aligning with company objectives and market opportunities Own the product roadmap across QM and WFM, balancing innovation with customer needs, competitive positioning, and technical feasibility Serve as the internal and external thought leader on WEM, agentic AI applications in quality management, and intelligent workforce optimization, representing Five9 at industry events and with key customers Conduct deep competitive and market analysis, identifying emerging trends in automated quality management, agentic AI, workforce planning, and contact center optimization technologies Product Development & Execution Partner cross-functionally with engineering, design, data science, and GTM teams to translate strategy into innovative QM and WFM capabilities Design and oversee the development of AI-driven Quality Management capabilities, including autonomous AI agents that perform interaction evaluation, pattern recognition, root cause analysis, coaching recommendations, and continuous improvement Design and oversee the development of core WFM capabilities including workforce forecasting, multi-skill scheduling, intraday management, real-time adherence, and performance analytics Define detailed product requirements for complex agentic and WFM systems, including agent planning, tool use, decision-making logic, learning mechanisms, and scheduling optimization engines — drawing on firsthand experience building or significantly evolving these platforms Drive forward deployment engagements with enterprise customers, working hands-on to optimize AI agent performance, WFM adoption, and overall workforce engagement outcomes Balance high-level strategic thinking with tactical execution, diving deep into technical and operational detail…