Product Management Director – Workforce Engagement

Product Management Director – Workforce Engagement

Join Five9, a leading provider of cloud contact center software, and help us bring joy to customer experiences worldwide. We foster a team-first culture that celebrates diversity and empowers employees to be their authentic selves, driving innovation, growth, and a shared journey of success.

About the Role

Five9 is seeking a visionary Product Management Director to lead the future of intelligent workforce engagement. This is a critical individual contributor role for a seasoned product leader passionate about deep domain ownership, hands-on execution, and strategic influence. You will shape the strategy and execution of Five9's Workforce Engagement Management (WEM) portfolio, including AI-driven Quality Management (QM) and Workforce Management (WFM). Your work will transform how contact centers evaluate interactions, optimize agent performance, forecast demand, and manage their workforce at scale, positioning Five9 as a leader in intelligent workforce engagement.

Key Responsibilities

Strategic Leadership

• Define and drive the end-to-end product vision and strategy for Five9's WEM portfolio (AI-driven QM and WFM).
• Own the product roadmap, balancing innovation, customer needs, competitive positioning, and technical feasibility.
• Serve as the internal and external thought leader on WEM, agentic AI in quality management, and intelligent workforce optimization.
• Conduct deep competitive and market analysis to identify emerging trends in automated quality management, agentic AI, and workforce planning.

Product Development & Execution

• Partner cross-functionally with engineering, design, data science, and go-to-market teams to translate strategy into innovative QM and WFM capabilities.
• Design and oversee the development of AI-driven QM capabilities, including autonomous AI agents for interaction evaluation, pattern recognition, root cause analysis, and coaching recommendations.
• Design and oversee the development of core WFM capabilities, including forecasting, multi-skill scheduling, intraday management, real-time adherence, and performance analytics.
• Define detailed product requirements for complex agentic and WFM systems, leveraging hands-on experience.
• Drive deployment engagements with enterprise customers, optimizing AI agent performance and WFM adoption.
• Balance high-level strategic thinking with tactical execution, diving deep into technical and operational details.

Go-to-Market & Business Impact

• Develop compelling product positioning, packaging, and pricing strategies.
• Partner closely with customers, system integrators, and partners to gather insights and drive measurable business outcomes.
• Lead beta programs and customer pilots, managing feedback loops for rapid iteration.
• Build business cases and ROI models demonstrating the value of Five9's integrated workforce engagement solutions.

Thought Leadership & Collaboration

• Champion best practices in WEM product development, including responsible AI principles and user-centered design.
• Foster a culture of innovation, experimentation, and continuous learning.
• Mentor and influence associate product managers and cross-functional peers.

Requirements

Required Qualifications

• Bachelor's degree in Computer Science, Engineering, Business, or related field (MBA or advanced degree a plus).
• 9+ years of experience in B2B SaaS product management, with a significant focus on WEM, QM, or WFM products.
• Hands-on experience designing and building WFM solutions (forecasting, scheduling, intraday management, real-time adherence).
• Hands-on experience designing and building AI-driven QM solutions (automated interaction evaluation, scoring, coaching).
• Working knowledge of agentic AI architectures and demonstrated experience applying them in a product context.
• Deep understanding of contact center operations, workforce planning, and quality assurance frameworks.
• Proven track record of successfully launching and scaling WEM, WFM, or QM products.
• Exceptional analytical and problem-solving skills with data-driven decision-making abilities.
• Strong business acumen in product positioning, pricing, and go-to-market strategy.
• Outstanding communication skills, with the ability to influence senior stakeholders.
• Experience leading through influence in matrixed, global organizations.
• Track record of managing beta programs and leveraging customer feedback for product iteration.

Preferred Qualifications

• Deep domain expertise in WEM platforms (e.g., NICE, Verint, Calabrio) and competitive dynamics.
• Hands-on experience designing and building agentic AI platforms for WEM use cases.
• Experience with agentic AI design patterns (e.g., ReAct, Chain-of-Thought) and LLM applications.
• Experience integrating AI/ML into WFM workflows.
• Experience with forward deployment models and direct customer engagement.
• Strong understanding of contact center quality frameworks (COPC, Six Sigma).
• Knowledge of AI evaluation methodologies.
• Familiarity with omnichannel contact center environments.