Product Management Director – Workforce Engagement

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 details when needed

Go-to-Market & Business Impact

• Develop compelling product positioning, packaging, and pricing strategies that highlight Five9’s differentiated WEM capabilities across both QM and WFM
• Partner closely with customers, system integrators, and partners to gather insights, validate solutions, and drive measurable business outcomes
• Lead beta programs and customer pilots across QM and WFM, managing feedback loops and iterating rapidly based on real-world usage
• Build business cases and ROI models that demonstrate the value of Five9’s integrated workforce engagement solutions

Thought Leadership & Collaboration

• Champion best practices in WEM product development across the organization, including responsible AI principles, agentic AI evaluation frameworks, and user-centered design
• Foster a culture of innovation, experimentation, and continuous learning within the product organization
• Mentor and influence associate product managers and cross-functional peers, elevating the team’s capabilities in AI/ML, quality management, and workforce management domain knowledge

What You Bring

Required Qualifications

• Bachelor’s degree in Computer Science, Engineering, Business, or related field; MBA or advanced degree is a strong plus
• 9+ years of experience in B2B SaaS product management, with significant focus on Workforce Engagement Management, Quality Management, or Workforce Management products
• Hands-on experience designing and building WFM solutions, including core capabilities such as forecasting, scheduling, intraday management, and real-time adherence
• Hands-on experience designing and building AI-driven QM solutions, including automated interaction evaluation, scoring, and coaching workflows
• Working knowledge of agentic AI architectures, including autonomous agents with planning, reasoning, tool use, and learning capabilities, with demonstrated experience applying these in a product context
• Deep understanding of contact center operations, the workforce planning lifecycle, and quality assurance frameworks — from long-term capacity planning through real-time floor management and interaction evaluation
• Proven track record of successfully launching and scaling WEM, WFM, or QM products from conception through growth
• Exceptional analytical and problem-solving skills, with demonstrated ability to make data-driven decisions in ambiguous situations
• Strong business acumen with experience in product positioning, pricing, and go-to-market strategy
• Outstanding communication skills, able to influence senior stakeholders and translate complex operational and technical concepts for diverse audiences
• Experience leading through influence in matrixed, global organizations with distributed teams
• Track record of managing beta programs, running experiments, and leveraging customer feedback to drive product iterations

Preferred Qualifications

• Deep domain expertise in Workforce Engagement Management platforms (e.g., NICE, Verint, Aspect, Calabrio, Genesys) with a strong understanding of competitive dynamics across both QM and WFM
• Hands-on experience designing and building agentic AI platforms, including autonomous agents with planning, reasoning, and learning capabilities applied to quality management or workforce optimization use cases
• Experience with agentic AI design patterns such as ReAct, Chain-of-Thought, tool use, and multi-agent orchestration, and knowledge of LLM applications, prompt engineering, and RAG architectures
• Experience integrating AI and machine learning into WFM workflows, including AI-driven forecasting, automated scheduling optimization, and intelligent adherence management
• Experience with forward deployment models, working directly with customers during implementation, onboarding, and optimization phases to drive adoption and value realization
• Strong understanding of contact center quality frameworks (COPC, Six Sigma, Lean) and how QM and WFM intersect within broader workforce optimization strategies
• Knowledge of AI evaluation methodologies: quality scoring, hallucination detection, bias assessment, performance monitoring, and continuous improvement
• Familiarity with omnichannel contact center environments and the complexity of multi-skill, multi-channel workforce planning and quality evaluation
• Knowledge of cloud-based WEM architectures and modern API-driven integrations with ACD, CRM, and HR systems
• Background working in fast-paced, high-growth SaaS companies serving enterprise customers
• Previous experience managing products in global, distributed teams across multiple time zones