Product Management Director – Workforce Engagement

Five9•San Ramon, CA

7h•$135,000 - $398,200•Hybrid

About The Position

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.

Requirements

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

Nice To Haves

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

Responsibilities

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
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
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
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

Benefits

Health, dental, and vision coverage, beginning on the first day of employment. Five9 covers 100% of the employee portion of the health, dental and vision coverage and shares a high portion of the dependent cost.
Short & Long-Term Disability
Basic Life Insurance
401k saving plan with employer matching
Access to an innovative mental health support platform that offers personalized care and resources in areas such as: therapy, coaching and self-guided mindfulness exercises for all covered employees and their covered dependents.
Generous employee stock purchase plan.
Paid Time Off
Company paid holidays
Paid volunteer hours
12 weeks paid parental leave.