[Remote] Product Management Director – Workforce Engagement

Note: The job is a remote job and is open to candidates in USA. Five9 is a leading provider of cloud contact center software, bringing the power of cloud innovation to customers worldwide. They are seeking a Product Management Director - Workforce Engagement to lead the future of intelligent workforce engagement, shaping the strategy and execution of their Workforce Engagement Management portfolio, which includes AI-driven Quality Management and Workforce Management. This role involves defining product vision, collaborating with cross-functional teams, and driving product development to optimize contact center operations.

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

Skills

• 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
• 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

Benefits

• Annual performance bonus
• Stock
• Other applicable incentive compensation plans
• 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

Company Overview

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