Product Management Director – Workforce Engagement

Five9

Product Management Director leading intelligent workforce engagement solutions at Five9. Overseeing strategy and execution for AI-driven Workforce Engagement Management portfolio.

Posted 5/30/2026full-time🇺🇸 United StatesLead💰 $135,000 - $398,200 per yearWebsite

About the role

Key responsibilities & impact

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.

Requirements

What you’ll need

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.

Benefits

Comp & perks

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.

ATS Keywords

✓ Tailor your resume

Applicant Tracking System Keywords

Tip: use these terms in your resume and cover letter to boost ATS matches.

Hard Skills & Tools

B2B SaaS product managementWorkforce Engagement ManagementQuality ManagementWorkforce ManagementAI-driven Quality Managementworkforce forecastingmulti-skill schedulingintraday managementreal-time adherenceagentic AI architectures

Soft Skills

analytical skillsproblem-solving skillsbusiness acumencommunication skillsinfluencementoringinnovationcontinuous learningcollaborationcustomer feedback management

Certifications

Bachelor's degree in Computer ScienceBachelor's degree in EngineeringBachelor's degree in BusinessMBAadvanced degree