Product Management Director – Workforce Engagement | JobSetuu

Description

Job Overview

• Source: Jobicy

Job Description

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

Expert Career Tips for Product Management Director – Workforce Engagement Roles

To succeed in a competitive market as a Product Management Director – Workforce Engagement, you need more than just technical skills. Here are some expert strategies to elevate your profile:

• Build a Strong Portfolio: For technical roles, a clean GitHub or a personal project site is essential. For non-technical roles, a case study portfolio demonstrating problem-solving and impact is equally valuable. Show, don't just tell, what you have achieved in your previous positions.
• Master the Narrative: When interviewing, use the STAR method (Situation, Task, Action, Result) to structure your answers. Quantify your results wherever possible—mentioning "increased efficiency by 20%" is much more impactful than saying "improved efficiency."
• Continuous Learning: The industry moves fast. Whether it's staying updated with the latest AI tools or mastering a new management methodology, continuous professional development is key. Consider obtaining industry-recognized certifications that align with Product Management Director – Workforce Engagement requirements.
• Networking: Connect with other professionals in similar roles. Join online communities, attend webinars, and engage in meaningful discussions on professional social networks. Often, the best opportunities come through referrals and community engagement.
• Soft Skills Matter: Communication, empathy, and leadership are often the deciding factors between two equally qualified technical candidates. Cultivate these skills as they are universally valued across all industries and seniority levels.

Additionally, research the specific company's culture and values. Tailoring your application to show how you align with their mission can significantly increase your chances of moving forward in the process.

Salary & Compensation

Salary not disclosed; typically competitive for the role.

Work Arrangement

Type: On-Site

Standard business hours at the office.

Comprehensive Application Strategy & Hiring Process

Applying for a new role is a marathon, not a sprint. Follow this strategic approach to maximize your success rate:

1. Initial Research & Tailoring

Don't send the same resume to every employer. Spend at least 30 minutes researching the company. Look for recent news, their product roadmap, and their team structure. Modify your summary and core competencies to reflect the specific keywords found in the job description.

2. The Perfect Cover Letter

If the application allows for a cover letter, use it to tell a story that your resume cannot. Explain why you are passionate about this specific company and how your unique background makes you the perfect fit for the challenges they are currently facing.

3. Navigating the Multi-Stage Interview

Most modern hiring processes involve 3-5 stages. This typically includes a recruiter screen, a technical or skill-based assessment, a peer interview, and a final leadership round. Prepare for each stage differently: focus on enthusiasm and fit for the recruiter, technical depth for the assessment, and strategic vision for the leadership round.

4. Post-Interview Follow-Up

Always send a personalized thank-you note within 24 hours of each interview. Reference a specific topic discussed during the call to demonstrate your active listening and genuine interest in the role.

By following these steps, you demonstrate a high level of professionalism and attention to detail that sets you apart from the average applicant.

Typical Interview Process

1. Resume screening
2. HR call
3. Skill interview
4. Final manager interview
5. Offer

Tip: Research the company's products and culture.

Global Market Intelligence & Relocation Insights

At JobSetuu, we specialize in helping talent navigate the global job market. Here is what you need to know about the current landscape in Global and beyond:

The demand for skilled professionals is increasingly borderless. For roles based in Global, understanding the local cost of living, visa requirements (if applicable), and cultural nuances is vital. If this is a remote role, consider the time zone alignment and the asynchronous communication culture of the hiring organization.

Relocation Support: Many forward-thinking companies offer relocation packages that include moving stipends, temporary housing, and legal assistance with work permits. When evaluating an offer, look beyond the base salary—consider the total compensation package, including equity, bonuses, and healthcare benefits.

Work-Life Balance Trends: Hybrid and remote work have become standard in many regions. Research the local labor laws and common practices regarding work hours and vacation time to ensure the role aligns with your lifestyle goals.

Leveraging JobSetuu's tools can help you compare salaries across different cities and understand the "purchasing power" of your potential offer, ensuring you make an informed decision for your long-term career path.

Skills & Competency Roadmap for Professional Development

To remain competitive in Professional Development, we recommend focusing on the following core competencies over the next 12-18 months:

• Technical Mastery: Deepen your expertise in the core tools and languages relevant to your field. For developers, this might be cloud architecture; for marketers, it might be data-driven attribution modeling.
• AI Augmentation: Learn how to leverage generative AI and automation tools to increase your productivity. Understanding how to integrate these technologies into your workflow is becoming a non-negotiable skill.
• Leadership & Strategy: Even in individual contributor roles, the ability to think strategically and lead projects from inception to completion is highly valued. Focus on stakeholder management and high-level project planning.
• Data Literacy: The ability to interpret data and use it to drive decisions is essential across all business functions. Familiarize yourself with data visualization and basic analytical concepts.

By investing in these areas, you not only prepare yourself for the role you are applying for today but also build a resilient foundation for the opportunities of tomorrow.

Apply via JobSetuu

Discover your next career milestone on JobSetuu. This Product Management Director – Workforce Engagement position is part of our commitment to bringing you the most relevant and high-impact job openings globally. At JobSetuu, we simplify your job search by aggregating premier listings and providing the tools you need to stand out. Don't miss the chance to elevate your professional journey—explore more opportunities and career insights on our platform today.