Sr. Director, Product Management & Innovation

OneSource Virtual delivers technology and expert services that automate payroll, tax, financial, and benefits-related administrative tasks for Workday customers. The Senior Director, Product Management & Innovation will own the vision, strategy, roadmap, commercialization, performance, and partner ecosystem for the company’s employee benefits and financial wellness portfolio while leading cross-functional initiatives and a growing product team.

Responsibilities:

• Define and continuously evolve the portfolio vision and strategy, including target customers, priority needs, differentiated value propositions, strategic choices, and measures of success
• Translate company strategy into product outcomes, portfolio priorities, investment recommendations, and a coherent multi-year direction
• Assess market trends, competitive dynamics, economics, regulatory considerations, and adjacent opportunities to inform strategic choices
• Create clear product narratives that align executives and cross-functional teams around where OSV will play and how the portfolio will win
• Establish continuous discovery practices that maintain direct, regular contact with employers, employees, buyers, users, and internal customer-facing teams
• Frame customer problems and opportunities before prescribing solutions; validate assumptions through interviews, data, research, prototypes, and market tests
• Connect discovery insights to strategy, roadmap choices, partner decisions, and product improvements
• Build shared visibility into customer evidence so prioritization is grounded in learning rather than stakeholder volume
• Define the partner ecosystem strategy and determine where OSV should build, buy, integrate, or partner
• Lead partner evaluation and selection using clear criteria for customer value, strategic fit, economics, capabilities, scalability, experience, risk, and operational readiness
• Partner with Legal, Compliance, Finance, Technology, Security, and Operations on due diligence, contracting, integration, and launch decisions
• Establish partner scorecards, operating rhythms, and stakeholder reviews to manage performance, resolve issues, and guide renewal, expansion, or replacement decisions
• Own an outcome-based roadmap that communicates priority problems, intended outcomes, strategic bets, dependencies, and learning milestones
• Prioritize across the portfolio by balancing customer value, business impact, confidence, effort, risk, and organizational capacity
• Lead quarterly and annual planning for the portfolio and provide transparent rationale for tradeoffs and sequencing
• Ensure teams have sufficient context and decision clarity to solve problems without becoming feature-order takers
• Partner across Marketing, Sales, Customer Success, Implementation, Operations, Support, Finance, and Compliance to shape commercialization from the beginning of product work
• Define target segments, positioning, packaging, pricing inputs, channel approach, launch objectives, enablement needs, operational readiness, and adoption plans
• Use stakeholder reviews to align on readiness, unresolved risks, decisions, ownership, and next steps without creating unnecessary approval bureaucracy
• Monitor post-launch adoption, engagement, customer feedback, service performance, economics, and partner results; adjust the product and go-to-market approach based on evidence
• Manage products across their lifecycle, including scaling, optimization, repositioning, consolidation, and retirement recommendations
• Define a balanced scorecard of customer, product, partner, operational, commercial, and financial outcomes
• Monitor adoption, utilization, engagement, retention, satisfaction, revenue contribution, cost-to-serve, partner performance, and portfolio return
• Create concise executive reporting that highlights outcomes, learning, decisions, risks, and recommended actions
• Treat roadmap and investment decisions as hypotheses to be measured and refined rather than commitments to output
• Lead, coach, and develop the initial team member and hire an additional team member as the portfolio expands
• Set clear outcomes, decision rights, expectations, and development plans while creating meaningful ownership for each team member
• Build team capability in product discovery, strategy, partner management, roadmapping, analytics, experimentation, and commercialization
• Model customer obsession, intellectual honesty, accountability, collaboration, and continuous learning

Requirements:

• 8+ years of progressive experience in product management, product strategy, employee benefits, fintech, HR technology, payments, lending, or a related field
• Demonstrated ownership of product strategy, roadmaps, portfolio choices, and measurable product or business outcomes
• Experience evaluating, selecting, negotiating with, and managing external product or technology partners
• Strong commercial and financial acumen, including the ability to assess market attractiveness, customer value, business cases, economics, and investment tradeoffs
• Experience leading complex, cross-functional initiatives and influencing senior stakeholders without relying solely on formal authority
• Strong analytical, communication, and executive presentation skills
• People leadership or coaching experience, with the ability to build a small, high-impact product team
• Employee benefits, voluntary benefits, financial wellness, consumer finance, lending, payments, or digital wallet experience
• Experience with SaaS, partner-led, platform, marketplace, or ecosystem business models
• Knowledge of the Workday ecosystem and employer-sponsored employee experiences
• Experience operating in regulated environments and partnering with Legal, Compliance, Security, and Risk teams