Position Summary

The Senior Director, Product Management & Innovation owns the vision, strategy, roadmap, commercialization, and partner ecosystem for OSV's employee benefits and financial wellness portfolio. Operating within OSV's Product Operating Model, this leader grounds decisions in customer insight, market evidence, strategic alignment, and measurable outcomes rather than feature throughput.

The role partners closely with Sales, Marketing, Customer Success, Operations, Implementation, Engineering, Finance, Legal, Compliance, and Executive Leadership to create valuable, scalable offerings and bring them successfully to market.

Organization and Scope

• Initially leads one direct report, with the intention of hiring one additional team member as portfolio needs and growth warrant.
• Owns portfolio-level product strategy, investment recommendations, roadmap priorities, partner decisions, commercialization, and performance management.
• Leads through influence across the company and establishes clear decision rights with cross-functional stakeholders.

Portfolio Ownership

PORTFOLIO AREA

CURRENT AND FUTURE SCOPE

Financial wellness

Earned Wage Access; Workday Loans; future employee financial wellness offerings

Health and voluntary benefits

Customer Directed Health; Pet Insurance; employee-paid benefits; future voluntary benefit offerings

Payments and access

Digital Card and Wallet solutions; related payment and access experiences

Partner ecosystem

Benefits, financial services, lending, payments, wallet, and emerging employee wellness partners

Key Responsibilities
Product Strategy and Vision

• 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.

Customer Discovery and Market Insight

• 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.

Partner Strategy and Decisions

• 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.

Roadmap and Portfolio Management

• 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.

Commercialization and Lifecycle Leadership

• 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.

Product Performance and Business Outcomes

• 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.

People Leadership and Product Excellence

• 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.

Product Operating Model Expectations

PRINCIPLE

WHAT IT MEANS IN THIS ROLE

Outcomes over output

Success is measured by customer and business impact, not the number of features shipped.

Problems before solutions

The team develops deep understanding of customer needs and validates assumptions before committing investment.

Continuous discovery

Customer learning is an ongoing operating habit connected directly to product decisions.

Empowered decisions

The leader provides strategic context and clear boundaries, then enables the team to determine the best solutions.

Cross-functional partnership

Product, technology, operations, commercial, and risk partners work together from discovery through lifecycle management.

Evidence and learning

Roadmaps and investments are adjusted as new customer, market, product, and performance evidence emerges.

Qualifications
Required Experience and Capabilities

• 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.

Preferred Experience

• 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.

Leadership Competencies

COMPETENCY

WHAT GOOD LOOKS LIKE

Customer obsession

Builds deep understanding of employee, employer, buyer, and user needs.

Strategic clarity

Makes deliberate choices about target customers, problems, differentiation, partnerships, and investment.

Product judgment

Balances evidence, intuition, economics, risk, and learning to make sound product decisions.

Commercial acumen

Connects product value to positioning, adoption, revenue, scalability, and portfolio performance.

Partner leadership

Creates accountable relationships and makes objective decisions about partner fit and performance.

Influence and alignment

Builds trust, clarifies decisions, and aligns stakeholders across functional boundaries.

Systems thinking

Understands the connections among experience, technology, operations, partners, compliance, and economics.

Talent development

Creates clear ownership, coaches effectively, and builds capability as the team grows.

Measures of Success
First 12 Months

• A clear portfolio strategy, target customer definition, value propositions, strategic choices, and measurable outcomes are established and aligned.
• An evidence-based, multi-year roadmap and investment plan are in place.
• A repeatable partner evaluation framework, partner scorecards, and operating rhythms are implemented.
• Continuous discovery and customer insight practices are operating across the portfolio.
• Commercialization and stakeholder review practices are established for priority launches and lifecycle decisions.
• The existing team member has clear ownership and development objectives, and the timing and profile for the next hire are defined.

Ongoing

• Growth in appropriate measures of adoption, utilization, engagement, retention, satisfaction, and customer outcomes.
• Improvement in revenue contribution, portfolio economics, scalability, and return on product investment.
• Strong partner performance and timely decisions about expansion, remediation, renewal, or replacement.
• Higher-quality and faster product decisions supported by customer evidence and transparent tradeoffs.
• Consistent commercialization readiness and effective post-launch learning and optimization.
• A capable, accountable product team that operates with clear outcomes and appropriate autonomy.

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