Sr. Director, Product Management & Innovation

OSV

1d • Remote

About The Position

OneSource Virtual (OSV) has worked exclusively with Workday customers since 2008 to deliver compliant, in-tenant technology and expert services to automate the administrative, transactional tasks of payroll, taxes, earned wage access, accounts payable, and benefits. With over 1,500 customers, 92% retention, and $225+ billion in treasury movement annually, OSV helps organizations maximize their Workday investment and operate it with confidence. Payroll, benefits, and finance solutions — all in one place. 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.

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.

Nice To Haves

• 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.

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.

Benefits

• You are encouraged to learn and share ideas when you join the OneSource Virtual team.
• We reward innovative thinking, fresh perspectives, creative collaboration, and hard work.
• As an organization experiencing routine strategic growth, we are always looking for intelligent, talented, and forward-thinking professionals to join our team.
• OSV employees enjoy a values-based culture, upward mobility, and professional development with opportunities of all kinds.

What This Job Offers

• Job Type: Full-time
• Career Level: Director
• Education Level: No Education Listed