Head of Product and Strategy - Retirement & Wealth (Remote)
Product
Oak Brook, IL, USA
The Head of Product & Strategy will report to the President, Retirement & Wealth and serves as a key member of the R&W Executive Leadership Team (ELT). This role is responsible for defining and driving the end-to-end product and strategic agenda to accelerate growth, enhance client value and differentiate Inspira in the marketplace. Focus areas include; ownership of the product strategy and growth pipeline for Retirement & Wealth (R&W) - building the product roadmap, leading market and competitive analysis, and identifying organic and inorganic growth opportunities. The Head of Product & Strategy partners directly with the President and R&W leadership to turn strategy into an executable plan and serves as the primary leader on product and growth decisions for the business. This is a pivotal leadership role at a moment of transformation for Inspira, offering the opportunity to shape the future of our R&W business, drive meaningful growth, and build differentiated product capabilities.
Duties & Responsibilities:
- Owns the R&W product strategy and roadmap, prioritizing investment against market opportunity and client need
- Leads market sizing, competitive analysis, and strategic planning, translating findings into clear recommendations for the President and R&W leadership
- Builds and manages the R&W growth pipeline, including organic initiatives and M&A targets, partnering with Corporate Development on evaluation and due diligence
- Partners with Finance, Technology, and Operations leadership to align product strategy with R&W's operating model and resourcing
- Partners with finance on pricing and packaging strategies
- Leads through influence across Technology, Operations, Sales, Marketing, and Client Experience to align execution with product and strategic priorities
- Develops board- and leadership-level strategic materials and business cases
- Builds and scales innovation capabilities, including ideation, experimentation, and rapid testing
- Leads digital/product transformation initiatives to modernize the portfolio and client experience
- Defines and evolves the department’s operating model
- Builds and develops a high-performing team across product management and strategy
- Implements best-in-class product management practices, tools, and governance
- Other duties as assigned.
Accountabilities:
- Enterprise product strategy and roadmap prioritization
- Annual and multi-year strategic planning for R&W
- Product portfolio performance (revenue, adoption, margins)
- Build/buy/partner decisions
- Governance of product lifecycle (incubation → launch → optimization → sunset)
- Delivering product-led revenue growth and improving product-level profitability
- Finance partnership to define investment cases, ROI, and capital allocation across initiatives
- Engaging relationships directly with clients, partners, and the market to inform strategy and validate product direction
- Key representative of Inspira in industry forums and with key external stakeholders
Measures of Success:
- Revenue growth tied to product initiatives
- Client acquisition, retention, and engagement
- Speed to market / cycle time improvements
- Product adoption and utilization
- Portfolio ROI and margin improvement
- Innovation pipeline health