Head of Product and Strategy - Retirement & Wealth (Remote)

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 Minimum required: 15+ years of experience in strategy, product leadership, or strategy consulting required Bachelor’s degree in Business, Finance, Economics, or a related field or equivalent combination of education, experience and training required Experience scaling product organizations in growth or transformation environments Track record of driving measurable commercial outcomes (not just delivery) Experience integrating strategy and execution Background in regulated or financial services (if applicable) Ability to operate at ELT / board level Additional preferred: Experience in financial services, retirement, or benefits preferred Experience building or leading a product or corporate strategy function preferred Experience supporting M&A pipeline development, including deal evaluation and due diligence, preferred MBA preferred Skills & Abilities: Strong financial modeling and business case development skills Ability to translate market and competitive analysis into clear, actionable strategic recommendations Strong executive presence; experienced advising and presenting to President- or C-suite-level leadership Strong project management skills, including the ability to coordinate cross-functional initiatives Comfortable operating with ambiguity and building a function in a still-forming organization Strong written and verbal communication skills Other Requirements: Typical schedule is Monday–Friday, with the flexibility to work evenings or weekends as needed to support board meetings, leadership sessions, or deal timelines Employees within a 90-minute radius of our Oak Brook, IL headquarters are required to adhere to Company in-office work guidelines of 4 days per month minimum from 10 am to 2 pm CT (1 of the 4 days must be a Monday or Friday) Occasional travel (up to 20%) for leadership meetings, board sessions, and industry events Ability to provide personal transportation for training or meetings may be required Occasionally lifts up to 25 pounds Prolonged periods of sitting and operating standard office equipment