Chief Product & Strategy Officer (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

$215,000-$275,000 per year