Head of Product and Strategy - Retirement & Wealth; Remote

Join Us! Take the next step in your journey at Inspira Financial. Guided by our mission to enable better health and greater wealth, we help businesses and individuals thrive today, tomorrow, and into retirement by strengthening and simplifying the health and wealth journey.

Our values shape how we show up every day. Lead with Heart by acting with compassion, empathy, and doing what's right;
Cultivate Trust through integrity, transparency, and accountability;
Aim Higher by never settling for what's expected and continually raising the standard; and Win Together by collaborating inclusively to achieve the best outcomes.

Join us on our journey as we work together to take on the complex and the everyday--turning collective effort into life‑changing impact that enriches lives and helps build a better future. Learn more at

We believe in finding the best talent! While some roles are based at one of our office locations, remote roles can sit in any of the following states: AL, AZ, FL, GA, IA, IL, IN, MI, MN, MO, NC, NE, PA, SC, TN, TX, UT, VA and WV. Remote status and role locations are subject to change. Relocation is not provided.

Employees within a 90-minute radius of our Oak Brook, IL headquarters are required to adhere to the company in‑office work guidelines of 4 days per month minimum from 10 am to 2 pm (1 of the 4 days must be a Monday or Friday). This requirement does not apply to support specialist positions.

Don’t meet every single requirement? That's okay. At Inspira Financial, we know growth comes from people who are willing to learn, challenge themselves, and aim higher. We value individuals who lead with heart, cultivate trust, and collaborate to win together. If you're energized by meaningful work, continuous development, and being part of a team that turns collective effort into real impact, Inspira Financial could be the right next step in your journey.

We look forward to receiving your application.

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.

• 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…