Inspira Financial provides health, wealth, retirement, and benefits solutions that strengthen and simplify the health and wealth journey. With more than 7 million clients, representing over $62 billion in assets, Inspira works with thousands of employers, plan sponsors, recordkeepers, TPAs, and other institutional partners — helping the people they care about plan, save, and invest for a brighter future. Inspira relentlessly pursues better outcomes for all with our automatic rollover services, health savings accounts, emergency savings funds, custody services, and more. Learn more at inspirafinancial.com.
Head of Product and Strategy - Retirement & Wealth (Remote)
Location
Illinois
Posted
1 day ago
Salary
$215K - $275K / year
Seniority
Lead
Job Description
Head of Product and Strategy - Retirement & Wealth (Remote)
Inspira Financial
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. We 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 inspirafinancial.com. 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. Inspira Financial provides health, wealth, retirement, and benefits solutions that strengthen and simplify the health and wealth journey. With more than 7 million clients, representing over $62 billion in assets, Inspira works with thousands of employers, plan sponsors, recordkeepers, TPAs, and other institutional partners -- helping the people they care about plan, save, and invest for a brighter future. Inspira relentlessly pursues better outcomes for all with our automatic rollover services, health savings accounts, emergency savings funds, custody services, and more. Learn more at inspirafinancial.com . We have been recognized for our remarkable growth on lists such as Crain's Fast 50 and Inc. 5000, and for our outstanding workplace culture and benefits with Built In's 2025 Best Places to Work and Gallagher's 2022 Best-In-Class Employer awards. Job Summary & Responsibilities 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 Preferred Qualifications 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 Compensation & Benefits $215,000-$275,000 per year
Related Guides
Related Categories
Related Job Pages
More Strategy Jobs
Director, Web & Digital Strategy
JitterbitAward-winning low-code automation solutions and services to accelerate the digital journey. Work happier, not harder.
• Oversee the overall strategy for web and related digital properties, particularly for key audiences including customers, prospects, partners, etc. • Implement strategies to map and grow key web KPIs, including traffic, sessions, lead conversion, SEO, AIO/GEO, etc. • Collaborate cross-functionally with internal leaders across sales, product, support and engineering teams • Manage multiple and/or concurrent creative, web and digital agencies • Drive web strategies as it relates to marketing campaigns, business announcements, product launches, competitive takeouts, etc. • Have overall responsibility of the website’s content, presentation and usability in addition to overall administration of content management system (CMS) processes and technology • Manage project-planning processes (e.g., timelines, sprint planning, milestone tracking) in an agile environment or similar • Ability to do some light hands-on development and content entry within the CMS
Strategic Advisor
Engage fiGuiding banks and credit unions through their strategic processes with a focus on long-term relevance.
• Prospecting, qualifying, and closing new sales opportunities across the country for our consulting lines of business • Guides credit unions and banks in evaluating and selecting vendors based on their strategic goals • Establishes executive relationships with financial institutions across the country and sells Payments-related products (Credit, Debit, PIN Networks, Loyalty), Digital/Mobile Banking, Core Processing, and any related ancillary services • Develops new business via cold calling, email, and social media • Generates leads by attending industry events (tradeshows) • Conducts industry webinars educating the market on our services • Establishes executive level relationships with credit unions and banks of all sizes • Conducts needs analysis to identify a bank’s challenges and align with engage fi services • Works closely with marketing resources to leverage marketing campaigns • Manages all sales activity in the internal CRM system for reporting • Facilitates creative problem-solving sessions with all levels of leadership teams across different lines of business disciplines • Presents complex solutions to senior leadership teams
Accounting Industry Strategy Expert
SweetRushAt SweetRush, we believe that when you put people at the center of business, magic happens. As a global leader in learning and development, we blend high-end storytelling, emerging tech like AI and VR, and deep psychological insights to help organizations—from iconic global brands to essential nonprofits—flourish. We are a remote-first, tight-knit community built on a foundation of radical empathy and creative excellence.
Role Description SweetRush has an exciting opportunity for a talented professional to join our Custom Learning team for a short-term engagement as a Subject Matter Expert in the Accounting industry. We are looking for a forward-thinking Accounting Industry Strategy expert to help shape an innovative, commercial B2B learning solution designed for the accounting profession. This solution empowers early-career CPAs through immersive, tech-enabled training. You will be a key collaborative partner in ensuring this product addresses the massive talent readiness and retention challenges facing accounting firms today. - Participate in dynamic virtual CoDesign sessions alongside SweetRush’s Learning Experience Design, Creative, and Engineering teams, and client stakeholders. - Ideate simulated and AI-driven experiences that accounting firms will view as required training for their staff. Qualifications - A seasoned industry veteran within public accounting who understands the operational and talent challenges of managing junior staff. - Ability to represent both tax and audit at the entry- to senior-staff level. - Passionate about the evolution of the profession and enthusiastic about cutting-edge learning tech (AI, simulations). - Comfortable brainstorming in a high-energy, ambiguous, and collaborative environment. - Excellent communication skills with the ability to influence and align with executive-level stakeholders. - CPA preferred but not required. Requirements - Contract Type: Freelance - 1099. - Project Duration: 11 weeks. - Project Capacity: Up to 3 hours per week. - Hourly Range: $125/hour. - Approximate Time Commitment: ~25-30 hours spread across multiple weeks. - Up to seven (7) virtual CoDesign sessions ranging from 2-3 hours. - 30-minute debrief sessions with SweetRush after each CoDesign session. - Participation in developing a Proof of Concept. Benefits - Remote work flexibility. - Opportunity to collaborate with a talented team. - Engagement in innovative projects. Company Description At SweetRush, we believe that when you put people at the center of business, magic happens. As a global leader in learning and development, we blend high-end storytelling, emerging tech like AI and VR, and deep psychological insights to help organizations flourish. - Remote-first, tight-knit community built on a foundation of radical empathy and creative excellence. - Work with incredible partners such as Hilton, Google, Bridgestone, Adidas, and SHRM. - Commitment to spreading good in the world while balancing profit.
Underwriting Strategy and Process Manager
Farmers InsuranceHeadquartered in Woodland Hills, California, Farmers Insurance is a leading insurance group offering a variety of policies for individuals and small businesses.
Title: Underwriting Strategy & Process Manager Location: Los Angeles United States Job Description: 35027 We are Farmers – where ambition meets opportunity. At Farmers, we’re not just known for unforgettable jingle – we’re a team with a passion for purpose and making a real difference in people’s lives. We deliver peace of mind when it matters most. Our results-driven, high-performance culture thrives on creativity, accountability and bold solutions. Here, growth isn’t just a goal – it’s a way of life for both the organization and every individual on our team. We tackle challenges head-on, learn from every experience and measure our impact on the customers who trust us. Join an award-winning, equal opportunity employer, where you’ll find more than a job – you’ll find a supportive community. Enjoy competitive benefits, take part in meaningful volunteer projects, and help shape the future alongside talented colleagues across all backgrounds. At Farmers, helping others is at the heart of what we do. Workplace: Hybrid ( #LI-Hybrid ), Remote ( #LI-Remote ) Farmers believes in a culture of collaboration, creativity, and innovation, which thrives when we have the ability to work flexibly in a virtual setting as well as the opportunity to be together in person. Our hybrid work environment combines the best of both worlds with at least three (3) days in office and up to two (2) days virtual for employees who live within fifty (50) miles of a Farmers corporate office. Applicants beyond fifty (50) miles may still be considered. Job Summary Leads underwriting strategy, operational excellence, business process design, and technology enablement initiatives across Commercial Property, Casualty, Auto, and Workers Compensation lines of business. Partners with Underwriting, Product, Technology, Analytics, Operations, and Go-To-Market teams to develop underwriting capabilities, implement strategic initiatives, govern underwriting rules and decision-support tools, and drive profitable growth through process improvement, modernization, and data-driven solutions. Essential Job Functions · Serves as the underwriting business lead for strategic initiatives, product launches, system conversions, automation initiatives, workflow enhancements, and platform modernization efforts. · Establishes and maintains governance processes for underwriting eligibility, appetite, referral, and automation rules; evaluates proposed rule changes for operational, customer, and profitability impacts. · Acts as a liaison between Home Office Underwriting, Commercial Underwriting Centers, IT, Product Platform Development, Product Development, State Pricing, and Forms teams. · Evaluates corporate policies, guidelines, processes, and procedures related to Commercial Underwriting operations and recommends and directs modifications and enhancements. · Develops and maintains underwriting resources, decision-support tools, operational documentation, and knowledge repositories that improve consistency, efficiency, and underwriting effectiveness. · Develops and oversees commercial underwriting tools and guidelines for production teams, post validation teams, QA, and loss control. · Develops, oversees, and leverages reporting, analytics, dashboards, and operational metrics to identify trends, measure initiative success, and support underwriting decision-making. · Evaluates, implements, and governs internal and external data sources used in underwriting, risk selection, validation, and straight-through processing initiatives. · Serves as a technical underwriting consultant to Home Office and Commercial Center leadership, providing guidance on risk selection, underwriting practices, operational challenges, and strategic initiatives. · Performs and directs special projects, industry research and development, and training enhancements; develops, implements, and monitors third-party validation programs. · Provides support for training and management of the risk selection process and recommends corrective action. · Facilitates knowledge-sharing initiatives and promotes continuous learning related to underwriting trends, emerging risks, industry developments, and critical thinking in underwriting decision-making. Education Requirements · High school diploma or equivalent required. · Bachelor’s degree preferred, preferably in a business-related field of study. · Completion of or actively pursuing CPCU or other relevant insurance designation preferred. Experience Requirements · Seven years of Commercial Underwriting experience in property/casualty, auto, and/or Workers Compensation lines of business, preferably including supervisory/management experience · Two years Management experience as a Commercial Center Underwriting Manager preferred. Special Skill Requirement · Knowledge of Microsoft PowerBI, PowerApps, and PowerAutomate, and familiarity with GenAI usage preferred. · Technical expertise in commercial risk selection and pricing. · Analytical thinking skills to make timely, appropriate decisions and recommendations after reviewing all relevant information. · Ability to read and interpret policy contract language. · Broad-based working knowledge of relevant insurance laws and statutes; the contract issue process, computer systems, competitor’s products and marketing practices. · Knowledge of management information and business systems (Word, Excel, PowerPoint, Access). · Excellent verbal, written and interpersonal skills, with demonstrated presentation skills. Physical Actions Required job duties are essentially sedentary work consisting of occasional walking, standing and lifting and/or carrying 10 lbs. maximum, and seeing. Physical Environment Required job duties are normally performed in a climate controlled office environment. Benefits - Farmers offers a competitive salary commensurate with experience, qualifications and location. o CA Only: $102,450 - $174,240 o CO Only: $96,075 - $150,260 o HI/IL/MN/VT Only: $96,075 - $160,710 o MA Only: $96,075 - $160,710 - o MD Only: $96,075 - $160,710 o DC/NJ/NY/OH Only: $96,075 - $174,240 o Albany County, NY/Cleveland, OH: $102,450 - $150,260 o WA Only: $96,075 - $182,625 - Bonus Opportunity (based on Company and Individual Performance) - 401(k) - Medical - Dental - Vision - Health Savings and Flexible Spending Accounts - Life Insurance - Paid Time Off - Paid Parental Leave - Tuition Assistance Job Location(s): R_US - United States Anticipated application deadline: At Farmers, the recruitment process is designed to ensure that we find the best talent to join our team. As part of this process, we typically close open positions within 8 to 21 days after posting. If you are interested in any of our open positions, we encourage you to submit your application promptly. Farmers will consider for employment all qualified applicants, including those with criminal histories, in accordance with the Los Angeles Fair Chance Initiative for Hiring Ordinance or other applicable law. Pursuant to 18 U.S.C. Section 1033, Farmers is prohibited from employing any individual who has been convicted of any criminal felony involving dishonesty or a breach of trust without prior written consent from the state Department of Insurance. It is unlawful in Massachusetts to require or administer a lie detector test as a condition of employment or continued employment. An employer who violates this law shall be subject to criminal penalties and civil liability. Farmers is an Equal Opportunity Employer and does not discriminate in any employer/employee relations based on race, color, religion, gender, sexual orientation, gender expression, genetic information, national origin, age, disability, marital status, military and veteran's status, or any other basis protected by applicable discrimination laws.



