We are seeking a strategic, hands-on leader to build and scale a best-in-class, consumer-facing digital insurance sales platform. This role owns the end-to-end digital business-from customer acquisition through quote, bind, and payment-while ensuring a seamless, compliant, and high-converting user experience.Sitting at the intersection of product, engineering, marketing, and insurance operations, this leader will define and execute the go-to-market (GTM) strategy while simultaneously driving platform innovation and performance. The role carries full accountability for digital revenue growth, customer experience, and unit economics across all markets.DUTIES & RESPONSIBILITIES:Platform & Product OwnershipOwn the end-to-end digital insurance platform including quoting, binding, payment, and customer experience Lead platform architecture, system integrations, workflows, and data strategy Drive UX/UI design and continuous optimization to improve conversion and reduce friction Oversee development teams and vendors to deliver scalable, high-performing solutions Go-to-Market Strategy & ExecutionDevelop and execute comprehensive GTM strategies aligned to growth and revenue goals Define target segments, positioning, pricing strategy, and channel approach Lead cross-channel execution including digital acquisition, partnerships, and distribution Growth & Performance ManagementOwn core performance metrics including conversion rates, CAC, and revenue growth Establish KPI frameworks and dashboards to monitor funnel performance Continuously optimize acquisition, conversion, and retention through data-driven insights Market & Competitive IntelligenceConduct ongoing market research and competitive analysis to inform strategy Identify emerging trends, customer needs, and opportunities for differentiation Cross-Functional LeadershipAlign engineering, product, marketing, underwriting, and operations around a unified strategy Drive execution across teams with clear prioritization, timelines, and accountabilityAct as the central decision-maker balancing growth, compliance, and technical constraintsQUALIFICATIONS REQUIRED:8-15+ years of experience in P&C personal lines insurance products with focus on digital products, Insurtech, e-commerce, or related fields. Proven track record of owning and scaling a revenue-generating digital platform or funnel from product management, customer journey design, sales & marketing and conversion optimization Demonstrated success in developing and executing GTM strategies in a digital environment Experience working with engineering teams on platform architecture, APIs, and integrations Strong analytical mindset with experience using data to drive decisions and performance improvements Ability to lead cross-functional teams and operate effectively in a fast-paced, high-growth environment Success in this role requires a hybrid leader who can seamlessly integrate product, technology, and growth strategy-owning outcomes from platform design through revenue generation.Warrior Insurance Network (WIN) provides a competitive benefits package to all full-time employees. Following are some of the perks First Chicago employees receive:Competitive SalariesCommitment to your Training & DevelopmentMedical and DentalTelemedicine Benefit401k with a generous company matchPaid Time Off and Paid HolidaysTuition Reimbursement Training ProgramsWellness ProgramFun company sponsored eventsAnd so much more!Estimated Compensation Range: $125,000/year-$180,000/year**Published ranges are estimates. Offered compensation will be based on experience, skills, education, certifications, and geographic location. In addition, starting salary may vary by position depending on whether the position is in-office, hybrid or remote.
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