Director Insurtech Jobs in Illinois (NOW HIRING)

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 Ownership
• Own 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 & Execution
• Develop 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 Management
• Own 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 Intelligence
• Conduct ongoing market research and competitive analysis to inform strategy
• Identify emerging trends, customer needs, and opportunities for differentiation
• Cross-Functional Leadership
• Align engineering, product, marketing, underwriting, and operations around a unified strategy
• Drive execution across teams with clear prioritization, timelines, and accountability
• Act as the central decision-maker balancing growth, compliance, and technical constraints

Background & Experience

• 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.