Director, Digital Insurance Platform (GTM & Product Engineering)
Cook County, IL - USA
Job Summary
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
- 815 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.
Required Experience:
Director
About Company
WIN's marketing expertise coordinates its members companies' marketing and branding, creating awareness and opportunities for agents and their customers