Director, Digital Insurance Platform (GTM & Product Engineering)

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

QUALIFICATIONS 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 Salaries
• Commitment to your Training & Development
• Medical and Dental
• Telemedicine Benefit
• 401k with a generous company match
• Paid Time Off and Paid Holidays
• Tuition Reimbursement Training Programs
• Wellness Program
• Fun company sponsored events
• And so much more!