Director of GTM and Product Engineering​/Insurance

A growing insurance organization in the south suburbs of Chicago is hiring a full-time senior digital leader to own and scale a consumer-facing insurance sales platform. This role focuses on modern digital product development, e-commerce‑style funnels, and data‑driven growth within a regulated insurance environment. The platform spans quoting, binding, payment, and customer experience across multiple markets. This will be hybrid, three days in office.

This is a rare opportunity to step into a role with full ownership of a digital P&L. The company is seeking a leader who thrives at the intersection of product, technology, and growth strategy. You’ll have the autonomy to shape the platform roadmap, influence go‑to‑market strategy, and directly impact revenue while working alongside experienced engineering, marketing, and insurance teams. Ideal for someone who wants both strategic influence and hands‑on execution in a high‑growth environment.

• 8+ years of experience in personal lines P&C insurance with a strong digital focus
• Proven ownership of a revenue-generating digital platform or sales funnel
• Experience leading digital product strategy, customer journeys, and conversion optimization
• Strong understanding of quoting, binding, and payment workflows
• Ability to partner closely with engineering and technical teams

• Insurtech or e-commerce background
• Experience owning GTM strategy and digital acquisition channels
• Data-driven mindset with strong KPI and dashboard experience
• History of leading cross‑functional teams

• 40% Digital product and platform ownership
• 30% Growth strategy, GTM, and performance optimization
• 30% Cross‑functional leadership and stakeholder alignment

• 50% Hands‑On strategic execution and decision‑making
• 30% Management and team leadership
• 20% Team collaboration across product, engineering, marketing, and operations

• Bonus eligible

• Medical, Dental, and Vision Insurance
• Vacation Time
• Long‑term incentive or equity participation

Applicants must be currently authorized to work in the US on a full‑time basis now and in the future.