Leadership
Proven ability to unlock value across product, strategy, and financial management.
Meet the operator
Jessie Lee
A serious car accident — three days in the ER after being hit while walking her young son home from a playdate — sharpened Jessie's sense of what she wanted the next chapter of her life to look like. Finding the signal in the noise
Jessie spent the most recent years in VC-backed insurtech. She also earned her own health and life insurance licenses — now active in 42 states (NPN 19069726) — to build credibility with carrier and agency partners. Today she advises insurtech founders and growth-stage distribution platforms on GTM, Product, Strategy and Value Creation.
Life & health industry expertise
Carrier relationships, product-market fit & regulatory fluency
15+ years building and scaling life and health insurance platforms. Deep carrier relationships, regulatory fluency, and product-market fit expertise across ACA marketplace, Medicare Supplement, term life, and supplemental insurance.
- Scaled Pivot Health from $5M to $40M ARR
- 5x conversion lift through customer journey optimization
- Carrier integration and quote-to-bind workflows
Legal, strategy & GTM
Governance, organizational design & market launch
Built high-performing teams and organizational structures. Designed and executed GTM strategies for new verticals. Regulatory compliance for new vertical launches
- Go-to-Market and new vertical launch
- Team building and organizational design
- Regulatory and Compliance
Finance & FP&A
Financial modeling & capital strategy
Portfolio analysis, unit economics, and financial modeling in regulated industries. Designed capital-readiness initiatives improving cash conversion 3x. Built financial models for strategic planning and M&A.
- Capital-readiness & revenue cycle management
- Unit economics & portfolio analysis
- M&A and strategic planning models
Let's talk
Building in insurance, distribution, or AI? Let's compare notes.
Thirty minutes, no deck. We'll figure out quickly whether there's signal between us.