The Strategist
Jessie Lee
Product & Strategy Lead
Sees the full board — connects product, distribution, and data into a single growth thesis that actually ships.
Jessie Lee is a strategic thinker and product management leader with deep experience scaling hypergrowth Healthcare and InsureTech companies. As VP of Product at HealthCare.com, he was the first product hire and helped transform the company from a traditional lead marketplace into a $1.3 billion InsureTech unicorn — growing sales from $5 million to $40 million in three years while building and leading a team of 10 product managers.
With strong industry knowledge across direct-to-consumer and broker-led distribution in the U65 and Medicare segments, Jessie has a proven track record of building omni-channel distribution in highly regulated industries. His career spans product leadership at Ethos, CoverWallet (acquired by Aon), investment banking at UBS, and eight years at Citi across the Asia Pacific region — giving him a rare combination of product instinct and financial rigor.
Today, Jessie operates as a fractional COO advising companies on GTM strategy, transformation, and hypergrowth — with clients including Forbes Advisor and SmarterTravel. He is also a judge for the Penn Wharton Venture Lab Startup Challenge and has taught Innovation and Entrepreneurship at Stevens Institute of Technology. He is known for picking up diverse industries quickly, asking the right questions to form customer empathy, and turning data analysis into actionable strategy.
Career Timeline
Jun 2022 – Present
Fractional COO
Demarest Ave Partners
Fractional COO providing general management, GTM strategy, transformation, and hypergrowth advisory. Key clients include Forbes Advisor, SmarterTravel, Tangelo, and Financial Wellness Labs. Part of a crisis management team that helped rebuild a major mental health company following a CEO indictment, working closely with government, compliance, clinical, and financial stakeholders.
Jan 2026 – Present
Judge, Penn Wharton Venture Lab Startup Challenge
Venture Lab
Expert alumni judge for Penn's largest pitch competition, coaching student entrepreneurs and providing feedback to drive impactful ventures.
Oct 2022 – May 2024
Adjunct Professor
Stevens Institute of Technology
Taught Innovation and Entrepreneurship to final-year engineering students.
Dec 2021 – Apr 2022
Director of Product Management
Ethos
Led product on life underwriting engines at a company that pioneered instant life insurance approvals through proprietary underwriting technology processing millions of data points. Developed the quarterly roadmap for non-traditional data sources to improve coverage for millions of consumers.
Jan 2019 – Dec 2021
Vice President of Product Management
HealthCare.com
First product hire at a Series C company. Led the growth of omni-channel distribution for U65 and Medicare segments, helping transform the company from a traditional lead marketplace to a $1.3bn InsureTech unicorn backed by Oaktree, Link Ventures, and Axis Capital. Drove 3x conversion improvement and grew sales from $5M to $40M in 3 years. Scaled the product team to 10 members.
May 2017 – Jun 2018
Product Manager, Customer Facing Team
CoverWallet (acquired by Aon)
4th product hire. Led foundational product launches including General Liability, Workers Compensation, and Commercial Auto Insurance, focusing on the checkout platform and carrier integrations.
Aug 2014 – May 2016
Associate Director, Investment Banking
UBS
Real Estate, Lodging and Leisure group. Built financial models for M&A transactions and capital offerings. Lead associate for a $1B credit facility for a major Vegas gaming operator.
Jun 2004 – Jul 2012
Credit Analyst → Assistant Vice President
Citi
Eight years spanning credit analysis, B2B account management for Fortune 1000 clients, underwriting, and payments across the Asia Pacific region. Selected for Citi's Asia Pacific High Potential Program (top 5% globally). Led KYC/AML due diligence for the largest IPO in Singapore (Global Logistics Properties).
Sep 2003 – Jun 2004
Change Management Consultant
Accenture
Led customer journey mapping and process harmonization across 9 institutions. Selected within the analyst class to attend Core Analyst School in Chicago.