Dennis X. Li, FSA in

Dennis X. Li, FSA

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VP of Initiatives & Special Ops at Healthcare.com
📍 West Hartford, Connecticut, United States

Dennis is an insurance strategist and speaker focused on driving growth through strategic partnerships. An actuary-turned-entrepreneur, he leverages data analytics to bridge gaps across the insurance value chain. Colleagues describe him as driven, curious, and a strategic thinker with degrees from the University of Michigan.

Outside of his direct roles, Dennis is a member of Pavilion, an exclusive, invitation-only community for top global executives. This indicates a strong commitment to continuous professional development and networking with other leaders in the growth, sales, and operations space.

He has authored articles on the specific challenges and opportunities within embedded insurance and B2B2C go-to-market strategies.

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Experience
14 Years
Current Role
VP of Initiatives & Special Ops
Job Level
Senior
Location
West Hartford, Connecticut, United States
Personality Overview

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Communication Style
Decision Approach
Work Preference

Behavioral traits and communication patterns that shape how this person evaluates opportunities, builds trust, and makes decisions in professional settings.

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Priorities

Topics Dennis cares about

Insurance Distribution
He frequently speaks and writes about the future of insurance distribution, focusing on how to achieve scalable and cost-efficient growth through new channels.
Strategic Partnerships
His career centers on building and scaling partnerships across the value chain with affiliates, carriers, and marketing alliances to strengthen market position.
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Career

Work history

1-2026
VP of Initiatives & Special Ops
Healthcare.com
8-2025 - 1-2026
VP of Strategic Partnerships
Healthcare.com
1-2023 - 8-2025
Director of Business Development and Partnerships
Amplify Life Insurance
2-2021 - 6-2021
Portfolio company (2021 Cohort)
Global Insurance Accelerator
1-2021 - 1-2023
Head of Strategy, Growth and Partnerships
Reeske
In the press

Media appearances

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Education
Bachelor's Degree
University of Michigan
Master's Degree
University of Michigan
Social presence
in
Behavioral profile

DISC profile (public)

DISC behavioral profile

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