Dennis X. Li, FSA

Sharpshooter
DISC Type : CD

VP of Initiatives & Special Ops at Healthcare.com

West Hartford, Connecticut, United States

Overview

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.

Personality Overview

ROI Driven

Precise But Practical

Rigorous & Demanding

They take a lot of pride in personal achievements.  They respond better to strong and respectful interactions. They are not always relationship oriented.

Topics They Care 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.
Embedded Insurance
He has published content specifically analyzing the unique challenges and opportunities for embedded solutions within the life and health insurance markets.

Media Appearances

Dennis has no verified media appearances

Work History

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

Education

Bachelor's Degree from University of Michigan
Master's Degree from University of Michigan

More Information

Social Presence :

Prographics :

Exp : 14 Location : West Hartford, Connecticut, United States Job Level : Senior Designation : VP of Initiatives & Special Ops at Healthcare.com
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Insights For Selling To Dennis

During A Call Or A Meeting

DO's

  • Make sure that you circle back fast on any action items, it wins their trust
  • Hold your ground without indulging in one-upmanship
  • Refer to testimonials from well-known industry leaders

DONT's

  • Do not hesitate from asking counter questions, just avoid challenging their authority
  • Do not back off when challenged, respond with a confident, objective answer instead
  • Avoid being a storyteller and don’t try to oversell

When Cold Calling

When Writing An Email

While Negotiating & Closing

    The secret to closing fast with Dennis is

  • Conviction around the impact matters the most to them, followed by a sense of achievement and ROI.
  • Will you ever get a clear answer from Dennis

  • If they are not convinced, they will say no without any hesitation.

Insights For Deal Planning

    How fast (or slow) will Dennis move?

  • They can reach decisions fairly quickly if they are convinced.
  • Can Dennis take some risk or not?

  • They don’t mind risks but can be quite binary about them.

You And Dennis

Personality Compatibility


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