Michael DeWitt

Judge
DISC Type : Dc

Managing Director, Platform Software Engineering at Inspira Financial

Austin, Texas, United States

Overview

Michael DeWitt is the Managing Director of Platform Software Engineering at Inspira Financial, where he leads the engineering, product, and design teams. His focus is on consumer-directed healthcare benefits platforms. He holds a Masters degree from The University of New Mexico.

Outside of his core role, Michael shows immense pride in his teams accomplishments and maintains a personal connection to his hometown of Chicago. He actively follows developments from his alma maters, Indiana University and The University of New Mexico.

His former company, First Dollar, where he served as CTO, was successfully acquired by Inspira Financial in November 2024.

Personality Overview

Features Driven

Quality Focused

Objective Thinker

They like to be in a position where they can control the conversation and terms.  More than the product, they care about the effectiveness of the product. They are very proud of what they do.

Topics They Care About

AI in Healthcare
He highlighted AI's ability to accelerate product development and act as a knowledge base in the complex healthcare and benefits landscape.
Fintech Innovation
His work involves creating platforms for banks and financial institutions, and he celebrates partnerships and integrations within the fintech ecosystem.
Engineering Leadership
He publicly praises his team members for their contributions, showcasing a leadership style that values and promotes individual achievements.

Media Appearances

Michael has no verified media appearances

Work History

6-2025
Managing Director, Platform Software Engineering at Inspira Financial
11-2024 - 6-2025
Technology Leader at Inspira Financial
1-2023 - 11-2024
CTO at First Dollar
2-2022 - 1-2023
VP of Engineering at First Dollar
7-2020 - 2-2022
Director Of Engineering at First Dollar

Education

2011 - 2013
Master's degree from The University of New Mexico
2007 - 2011
Bachelor's degree from Indiana University Bloomington

More Information

Social Presence :

Prographics :

Exp : 8 Location : Austin, Texas, United States Job Level : Mid-senior Designation : Managing Director, Platform Software Engineering at Inspira Financial
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Insights For Selling To Michael

During A Call Or A Meeting

DO's

  • When negotiating terms, help them build an impression that they are the ones calling the shots
  • Refer to testimonials from well-known industry leaders
  • Make sure that you circle back fast on any action items, it wins their trust

DONT's

  • Don’t take too much time in sending them information if they ask for any
  • Do not back off when challenged, respond with a confident, objective answer instead
  • Don’t be in a rush to invite them for a social meet and greet

When Cold Calling

When Writing An Email

While Negotiating & Closing

    The secret to closing fast with Michael 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 Michael

  • If they decide not to use your product, they will say no clearly.

Insights For Deal Planning

    How fast (or slow) will Michael move?

  • They can take decisions very fast if you manage to convince them.
  • Can Michael take some risk or not?

  • The risks don’t matter much to them.

You And Michael

Personality Compatibility


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