Sam Rea

Commander
DISC Type : D

CTO at Aspire General Insurance

Wheaton, Illinois, United States

Overview

Sam Rea is a technology leader with 25 years of experience in the insurance industry, currently serving as CTO at Aspire General Insurance. He specializes in digital transformation, M&A, and scaling technology organizations, with an MS from Stanford University.

He has a proven track record of leading large-scale growth, notably transforming National General from a $1B to a $5B company and facilitating its sale to Allstate.

Personality Overview

Decisive

Very Quick

Strong-Willed

They prefer to move quickly, and expect the same from others.  They do not care very much about building rapport or relationships. They like to stay in control of the negotiation or defining of the terms.

Topics They Care About

AI in Insurance
He actively discusses how AI is reshaping insurance operations, including areas like fraud detection, claims triage, workflow automation, and virtual assistants.
Digital Transformation
Focuses on replacing legacy platforms with modern, cloud-native solutions to improve efficiency and drive revenue, as demonstrated in his previous roles.
InsurTech Innovation
A frequent speaker at major industry events like InsurTech NY, sharing ideas with top professionals on insurance innovation and technology strategy.

Media Appearances

Sam has no verified media appearances

Work History

9-2024
CTO at Aspire General Insurance
1-2022 - 9-2024
Chief Technology Officer at PEAK6 InsurTech
1-2021 - 7-2022
Chief Technology Officer - National Flood Services at PEAK6 InsurTech
11-2017 - 1-2021
EVP, Chief Information Officer at National General Insurance
10-2016 - 11-2017
Senior Vice President - Application Development at National General Insurance

Education

11-2023 - 2-2024
Artificial Intelligence from University of Chicago
1992 - 1993
MS from Stanford University

More Information

Social Presence :

Prographics :

Exp : 25 Location : Wheaton, Illinois, United States Job Level : Leadership Designation : CTO at Aspire General Insurance
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Insights For Selling To Sam

During A Call Or A Meeting

DO's

  • Objectively showcase the impact that your product creates
  • Be respectful but crisp
  • Refer to testimonials from well-known industry leaders

DONT's

  • Do not hesitate from asking counter questions, just avoid challenging their authority
  • Avoid being too verbose
  • 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 Sam is

  • Confidence in impact is paramount to them, followed by a sense of achievement and ROI.
  • Will you ever get a clear answer from Sam

  • If they decide not to go ahead, they will say no without hesitation.

Insights For Deal Planning

    How fast (or slow) will Sam move?

  • If convinced, they can reach decisions quite fast.
  • Can Sam take some risk or not?

  • They do not shy away from taking risks, but can be quite binary about them.

You And Sam

Personality Compatibility


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