Sam Rea in

Sam Rea

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CTO at Aspire General Insurance
📍 Wheaton, Illinois, United States

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.

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Experience
25 Years
Current Role
CTO
Job Level
Leadership
Location
Wheaton, Illinois, United States
Personality Overview

How Sam shows up

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 Sam cares 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.
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Career

Work history

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

Media appearances

No media yetWe could not find public media appearances for this person.
Education
11-2023 - 2-2024
Artificial Intelligence
University of Chicago
1992 - 1993
MS
Stanford University
Social presence
in
Behavioral profile

DISC profile (public)

DISC behavioral profile

Dominance, influence, steadiness, and calculativeness scores with guidance on how this person prefers to communicate and decide.

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Family & Co
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