At CEO (Boardroom Media) we track over 1,000,000 startups and over 5,000,000 people who hold key positions in these companies. We use this directory of startups to highlight top employees, founders and board members we think deserve more appreciation than they are currently getting.
This list showcases the top Chicago based CEO’ operating in the InsurTech space. If you think a CEO’ is missing from this list, feel free to contact our editor on [email protected].
The individuals on this list have been included because of exceptional performance in one of the following categories:
- Innovation – Operating as a key part in an extremely innovative business or startup.
- Growth – Operating as a key figure in the growth and upscale of a market leading business or startup.
- Management – Showing exceptional management skills.
- Societal impact – Putting their business on the map for their positive societal or environmental impact.
Our Data – We source our data from OSINT (open source intelligence) and public directories such as Crunchbase, SemRush and many more. The data from these sources should be treated with a degree of caution and verified yourself.
Kyle Nakatsuji
Co-Founder & CEO of Clearcover
Kyle Nakatsuji is the CEO and Co-founder of Clearcover.
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About Clearcover, Creative Destruction Lab (CDL): Affordable car insurance that’s smarter, faster & puts your needs above all else, helping you make informed decisions every step of the way.
Brad Weisberg
Founder & CEO of Snapsheet
Brad founded Snapsheet in 2011 and has led the company through multiple hyper growth stages. He is passionate about developing creative solutions for today’s complex problems, using powerful technical platforms to deliver great user experiences. He is a champion for the Chicago tech community and regularly mentors leaders at emerging tech companies. His work with Snapsheet has been featured in Forbes, The Wall Street Journal and Fast Company. Brad has a bachelor’s degree in marketing and advertising from Indiana University Bloomington. He is a guest lecturer at Northwestern University.
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About Snapsheet: Snapsheet delivers claims experiences through its cloud-native claims management software and tech-enabled appraisal services.

Ryan Letzeiser
CEO and Co-Founder of Obie
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About Mac Properties, Obie: Obie is an insurtech startup that offers insurance and risk management for real estate investors.
John-Isaac Clark
President & CEO of Arturo
Presently, I serve as CEO for Arturo, a deep learning spin-out from a Fortune 500 company focused on delivering insights to the residential and commercial property insurance and commercial real estate sectors. I’ve been a founder, high-tech executive, and technology strategist with a deep start-up background in Geospatial/Location based services, applied machine learning, big data analytics, cloud computing, and highly distributed systems for the last decade of my career. I thrive and excel at taking technology innovations from concept to product to market and successfully managing and exciting teams both small and large to achieve this quickly.
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About Arturo: Arturo is a deep learning spin-out from a Fortune 500 company focused on delivering highly accurate measurement and predictive data.

Tyrre Burks
Founder and CEO of Player’s Health
He is the Founder/President TeamInterval. His passion is to see how many ways he can disrupt the Sports industry with technology. Tech-driven athlete before Team Interval, He was a professional football player for the NFL, European, and Canadian football leagues. He have identified a true need in the marketplace, that has received the attention from collegiate and professional sports organizations all over the world.
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About Player’s Health, Sports Defense: Player’s Health is an insurance agency that protects athletes and sports organizations with a unique risk management platform.
Dan Kazan
CEO and Board Member of Insureon
Dan Kazan is the CEO at Insureon.
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About Insureon: Insureon is the number one independent marketplace for online delivery of small business
Ilya Preston
Co-Founder & CEO of PAXAFE
Ilya Preston is the CEO and Co-Founder of PAXAFE,
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About PAXAFE: PAXAFE builds smart packaging IoT that aggregates critical supply chain data and enables intelligent shipping insurance.
Brian Hoffman
Founder & CEO of Nomad Credit
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About Nomad Credit: Nomad Credit is a financial marketplace for those under-served by other marketplaces.

Heather Holmes
Founder & CEO of Genivity
When a close relative was hospitalized in 2010 and nearly died, Heather realized if her family had known about the specific health threats he was vulnerable to, they might’ve been able to prevent his health crisis. Heather also realized we need sound, unbiased, and up-to-date information about treatment options. What’s more, every family needs that. Heather founded TapGenes to help families understand the unique and personal connection between a family’s health, lifestyle, and surrounding environment. Helping families connect the dots between their known risks and helping them discover where they can impact and influence better health. Prior to founding TapGenes, Heather led global market development strategy for a multi-national medical device company. Working in India and China inspired her to explore ways to provide simple yet reliable health information and solutions that could be managed within the family. After completing an expat assignment in Singapore, Heather was determined to create a solution to help families care for each other that is simple to use, clinically relevant, and visually focused to transcend language barriers. She graduated from the Founder Institute in Singapore in 2013. Heather has 10 years of experience in sales, marketing, and market development within the medical device space. Prior to that, Heather was a TV news reporter for a CBS affiliate in Michigan.
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About Genivity, TapGenes: Genivity is a platform that tracks and predicts family health risks to help financial advisors better serve their clients.