“We need to tear down information silos” Chris Cheatham, CEO of RiskGenius

Instead of a short bio, let us know what are your top 3 books everyone working on digital transformation needs to read and top 3 tech gadgets one needs to have?

Zero to One. This is the best book on tech and so many entrepreneurs don’t understand the key concept: your tech better be 10X better if you want to win (Available in the USin the UK, in Germanyin Francein Spain).

Moneyball. I love this book because it helped me see how someone can look at a problem totally different. In the case of Moneyball, Billy Beane started looking at baseball stats in a different way (Available in Germanyin the USin the UK, in France and in Spain).

The Dip. This is Seth Godin’s best book and it’s super short. 10X better technology takes time. You will hit a new dip every single day. Pushing through the dip is key; 99% of people don’t get through the dip in some form or fashion. (Available in Germanyin the USin the UK, in France and in Spain).

iPhone. I hate my phone and love my phone all at once. I saw some crazy stat that it’s still a better deal at $1000 then most gadgets based on the number of times you touch it in a day (versus everything else). (Available in Germanyin the USin the UKin France and in Spain). Garmin Fenix 5. I was really disappointed with my Fitbit. So I ponied up for a Fenix 5 watch and I absolutely love it. I love how well it is constructed. (Available in Germanyin the USin the UKin France and in Spain).

Calendly (or equivalent scheduling app). I would go insane without this app. Seriously. 

You are not “only” the CEO of Riskgenius but also a renown influencer in the insurance industry? Firstly tell us more about your company. How far are you with becoming the Goolge of Insurance?

We are getting closer every single day. Users can now use our Google-like search to find and compare policy language instantly. Now we are moving to an analytics based approach — put another way, the computers are going to start showing insurance pros what is and is not important. 

When you start a discussion – for example on Linkedin – a lot of experts from around the globe participate. What role plays Social Media in your work as CEO? What would you recommend c-suits of incumbents who don’t have an interactive presence in the internet?

Social media is our secret sauce. I have over 100,000 followers on Linkedin and most of them are in insurance. That is crazy. I use Linkedin to share wins, struggles, and ideas. Some day I would love to go back and read through all my crazy Linkedin posts. 

Most corporate social media is so, so boring. I love the personal touch. And, I guess you have to be a bit controversial. Although I don’t really think my posts to Linkedin are that controversial. For example, I recently posted “You can’t fix front end until you legacy software at an insurance company.” I don’t see that as controversial; others did. 

Life is too short to be boring. 

Since you are such a renown expert: How do you estimate the state of the industry inside and outside the US?

Honestly, we are in the first inning of a nine inning transformation. There are major insurance corporations that are just now scanning in paper documents. Most insurance professionals can’t really find the digital information they need. We have so far to go. 

What do you think are the biggest chances for incumbents to use the digital transformation as a chance? What are the biggest hurdles in your opinion?

The biggest opportunity and the biggest hurdle is tearing down information silos. I can’t tell you how difficult it is to get our hands on  an insurance carriers forms sometimes. This occurs because (1) the information is not stored in a central location and (2) the information gatekeeper does not want to give up the information to a more efficient system.

Herbert Fromme, maybe Germany’s most famous journalist on Insurance topics, said a few weeks ago, that insures can reduce the majority of the tasks in the future and for the rest they need employees with different skillset. What do you think about this?

Absolutely, and this is no different than most other industries. I used to be a litigation attorney. I attained my billable hours primarily by reviewing large document sets on cases. Two years into my career, I started reading about outsourcing operations that would review litigation documents at a fraction of the cost. Two years after that, I started reading about Technology Assisted Review, which involved machines reviewing litigation documents. 

The same thing is happening in insurance. Insurance companies have just gotten comfortable outsourcing many jobs to other countries where labor is cheap. And now you are starting to see machine learning solutions that can do the outsourcing work (ahem, 

What are your Top 3 Do’s and Dont’s for a c-suite, that understands that he or she needs to act soon?


  1. Spend most of your time on the problem. 
  2. Make sure you have buy in from all employees — not just executives. 
  3. Avoid reading traditional tech press — do your own research. 

What would you advise young people that are thinking to enter the insurrance industry?

Go get a job in insurance and pay attention to all of the crazy, frustrating situations that you see. There will be a lot. It is the nature of the beast. Talk to your peers about the problems you are having. See which problems others focus on. Then figure out how to fix the problem you have selected. 

Thank you for your time


Chris Cheatham is the Chief Executive Officer and Co-Founder of RiskGenius. He has been in this position since January 2012. As CEO, Chris leads a team focused on developing the RiskGenius product. Under his leadership, RiskGenius is empowering its customers to review insurance policies faster with Technology Enabled Policy Review. Powered by machine learning and natural language processing, Technology Enabled Policy Review breaks insurance policies down into categorized clauses. 

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