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Meet Risto Rossar, Insly’s CEO

Today’s interview has been worth the wait - we have our CEO Risto Rossar in the hot seat.

Risto says that by founding Insly, his plan was to build a geographically scalable business and help the insurance industry to become more digital. That’s why he dug into the world of IT. As one the most exciting projects, Risto points out the process of building our world-class product and participation in customer calls. That is an invaluable source of information and a good way to get direct feedback to how our products have helped them.

Continue reading to learn more about how Risto describes his journey, including what led to the genesis of Insly.

Please describe the journey of founding Insly. When and why did you come to a realisation to start Insly?

After spending 14 years to build the biggest insurance broker in the Baltics, IIZI, from scratch, I realised two things:

  • the insurance broker business is not geographically scalable;
  • most of insurance businesses are not technologically very advanced.

My plan was to build a geographically scalable business and help the insurance industry to become more digital. That’s why I decided to sell the broker business and dig into the world of IT. I was already in the IT space since IIZI was partially an IT business.

You are the CEO at Insly. As simple as possible: what’s your job like and how does that help customers?

I set the vision for Insly, remove obstacles, and make sure we have enough funds to develop superb insurance software. If I do my job well, then Insly delivers the product that makes our customers happy.

What makes Insly different from other insurtech companies?

This comparison is really hard to make, but let’s give it a shot. What truly differentiates us is that:

  • we are from Estonia, the country with the highest rate of unicorns per capita in Europe;
  • out of all Estonian insurtechs, our office is the closest to the airport.

Yes, these two things make us really stand out from all the other insurtechs in the world.

Describe Insly in three words.

When I think of Insly, these three things come to mind:

  • freedom - Inslians have the flexibility of arranging their work just the way they want;
  • accountability - our people are responsible and trustworthy, because freedom should not come at the expense of commitment and accountability;
  • transparency - we are transparent about everything – numbers, plans, failures, risks, successes, skills, worries, etc. We do not sugarcoat the truth, but you can always trust that it was given for a good reason.

Can you point out some of the most interesting projects you have been involved in?

The most interesting projects to me are linked to two things:

  • building the product. Lately, my direct involvement in that is rather small, but I have really enjoyed the process of how our product teams are building world-class products;
  • participating in customer calls that give direct feedback to how our products have helped them. It can be a sales call or just a conversation with an existing customer. This is an invaluable source of information to us.

How do you spend time off work?

I have four kids, so it is very easy to fill in all my free time. I also like different kinds of surfing, mostly windsurfing. One of my most expensive hobbies is investing in other start-ups. From an intellectual level, I am very interested in macroeconomics (mostly Austrian) and crypto and how this will change the world we live in.


Don’t forget to read previous interviews with Pamela Raestu, Hammad Mirza, Kaspar Ilves, Märtin Kosk, and Ott Kell. Stay tuned for more stories introducing team Insly!