I would like to introduce you to Risto Rossar.

Risto is an insurance innovator and investor, he has been in the insurance business for over two decades. He started with working in an insurance company and went on to build 5 insurtech startups from there. Among them IIZI, the biggest and most innovative insurance broker in Baltic Countries. Cloud-based software platform for insurance agents, brokers and insurers called Insly. And the most recent one – a true innovation, world first insurance marketplace on blockchain Black Insurance.

Risto is a true veteran in the insurance industry, but this is not what I want to focus on today. Risto has built many successful teams and there is something that shines through in every company that he has been running – the atmosphere is genuinely great.

We go into a bit more depth about Risto’s story building these companies and how on earth people love working there so much that they stay. For decades. In the end it will all make sense.


Tell me your story – how did you get into insurance and how did you manage to build not one but many successful companies in the industry?


I started in insurance somewhere back in 2000, when I opened an internet sales platform in Estonia where consumers had the option of comparing insurance prices and also buying policies. We were one of the first to offer online sales in Estonia for insurance products. The company was then called e-kindlustus, which has now become quite a famous brand in Estonia, called IIZI. 

Within a few years I managed to create the biggest insurance broker in the Baltic States. We invested heavily into technology and digitalised all insurance sales and administration processes. At one point I understood that it is rather difficult to scale an insurance business globally. I had a profitable company that had become a dominant player in the Baltic states, but growing out of that geographical area was almost like Mission Impossible for me, because as we all know, insurance is still quite a local business.

I came to the obvious conclusion, that the general level and usage of technology in the insurance industry was very weak, especially on a global scale, compared to what we have achieved here in the Baltic states. So an idea was born. We need to pivot using our experiences through the IIZI platform, to create a solution that would solve the same issues for broker companies in other regions. That is how Insly was born, from a clear need to deliver global insuretech solutions to a vastly under-developed segment. 

Since 2014, our customer base has steadily increased and we are now serving over 700 customers globally through our SaaS technology, to enable businesses of all sizes to sell and administer insurance policies. Insly serves not only insurance brokers but also MGA’s and insurance companies, meaning that our goal is to deliver a product that in universal, both in needed features and functionality.

So that’s what currently takes up the bulk of my time, working closely with the management team and Board to solve this universal need. In addition to Insly, I have also made some investments and I am continuously advising on several other insurtech projects. 


Tell me more about how you’ve built great teams. Nowadays the average time people spend in one company is 2 years. You have team members that are in Insly that started working with you already in IIZI. What makes people stay and want to give their all?


I think it’s a combination of several things. One important part of course is becoming an expert in a certain vertical and in order for us to keep our best people you don’t necessarily need to be the best in the world but you need to be the best in that vertical.

So if you have a developer or manager that has spent the last 7 years building insurance technology then his comparative strength in that field is much stronger than if he’d go to let’s say Pipedrive or Transferwise or Bolt. And that person would feel so much stronger doing something in that specific field because that’s where his competence is. That is probably one element to explain why people might choose to remain in a specific segment. In the IT start-up world, it’s becoming more and more important for technical personnel to have some inherent business know-how of the segment they work in, which adds significant value to any project. This is why we provide regular training sessions about the insurance industry to our staff, so that the technical side of our team can relate to the business value we are actually creating for our customers. 

The other element of course is – I try to really keep an open management style. Everyone is quite free to do whatever they want in our organisation, at least in that the key people who contribute to the success of the company have clearly enough flexibility in deciding what they do and how they do it. That is a very important part of making people happy nowadays. If people feel happy with their work and happy with their colleagues, that’s probably everything you need to keep people motivated. 

insly team

One thing I sometimes struggle with is that I have some people on my teams, whose first job anywhere was at IIZI or Insly. They can sometimes have the feeling – “I am really happy here, it’s really cool but I’ve never worked anywhere else before, so maybe I need to try out something else as well. Do I really want to work all my life in one organisation?” And these conversations are difficult to have because it is a logical feeling. Luckily we haven’t yet lost any of these people, But I feel that I am running out of arguments in these kinds of discussions.

Of course there are some frustrations as well; it’s not like Insly is the place of ultimate happiness without any problems. We face the same challenges as any other organisation that wants to make a significant impact. When team motivation is maybe 6 out of 7 instead of a perfect 10, then this type of issue tends to resurface.  

When motivation is high, then we usually don’t have these kinds of discussions. Usually people need to feel they are developing themselves, and have respect in the workplace. If you manage those two things, then even in the ever-changing landscape of IT, I find that it’s possible to keep staff highly motivated, who have worked for 10-years in the same company.  


It is quite the result when 6 or 7 out of 10 is the motivation level in the unhappy times.


It could be that these numbers are high, but I believe that with the team members who have been working here for a very long time, it’s logical that the general happiness and job satisfaction is very high because otherwise, with current employment market conditions, they would’ve already left a long time ago. I believe that  our top people are really happy with where they are right now, but of course my view is a bit limited.  


Insly has been voted the best workplace in Estonia 2x already. What makes the work atmosphere so great at Insly. You mentioned freedom before but what else that comes to mind? 


I think the most important thing is that the environment needs to be good. When you come to work you need to feel that you are welcome here, everyone is friendly with you, including the management. You know what the company is doing – you have clear information about the company’s results, and why we are doing the things that we are doing is shared with every employee. 

The basic question of “Why?” needs to be addressed very seriously. On a company level and on the individual level. And if for some reason the “Why?” becomes unclear then you very quickly see that motivation in key personnel goes down because they don’t understand anymore what the heck we are doing here: Why we are focusing on this product and why that specific customer and so on and so forth.  

If you solve the why, then I’d say 80% is done. Why + reasonable and common sense management. These are the two very important pillars for employee happiness.

Insly team

Then you have some auxiliary things that may not seem so important individually, but they also help to ensure a positive working environment. Having some fresh fruit in the office, or subsidising health activities like gym memberships, general dental care, or even having a dedicated place for relaxation like we have a massage chair in the playroom. These things tend to add-up and contribute to creating an overall positive and productive environment. 

These types of benefits have become standard practice and a lot of IT companies have these perks, but at the end of the day I believe they contribute to 20% of the overall happiness within the team. For Insly, it is a challenge to compete in terms of benefits, with companies that are swimming in money, but we try to keep it to a reasonable level, and focus 80% on common sense communication from the management about why we are doing things.


What have been your biggest challenges in building companies and teams?


Probably the most difficult time for me has been when the company has plateaued. It is not really going down and it’s not really growing fast enough as well. I have had these moments in almost all the companies that I’ve been running.

You might spend a year or one and a half years when you feel like you’re a little bit stuck. In the startup level you grow maybe only 20-30% per year. Your product is a little bit outdated – the tech is no longer state of the art, things are breaking down. Everyone is looking at the numbers – it’s not a rocket ship anymore, product is full of bugs and it’s kind of crap.

The trick is how to find motivation out of this kind of situation? People want to work at a successful company with the best technologies, and when you lose all these things it becomes very difficult to keep the team motivated. You can throw money at it, you can do backflips or whatever, but it doesn’t really help.

For example during the previous economic crash of 2008, we needed to cut salaries 30% and that was an easier process for me. You know that there is a crisis, you need to act and you can make some direct decisions. But when you are on a plateau and not going in either direction, it’s not so bad that you’ve got to jump in and pivot or create some sort of a revolution, but finding the direction is the biggest challenge. In cases where you can identify the bottleneck, then it’s a natural process which usually leads to growth. The worst case is when things are not very good and not very bad, so you’re not sure in which direction to turn, which is the most difficult period for me.  

You need to push yourself to make some decisions to come out of it, because the pain is not otherwise strong enough to force action.


What’s the most interesting thing you’ve learnt from your team? How do you solve challenges in Insly?


Hmm, I don’t know. I learn something every day. I think probably most of the solutions are probably coming out of the team. It’s not like I am the one who has all the smart ideas. You have challenges in the company. Sometimes they come from me and sometimes from the team. I don’t even know what the ratio is, but I would say probably 80-20. So 80% of challenges that we need to do are coming from the team and they are also responsible for finding the solutions. So then I have the luxury of only being the facilitator. 

In some cases of course the challenge can come from me and the solution from the team or the solution can also come from me. But of course it is always better when the solution comes from the team, because if it comes from me it is much harder to get the team behind it. I suppose that is also in-line with our general management style of facilitating personal and team ownership of delivering results. 

I think the best way how to implement ideas is if the solution comes from the team and the management comes behind it as a supportive element. Then you have the best solution and things can really move fast. As simple as that.

At the end of the day these are all really basic and simple things but the trick is how to implement it. How to make sure that these simple and very intuitive things are actually happening in the organisation. That is where things can actually get stuck, but fortunately we have been lucky.

When a company grows bigger than 5 people it becomes really hard to maintain a shared understanding of common sense and productivity starts lacking. My biggest frustration is actually how slowly things are moving sometimes. You need to be extremely patient, but on the other hand you want to move fast.

This is something that we are dealing with on a constant basis, is how to move fast in an organisation with over 70 people in several countries, so there are plenty of challenges still left to overcome. 


What is your future vision with Insly?


First of all, it all started with software. We are offering software to insurance market players. But our vision is to become the hub or marketplace that connects all insurance market participants. 

On one side there are insurance companies and on the other side there are brokers. If all of these players are using Insly software to manage their business, then we can also connect them and create a marketplace that enables the transactions between our customers. Then we become a much more important player and we can help our customers much more than just solving their efficiency pains. 

We can also solve a critical business line by  providing insurance companies access to a vast distribution network for their products, and giving brokers access to needed insurance products. 

Building the Insly marketplace on top of our software is the bigger vision and we are making small steps towards that already.

risto rossar family


Risto’s management skills are something we can all learn from. Quite often great business ideas get stuck because people cannot find ways how to work together efficiently. Insly and IIZI are true examples of a workplace where people feel happy entering and we should thrive to promote this culture.

P.S. Insly is hiring! Check if you’re a match on MeetFrank.