The world of insurance is complex, slow-moving and in much need of digital transformation. Shift Technology’s Jérémy Jawish, Eric Sibony and David Durrleman set out on a mission to transform it, delivering the only AI-native decision automation and optimization solutions built specifically for the industry. Since the company’s founding in 2014, Shift has made a name for itself in the insurance world, announcing its $220 million Series D round and a market valuation of more than $1 billion. The company now serves more than 100 customers in 25 different countries and has analyzed nearly two billion claims.

Getting to this point has taken time, determination and passion from a team of first-time founders who saw an opportunity to fix a broken global industry by taking an international and multi-product approach early on. I sat down with Jérémy to discuss his decision to build a company from scratch, the importance of trust when it comes to co-founders and the board, why passion is so important, his tips on choosing investors and much more.

Let’s start at the beginning - you were an intern at a large insurance company. When did the idea of Shift emerge? 

I first thought about entrepreneurship because I wanted to work with Eric, my co-founder, on something that was ours. During my internship, I realised there was something broken in the industry. The experts were looking at everything manually, even though there was so much we’d studied in mathematics that could be applied. 

So there was definitely an opportunity for a software service. At the same time, I felt that if I could do anything, I’d do it with Eric. He’s one of the smartest people I’ve ever met and passionate about the subject. That’s how it came about. 

When did you know that it would be a company you’d start from scratch?  

It was very natural. Eric, David, and I didn’t ask ourselves a lot of questions. We went for most things on gut feeling. This is how we built the company. We did what we felt was right rather than relying on an Excel spreadsheet. 

The way we looked at it, thought about it, and worked together just came naturally. We started building the company without even realising it. That only happened formally when someone told us we needed to create a legal entity so that we could hire someone. 

Insurance is a tough space, why did you go for that sector?

When I arrived in France, I hadn’t even heard of insurance – we didn’t have any in Lebanon. It’s only when I had to get home insurance that someone explained to me how it worked. I knew I wanted to do that. 

At one point, the insurance sector was too slow. We didn’t know if the company was going to make it. So we tried other sectors, like eCommerce. But we felt our added value was really going to be in insurance – this is where we had to make the decision. We’d done our seed round, and one of our investors felt we needed to shift out of insurance as the sales cycle was too slow – we’d had no customers in the year since investment. But we did have PoCs in three or four eCommerce companies.

This was a point where we really followed our gut feeling. We knew insurance was slow and complicated, but that was a big barrier to entry, and we said as much to our seed investor. This was the toughest early-stage decision we had to make – telling our investor that, even though we were good at eCommerce, we were going to focus on insurance instead. We knew we had to go for it.

Tell us how you managed to navigate this old-world industry, and create the brand, and credibility. What advice would you give to entrepreneurs trying to take on sleepier vertical industries?

It’s all about the people you hire. The founder of Veeva told me that when you go after a traditionally slow and complicated industry, it can become very tiring, very quickly. The most important thing is to hire people that are passionate – and passionate about the sector. Hire people that won’t leave after six months – when a big company pulls out from signing a contract, for example.

You need to hire people who are willing to accept failure after a long period of working hard on something that maybe doesn’t come through. 

How do you make people passionate? Tell us about the vision and the values you’ve had to build to do that.

Vision and culture start with the founders. It’s like with kids - they do exactly what their parents do. You can pretend, and say whatever you want, but you need to walk the talk. Whatever you want to do with your company, you need to start with yourself. 

If you embrace the vision, and believe you’re going to give a big part of your life to achieving it, you should start your company, hire people, and make them passionate. If you’re not ready to accept hard work, failures, and stress in pursuit of that vision, it won’t work. If you’re not passionate about the sector and what you’re doing, you should do something else.

Whatever you do at an early stage, the culture starts with you.

Treat people well, and the culture will be around treating people well. Optimise cash, it’ll be around optimising cash. If what you value is R&D, everybody will focus on that and that will be the culture. I don’t think founders can create a culture in a company that they don’t have in their DNA. The company is going to be who you are. 

I’m really happy that I’m not the only founder at Shift. Having co-founders helps you limit those parts of the culture you don’t want to spread, while taking from them the best culture they have. This is what’s made us what we are today – Shift is the best of me and my co-founders. 

It’s not that common to have the three co-founders still at the company. How did the three of you navigate who should be CEO from the start?

It wasn’t obvious. Eric and I had always been equal in everything we’d done. And David used to be my boss. But we had to decide, so I stepped forward, and said I’d be the CEO and drive things. The first month wasn’t easy or natural. It took us time to adapt. 

Trust is essential. We made the decision that I was CEO – they trusted me, and I trusted them, even if they initially   had doubts. But it’s not obvious – especially when it’s everyone’s first company. 

I want to talk more about trust, not just between your co-founders but with your board. You really use the company’s board and get a lot out of it. Tell us more about governance and your journey here. 

As a founder, it took me time to realise that the board isn’t a court of audit justice. It’s not there to judge the CEO. This is probably my first big mistake – thinking the board was there to tell me whether I was doing a good job or not.

One thing that’s changed is that the board functions independently. When I met Lars [Björk, former CEO of Qlik] we just clicked and I trusted him. He helped me understand two things: that the board wasn’t there to judge me or decide if I was good at my job, it was there to help the company get where it wanted to go. 

I also came to understand that, at the end of the day, investors and board members are real people. When I understood that it was a team, not an organisation, I then realised I should choose people I want to work with, rather than funds. People I wanted to think with and spend time with as human beings. Once I understood this, the dynamic changed completely.

What advice would you give to entrepreneurs about how they should think about their investors, venture capital, and how they should build the board? 

This is one of the most important topics and a lot of rubbish has been written on it, which makes it tough when you’re starting your first company and don’t know any better. We chose our investors because we wanted to work with them – it was never about the valuation. I don’t know how many companies can say their Seed, and Series A, B, C, and D investors have put money in at every round, and I don’t know if there are many founders like David, Eric, and me, who haven’t taken the highest valuation at every round. But I’m glad I took a percentage cut on valuation at some of these stages, because the company wouldn’t be where it is today.

Choosing investors is one of the most important decisions for a company – especially when you’re in it for the long term. You need to be very careful who you choose. When you look at your board’s and your VC’s function, you want someone who truly believes in your vision. 

But before making any decision, every entrepreneur should spend a month or two with potential investors before raising money. This will help ensure you pick the right one to join your journey for the next six or seven years. And remember that everyone’s a human being. You’re not just choosing a VC, you’re choosing a person with their own aspirations, lives, families and problems, and you should choose someone that shares your values. 

You’re very focused on the individual - especially when hiring your team. What have you learned about your judgement of people’s characters and the importance of EQ? 

As an entrepreneur, you’re going to spend most of your life with your colleagues – more than with your partner and your family in those critical years. The first question I ask myself when I hire someone, as when choosing investors, is: “Am I going to be excited about working with this person every day? I want to think about what I can learn from this person. We’re still learning, we learn everyday and I’m not a serial entrepreneur that’s done a lot of other things so I want to learn from others.

As a CEO, certainly at the start, it’s not easy hiring someone more senior – someone who’ll carry a lot of weight, who’ll have stock options, and be seen as a big deal in the company. Once you get over this, you’ll start enabling the huge potential within your company. Once again, it comes back to trust. 

If you find someone you’re excited to work with, that you can learn from, and that you can trust, it’s a no-brainer. These three things are more important than any salary increase or valuation, because they’re for the long term. And if one of these things breaks, it doesn’t mean you won’t stay friends. You’ll probably suffer, but you need to find a way to fix it. 

You’ve built a global company, and had to do it early on.  How easy or difficult was it to do that, given the more complex sales cycle? 

We had a big ambition – we wanted to go after the world of insurance. But it’s definitely one of the most difficult things I’ve done. We’d hired an international team from day one – we have 40 nationalities – so culturally, it was relatively easy. It was physically tough, though, because of the need to meet customers wherever they are - Singapore, Mexico, Hong Kong and so on. This is an area where the board helped a lot, by not judging me. 

You need to fly all over if you want a global footprint. But as a founder, you need to stop doing it yourself. It’s great to go to Singapore, say, but at some point you need to refocus and hire the right people in each geography who you can trust to do it for you. This is where investors can help, finding talent. 

You also built a multi-product company at a very early stage. What are your learnings from this?

We didn’t become multi-product because we thought we needed to be a multi-product company. It was because of our ambition and passion to change the insurance world. When I landed in France and discovered you can pay someone say $20 a month and they’ll cover things for you, I thought this [insurance] was amazing and wanted to make it the coolest industry in the world.

We wanted to fix everything that was broken, not just a few things. We had the relationships, we had the customers, and they trusted us, so it came easily. But we needed someone to say, “we want to do this”.

This is advice every founder should have. Don’t try to do something or think about doing it – just do it. It’ll be tough - in vertical software you can spend so much time just cracking the first product. If you’re not passionate, you won’t want to go through all that again. But we had that passion. We did it. So we did it again. 

After a few years, you’ve decided to move your family to the US. Talk about this, how important the US is, and how you manage to keep the centre of gravity. 

I was spending my time between here and the US, where I had an apartment. I did this because I’d seen a lot of companies die because their culture was disrupted. They’d had a big footprint in a particular country and then suddenly left – whatever team and foundation they had in place collapsed. I needed to be able to transition our culture to the US without changing that culture to become American. 

I decided to relocate because I understood that, to really penetrate a market, you need to live its culture. And I realised that the moment was now, because I need to better understand that culture. It’s the right test for entrepreneurs – do they want to walk the talk or just say they’re going to move someday?

For me, it was a family decision. We see the move as an opportunity not only to have a multicultural company, but to have a multicultural family too. 

Are there any aspects of being a European entrepreneur and building a global business that aren’t discussed enough?

In general, I think European founders are discouraged from going to the US. You can pick some great local investors and build a business in France, for example. But if you want to go after the US, you need to choose an investor that will help you understand how important it is, and that you shouldn’t be afraid of it. Some will tell you it’s a nightmare, that it’s going to be hard, that you’re going to suffer and that so many companies have failed. That’s why a lot of entrepreneurs in Europe see scaling into the US as impossible.

You need investors who can say look how many companies have done it successfully and how we’ve helped them.

You have a family now, with a young baby. Do you have any advice for young founders as they build family life and still have the intensity of growing a business?

I was afraid to have kids. I didn’t know how I’d manage a kid and a company. Now I’m aware I’m much more prepared for the company now that I have a kid. Taking care of my daughter made me realise that, when you want to find time for something, you’ll find it. It also made me realise that, at work as at home, you should make time for things that matter. It’s easy to say, but until you’ve lived it, it’s hard to understand. You have the power to focus on what matters.

Again, it has made me appreciate that I need to walk the talk. When I’m stressed, she’s stressed. When I’m happy, she’s happy. Since she arrived, I’m aware of how much I represent the company internally. It sounds obvious, but when it’s your first job, your first company, and your first baby, you’re very much self-taught.  

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