Let's be honest, nobody gets excited about insurance.Yes, it's necessary but we've all been there on the phone, pulling out our hair! And the problems can be ten-fold with freelance insurance. But what if we told you, everything that drives you crazy about insurance, is changing?

Now that's something we can get behind. Many insurance companies tell us we can trust them, so what makes Sherpa different? This month we spoke to Chris Kaye, CEO and Co-founder of Sherpa, to understand his motivation behind Sherpa and his mission to reinvent insurance as we know it.

Chris, tell us about Sherpa, what inspired you with this venture?

I have worked in insurance for many years, and was getting really frustrated by the inability of insurers to change how they interact with consumers. Locked into an inflexible, product view of the world, I felt like they weren’t moving with the times. So we asked: why can’t we insure you as a whole person across all of your risks, rather than as a collection of individual complex, confusing and disjointed policies for each risk? And why can’t that insurance change with you as your life changes?

This is the fundamental premise behind Sherpa: holistic, bespoke and flexible insurance solutions.

Insurance has traditionally been seen as a ' necessary evil' ! What are you looking to change?

The reputation of insurance gets me really mad! It is such a critical part of our lives - a really important way to help us achieve our dreams, and protect us against our nightmares. And yet everybody, me included sometimes!, hates insurance. This is because people have lost trust in insurance companies to act in their best interest. There are so many instances (the PPI mis-selling scandal, the egregious raising of premiums on renewal, hidden commissions) where the insurance industry has shot itself in the foot, that we felt a completely new insurance model was needed.

So with Sherpa, you get free, regulated advice on what insurance you need; you get a bespoke insurance policy across multiple risks, so there are no gaps or overlaps; this changes as your life changes so it stays up to date; and because we cut out all the middlemen this can be 20-40% cheaper than alternatives.

And, we think best of all, our members pay us a flat subscription fee - totally transparent and up front, and it doesn’t vary based on how much insurance you buy through us, so we are never incentivised to sell you more than you need. This is what we think allows us to create an aligned and trusted relationship with our members, and change the terrible reputation of insurance.

Why have you decided to focus on the self employed and freelancers?

This decision was easy to make. I personally went through the pain and joy of moving from the corporate world into being first a freelancer, and now starting up a small business. Insurance caused me a lot of pain. It took me 20 hours of my time, over two months, to sort out what I needed. And the more I talked to people, the more I saw this was a real problem that needed solving.

We are unloved by traditional financial services companies, who tend to suck in air through their teeth and shake their head when we tick the “self-employed” box on any kind of application form. Sherpa has benefited from many contractors, consultants and freelancers working with us to help achieve our vision - so this is a product built by them, for them.

What has your own research informed you as to what is important to the self-employed/freelancers?

What our research has told us is that freelancers love the freedom and control that comes with a different way of working. But that comes at the cost of security - worrying about where your next month’s income will come from; worrying about what happens if you can’t work for some reason; worrying about making long-term financial commitments when your cash-flow goes up and down unpredictably. It is stressful enough doing the important stuff: winning clients and delivering great work. So we thought it was time that someone put in place a better safety net - like the one an employer provides - so that more people can enjoy the world of freelancing, with much less of the worry.

Having used a number of freelance members of The Work Crowd, can you share how and why as a business you use freelancers?

I think there are three things above all that freelancers have brought to Sherpa, and why they will always be critical to our success. The first is passion, energy. I have found that freelancers bring an extra drive to add value to the business, and the willingness to go above and beyond. The second is that, by nature, they are risk-takers - and we love that quality of edge and willingness to stretch us that this brings. Finally, it is so important to bring new ideas, new ways of thinking, and extra creative juice into the business.

We think that flexible models are the future of work, and we are delighted to be doing our bit to make it easier for people to choose different paths.  

Contact us today!