We’re changing the world. But first, we’re changing the world for

the self-employed




Imagine a world where insurance is


Unbiased guidance so you know what you need.


All your insurance in one place.


Designed specifically for you, by people like you.


No hidden commissions, just a transparent monthly fee.


Insurance that changes as your life changes.

People behind sherpa

Meet our team

We are
passionate people,
Advisory Board Chair
Andrew Bentley

Having had first hand experience of business transformed by technology or that have emerged out of the opportunity created by technology, Sherpa stood out for all of the right reasons: A compelling consumer proposition, scalable market opportunity and a talented leadership team.

Sherpa for me has the real potential to be in industry disruptor on a massive scale

Andrius Ševčenko

At Sherpa, I write the code that helps us make it all happen. From the morning standup to evening, I live the code to produce the best experience and functionality.

I enjoy communicating with people and meeting new interesting minds; I'm always up for an all-night party!

Advisory Board Member
Ben Little

I am the co-Founder of Fearlessly Frank, an innovation agency, and key strategic partner to Sherpa. We joined forces with a not-so-simple ambition—to disrupt the multi-trillion dollar insurance industry.

By recognising the power of personal data, FF and Sherpa are creating a product that completely reimagines our relationship with data and insurance alike—a forward-thinking vision that drives Sherpa’s product development every step of the way. Data, and the importance of who owns and extracts value from data, is a cause that is close to my heart.

FF is proud to have also supported the launch of Vero, the #1 app on the Apple store, a social platform described as the antidote to Facebook.

different countries
Read Bio
Chris Kaye

I love insurance. Wow, that’s good to get out into the open. Not a popular opening gambit at a dinner party, granted. But, sadly, true. It is important. It helps people achieves their dreams, and protects them against their nightmares.

But I hate what insurance has become. Mis-trusted, confusing, complex. I am ashamed to read in the paper that an insurer has wriggled out of its commitment to pay a claim. Or has tried to gouge someone on renewal. Or has mis-sold someone something they didn’t need (PPI, anyone).

So, I tried to think about how to bring insurance back to what it is there for. Supporting people in times of need.  And I tried to bring together a team of people who shared this passion - click around this page for some of their personal stories. Together, we have come up with some fundamental ideas that power Sherpa, and that make it different from what traditional insurance has become.

The idea of a subscription model, rather than commissions - so we don’t make more money by flogging you more insurance. The idea of a Brain and Score - to help you understand what insurance you need. The idea of an insurance account, rather than individual policies - so that your insurance can change and stay relevant as your life changes. The idea of cutting out the middlemen - so that more of your money goes towards paying claims.

They say that the best problems to solve are the ones you face yourselves. Starting Sherpa meant leaving the comfortable, safe world of corporate life.  It took me over 20 hours to sort all my insurance out as a newly self-employed person.  So, I am so proud that the first incarnation of Sherpa is helping people like me - the entrepreneurs, the freelancers, the contractors of the world, who seem to have been forgotten by traditional Sherpa.

Read Bio
Technology Advisor
Darren Price

My personal reasons for joining Sherpa were initially the quality of individuals involved within the organisation. This has been confirmed as I've become more engaged with the business.

The proposition is not only unique but can be a true market disruptor going forward. To be involved in such an exciting customer proposition working with a very talented team is my main motivation.

I am an award winning FTSE 100 Group CIO/COO; I bring a wealth of IT and Operations experience to the organisation, predominantly from a Financial Services and Manufacturing background having previously held senior leader roles at RSA Group, GE and Unilever.

Read Bio
Remote Executive Assistant
Diana Manlulu

I'm an online executive assistant, which means managing the calendars as well as flight and hotel bookings for employees. I also act as a bookkeeper for Sherpa, logging in invoices and receipts, the monthly payslips and processing the monthly FS5 Revenue and HM Revenue.

I graduated from Holy Cross of Davao College with the course in Business Management. I have been working as an online executive assistant for seven years and before that, a call center agent for seven years.

Technology Advisor
Fergus Doyle

I have a background in building and scaling technology businesses from inception to exit across Europe and America. My experience in building tools for the freelance economy stems from my time at Kalo where I helped the company scale from pre-launch to being backed by some of the biggest names across Silicon Valley and London. This experience helped me understand the need for tailored technology solutions to support the continued trend around freelance and flexible working, which Sherpa addresses directly.

Joining the Sherpa team as a technology advisor, I help support Sherpa's technology and operations teams in their ability to scale to meet the significant demand for the Sherpa product generated since their launch.

Gareth Thomas

Its hard not to be inspired by the story behind Sherpa when you first meet Chris our CEO. I had left my previous company Fuel3D as CIO at the end of 2017 and had filled in with a number of interim roles looking for just the right opportunity and the right team to execute to work with, I hadn’t then also expected to be inspired by a story about insurance but I certainly was at that lunch meeting.

Gareth Thomas has more than 25 years of technology expertise. Before joining Sherpa he was CIO at Fuel3D managing development of their BioVolume software in partnership with AstraZeneca, their 3D image cloud processing platform and desktop software application suite. Prior to that he was CTO at Larosco building their revolutionary social referral and recommendation platform for recruitment. In 2005 he was made Director of Engineering at pioneering social network and lifestyle portal aSmallWorld where he oversaw initial growth from launch to over half a million members.

Prior to 2005 he was based in California for twelve years during which time he was Engineering Manager at the Medwell Group which developed EMR systems for physician practices and pioneered early hand writing applications for doctor notes. In 1996 he co-founded Mercury Software as a technology consultancy which included such prestigious clients as Hitachi Data Systems, Toshiba and Philips. During this time he also co-founded Castell Technology that developed an enterprise portal technology and partnered with Northgate Information Systems to deliver this product to their clients in Europe.

Graham Handy

I am a former EY partner, and have operated across the global insurance industry for over 20 years advising on financial, operational and strategic challenges.

As Global Insurance Customer and Growth leader at EY I have for many years now been advocating a shift in the way the insurance industry engages with its customers, and I support Sherpa as an advisor and investor because I believe this team has the potential to make that shift real.

I am also Chairman of the Fundraising Board of Sense - the deaf blind charity - and a Fellow of the Institute of Actuaries.

and working in
different locations
Greg McCafferty

I was originally a lawyer, then a banker and am now in insurance. As my wife often says, it's not the coolest career path in the world. But with Sherpa, I get to help build our own business from the ground up, and solve real problems for real people rather than push paper around. I think that's pretty cool.

If I am honest as a consumer of insurance, the less time I spend thinking about it, the better. It's just not fun. Insurance should operate in the background. It should just happen. It should just work. So I can forget about it.

I think that's the driving force behind Sherpa. Build something that just works. And works for me, not for the insurance industry. So take away all the bad things - multiple different policies, tracking renewals, worrying whether I have the right cover, worrying whether a claim will be paid, worrying about paying too much - and instead get proper advice on what I need, have that delivered to me once, have it change when my life changes, and don't let it cost me the world. It's that simple.

Ioannis Loukeris

In theory I am a Senior Software Developer here at Sherpa, but this title is not accurate for various reasons... First of all the Senior thing .. Senior is not for the position but for the age, I am by far the oldest in the development team... And the "developer" thing is a bit off too, as far as the method is concerned: I am the resident whiner of Sherpa. I stick my nose in everyone's business and start whining about everything.

In the end, issues are identified and fixed, and everyone is happier. Therefore the Software thing is not quite accurate too. You see, I mostly stick my nose and whine in other people's non-software things... On my spare time I write back-end code too, or is it the other way around?

Jane Hodges

I’m a Chartered Financial Planner who has been involved in all aspects of the provision of financial advice for nearly 30 years and still manage to keep the same passion for delivering the best advice and helping individuals make the most of their finances. I’ve set up several independent businesses, and currently run my own financial advice practice but also run sub-businesses providing paraplanning services and consultancy services to innovative advice businesses trying to harness the power of technology to give great advice, easily and simply.

I’ve been involved in all aspects of the provision of advice including using technology, working in compliance, dealing with complaints, liaising with the Regulator, trained and supervised other advisors. I’ve been a Compliance Director and worked on numerous projects including ‘Treating Customers Fairly’ and the recent Retail Distribution Review that changed the way the industry gives advice.

So my experience is extensive and my aim is to ensure all of that knowledge gained is used to provide the best advice service possible and to help others in the profession to do the same. I’m very pleased to be able to help Sherpa on its journey to enhance the accessibility and understanding of protection needs for those who need it the most - the self-employed.

Member Services Agent
Jawad Khan

I have an extensive Customer Support background within some challenging industries find it easy to identify with what Sherpa is trying to achieve.

Putting Members first with a transparent and commission free product as well as placing the utmost importance to the member experience throughout their journey with us.

I hope to give an honest and informative experience to all of our members and continue looking for ways to improve our interactions.

Data Scientist
Jeremy Tua

Data and Risk Analyst responsible for the personal risk estimation engine, with a side of supporting the product and development team.

When not crunching the numbers, you'll likely find me in the studio making teapots. I rank at the 27th percentile for height in Europe, which means there's a 73% chance you're taller than me.

Advisory Board Member
Julian Buhagiar

I’m an investor and an advisor in Sherpa. I have a PhD in data mining and have been CEO and CIO to various corporations in gaming, fintech and music markets.

Insure-tech is rebooting a draconian vertical, and wholly revolutionising the financial industry; from an investment standpoint it’s a great space to be in. If you could couple that with an accessible consumer product and provide intuitive access to one of the most fundamental services today, then you have your next unicorn. Sherpa is that company.

Lachie Gillies

I come from over 15 years’ experience in financial services technology and operations. I have been trusted by global investment banks to manage their infrastructure, compliance and operations, and was most recently a Director at Deutsche Bank, and head of Asia Technology Ops. I was the CTO for a successful hedge fund, Artradis, buying, building and managing the technology required for a multi-billion dollar fund.

I couldn't resist the idea of Sherpa because I realised there were few things I spent more on but understood less than insurance - and solving my own as well as others' frustrations has become my passion.

Technology Lead
Lincoln Grixti

I joined Sherpa as employee number one a few years back tasked with being the resident technologist.

I spend my days guiding my team to build the next cool thing at Sherpa, and planning the next 15.

When I’m not at the office you’ll either find me working on my home renovations or volunteering with various charities.

Member Service Agent
Lorna Law Dickson

I have an extensive financial services and insurance background and this makes me appreciate even more the the innovation that Sherpa is bringing to the market place.

I look forward to being part of a team committed to helping the self employed as I have been a self employed contractor myself so appreciate the challenges it brings.

Advisory Board Member
Neal Kissel

On a bright spring day, while walking with a dear old friend, the question turned to insurance and why the industry was struggling to help customers answer some very basis but important questions. Those questions; boiled down to the simple ones … “how much insurance do I need”? What kind of insurance? And when do I need it? I have worked in the industry for 20 years these simple questions are hard to answer, and often answer incorrectly. The friends was Chris Kaye … Creating an insurance company that was truly focused on helping customers build risk portfolio’s instead of just selling products was something I fundamentally saw a need for, and something I believe in deeply.

Most people I know are fundamentally over-insured in many ways, but also under-insured on key risk as well. Having 15 different travel insurance policies seems wasteful, but not having any personal liability insurance seems a bit naive, especially if you have a rental property. Paying a lot of premiums for life insurance for your spouse that doesn’t work or have an income would seems to be a questionable use of hard earned funds. Delivering value to the customer has start with helping them understand their true needs; helping them understand value and benefits of risk protection when its needed, and not wasting money on when it is not..

Chris Kaye and the team at Sherpa share a vision, I believe in and am honoured to be a part of. It will need to build step by step, but the north star is a bright one; and as long as we stay focus on delivering value to the customer we will be successful in simplifying and helping customers protect the things they value most at the right time, in the right way, in the most efficient and effective means possible.

The world is moving fast, and insurance will never move as slow as its moving today, I want to be part of helping shape the future...

Patrick Muir

I got into Marketing because I love building things and I love connecting customers to things that they genuinely love. That’s a whole lotta love. I was lucky enough to be part of building two really customer focused businesses that became really successful but for the past few years I have been working independently helping businesses develop their proposition, brands and marketing.

That is until Sherpa and I bumped into each other. From the moment Chris explained the problem and how he was hoping to solve it I was sold. Taking a 200 year old industry and bringing it bang up to date and by so doing delivering something really great and useful for the customer, what’s not to get excited about. In particular I loved the separation of the product price from how we get paid. We charge a separate membership fee and not commission. Commission has been responsible for a lot of bad things recently. Basically, if you are dealing with someone who is getting paid on commission you know they have only 1 objective, to get you sold. Being a membership organisation means we can genuinely serve our customers and give them what they need. More cover or less, we don’t mind. We hope the result of this will be happier and more loyal members.

So I stopped working for lots of different companies and started working for Sherpa. Bringing my experience of building businesses together with the desire to take the latest marketing thinking and use it to bring the right customers to our front door and build a great brand was too good a brief to pass up.

As I said to Chris at the time, “There are only two challenges with building Sherpa, building the service as he described and then communicating it effectively to the right customers”. We’ll leave you to be the judges of how we do.

Reinsurance Expert
Paul Hately

I worked in the engine room and factories of the life insurance protection industry for over 30 years and was always looking for ways to reduce frictional costs and provide customers with more cover for their money or charge them less for the cover they needed.

Sherpa provides a solution to this by enabling customers to get cost effective advice about their risks and what insurance products will cover those risks - this is the cool, clever and for the customer low cost Sherpa brain. Sherpa then provides insurance at as close to factory gate prices as possible.

It’s also a great passionate team.

Head of Insurance Proposition
Sara Cobbett

I took a leap of faith into early in 2017 when I left the relative security and stability of the corporate world and joined what was for me the completely alien world of self employed contracting. Working for myself was initially both scary and exciting; the worry of finding the next contract - countered by the freedom of working hours to suit my family life and reduced travel into the city.

Having spent most of my career in financial services, and more latterly insurance; I was extremely aware of the increased risks I had taken on: No ‘death in service benefit’ meant I should take out more life cover and no ‘sick pay’ meant I was extremely conscious that any ill health could have a devastating impact on my ability to support my family. As a result of some networking and a number of random events aligning (often the way in the world of contracting) I started to support Sherpa as they created the solution to many of the challenges I was personally facing  - and was hooked by the energy and creativity of being part of a team that was creating something that could really make a difference to real people.

Now a permanent member of the team I’m responsible for developing bespoke insurance products that will flex as customers’ needs change over time. I also lead the team of customer service agents who are committed to providing an exceptional level of support to our customers. Outside of the ‘office’ I’m Mum to two teenagers so have a number of roles including: football manager; A’ level coach; housekeeper; gardener; career advisor; event planner; and romance counsellor!

Head of Product
Simon Azzopardi

I am not an insurance person. Winter of 2016, I was on the hunt for the next big project, travelling to Europe's top startup hubs and being exposed to some very interesting concepts. However, I wanted something that was different in terms of its human impact where the problem was so real, it just had to be solved. And that is when I met Chris. Over coffee, we spoke about the problem in insurance, with Chris breaking it down in a way that for the first time, made it comprehensible. I was not in the insurance industry and always thought it was that necessary evil type product. And when I saw insurance startups, I always found them to be simply the digitisation of the same problem, hardly solving it.

"The problem with insurance is the insurance product itself". And "We need to insure people not buckets of risks they call products." The conversation sparked curiosity and I started researching both the products on the market as well as customer reactions to them. It was clear that the problem was real. Insurance products suffer from feature soup, with risks (think of them as features) being thrown in to the mix making it seem more valuable. The more features an insurance product has, the more complex it becomes, with the value added not necessarily needed. The result is the customer buying something they don't understand, paying for features they may not need, resulting in the most painful experience possible. What about the post purchase experience? Well, if customer's don't know what they are being sold, the post purchase experience is bound to be terrible. 

What Sherpa has set out to do is to transform the industry by creating protection a customer needs, supporting the customer throughout the process, and constantly being on the customers' side. Sherpa is about moving from feature soup to giving customers only the protection they need; from an unfair commission based business model relying on hard-sales to a flat subscription service, from complexity that only the risk geek understands to democratised versions of protection. The future of everything is exciting as long as it evolves and insurance will be positively impacted to benefit customers the world over. We have started with one of the most under-served customers in the U.K., the self-employed, and will continue to make Sherpa protection easier, simpler and relevant for more people after that. I am still not an insurance person, but a person making insurance simple.

Advisory Board Member
Simon Lee

I was in banking for much of my career, holding a number of senior positions in the NatWest Group. In 2003 I moved into insurance, ending up as the Group CEO of RSA, a FTSE 100 insurer.

I am now in a different stage of my career, where I can choose a number of different places to spend my time. I am a Global Advisor to Fairfax Financial (a large reinsurer), and am on the board of a number of insurance and technology businesses.

I have long held the view that the insurance industry is not as dynamic and customer focused as it should be. The opportunity to associate myself with a group of highly focused and smart entrepreneurs, seeking to disrupt the insurance landscape, was simply too tempting to resist and so I find myself on the Advisory Board of Sherpa!

Partnerships Lead
Stephen Gazzard

I manage partnerships for Sherpa, trying to find like-minded businesses we can build relationships with.

Having worked in Financial Services for over 30 years I know how much change is needed to really help people get their financial lives in order; Sherpa were attractive to me as they have a grand vision for helping consumers understand and manage their personal risk, and genuinely want to help with useful advice and flexible products.

When I’m not working I spend time with my wife, walking our Labrador and drinking red wine, and coaching, watching and refereeing rugby.

Xabier Rivera

“I think, therefore I design”

I'm a thinker in the free time, a doer at work time. I'm constantly thinking about how to improve everything around me, willing that my time spent thinking about how to improve something will save time from every user of that product.

Every well-designed product excites my brain and that’s what I want to do with Sherpa, create excitement and improve people’s lives.