Successful Insurance Innovation

Jason Stockwood, Vice Chairman of Simply Business, shares his thoughts on the equation for successful insurance innovation with David Schapiro, Co-Founder of Planck.

Interviewer’s notes:

I have known Jason for many years as a serially successful CEO and entrepreneur with a sincere customer and employee-focused attitude.

In his journey with Simply Business, he transformed a small insurance business into a big one, creating value for his shareholders, customers, and employees, but this is the first time I have discussed with Jason the potential opportunity incumbent insurers have in the new world of insurance.

David Schapiro (DS): Could you please tell us a bit about your background and share with us some of the highlights of the Simply Business journey?

Jason Stockwood (JS): I’ve often described myself as a sort of accidental businessman, and what I mean by that is that I’ve basically spent my career doing stuff that I’m passionate about and interested in.

In more recent years, that’s manifested itself in technology – and our relationship with it – but you can probably trace this inclination to following my interests right back to my childhood.

Growing up on a council social housing in the north of England, there was very little pressure to be successful. But this was massively liberating – it meant I could follow my curiosities and interests.

After finishing formal education in the UK, I won a scholarship to high school in the US for a year, spent my time on a kibbutz in Israel, worked at Disney World in Florida, and was even a holiday representative in Greece. There was no end goal as such, I just found each of those things interesting.

Eventually I found my way back to education, via my passion for reading and especially philosophy. Thankfully, it was 1992 – the last year you could get a mature student grant – so I ended up studying in Bolton. To this day I still think that my degree helped to shape the way I think about the things that interest me.

Soon after, my curiosity turned to technology and the internet. I spent eight years at, working on some truly groundbreaking stuff and in a way that was alien at that time – driven by tech, open-plan offices. The sort of thing that’s commonplace today, and especially at Simply Business.

When I look back at the Simply Business journey over the last 10 years or so, it’s been remarkable and is a real source of pride.

We’ve transformed the way small business owners purchase insurance, doing incredible things with tech and data at the core. But the thing that always excites me most isn’t necessarily what we’ve done, but how we’ve done it.

Our culture’s unique and it’s built on values and principles that I wholeheartedly believe in – like trust, authenticity, and experimentation.

Meanwhile, we’ve always made a huge effort to put our people first. Whether that means introducing flexible ways of working, or ensuring everyone benefited financially from our acquisitions, people have always been a priority.

Being voted the Best Company to Work For, twice, was special, as I’ve always wanted to build and be a part of businesses where people felt valued. Equally, becoming B Corp certified (a business that balances purpose and profit) was a vindication of our efforts to create a company that has a positive impact on the world at large.

DS: Looking back at this decade-long journey, what are the key insights and/or lessons learned that you could share with us?

JS: Think about your culture and your people beyond anything else.

The aim is to build a culture that values learning and experimentation, and gives people the freedom to make mistakes and grow.

It’s about making life at your business as good as it can be for every team member. Practical measures such as flexible working and annual pay rises should be coupled with intellectual stimulation and work that aligns with people’s passions and interests.

Fundamentally, the challenge is to hire fantastic people and create a culture that lets them thrive. After that, it’s your job to set a clear vision and strategy, before getting out of the way.

DS: Has the rapid progression of technology over these years influenced your insights?

JS: Firstly, the tech landscape has changed enormously over the last 10 years.

Technology itself has evolved immeasurably, and everything from engineering talent to customer expectations have evolved with it. But unlike 10 years ago, tech is no longer the “hard” bit of running a business, certainly not in the sort of fields we operate, like ecommerce.

There are still technological challenges, of course, but the real challenge is nailing the culture. Creating a culture of trust and experimentation – that delivers – is more difficult than the tech itself.
And technology can actually have an adverse effect on culture – at its worst, it can downgrade the best of what makes us human.

That’s why at Simply Business, we place such an emphasis on human interaction. Mobile phones are banned from meetings, and tech is only used to connect, not distract.
Leaders need to think seriously about how technology can impact on people’s productivity, happiness, and output. And we need to constantly remind ourselves that technology is a tool, and by no means a replacement for human imagination.

DS: Insurance is a regulated business, with regulations differing to different degrees across countries. You have experienced regulation in the UK and US – has this influenced your insights?

JS: Innovating in any highly regulated industry is a challenge, and we’ve seen that across both UK and US insurance markets.

Complex regulation is a huge barrier to entry, technically. But part of the challenge is that regulation isn’t usually the sort of stuff that gets people out of bed in the morning.
It’s essential to hire people who understand the regulation, but are open and enthusiastic about innovation and finding solutions.

DS: Data is a key asset in insurance – how does this tie into your insights?

JS: There has been a lot of noise about “big data” in the last 10 years and people who believe there is an external panacea that will create value for your customers. This may or may not be true but at SB we are interested in external data, but we are mostly focused on the unique internal data from relationships we have with our customers. All of this is in service of creating superior experiences and products.

DS: How do you see these insights influencing the players – incumbents and newcomers – in the evolving world of commercial insurance?

JS: As previously stated, I am not convinced that technology is the hard piece anymore. In my mind, there are three things that help massively: access to smart people with a culture of experimentation, access to capital, and long-term perspectives.

And in this regard, insurance industry incumbents have a huge opportunity and possibly an advantage over newcomers to the industry.

DS: Could you please elaborate on this opportunity and potential advantage for the insurance industry incumbents?

JS: Put simply, the best incumbents understand the need to innovate as an existential requirement in a way that leaders in another era did not. Marshalling resources, people, and capital towards this endeavor is no longer a luxury, but a requirement. Add into that mix the advantage of a deep understanding of regulation plus customer loyalty/apathy, then I am not convinced the challenge is the same as other industries where the barriers are lower.

DS: How does the customer and our relationship with the customer play into all of this?

JS: Customers have never had more choice, nor have they ever been so demanding of a simple, seamless experience.

It’s a prerequisite of successful businesses these days to harness the power of data and technology to match customer expectations. And a customer-focused culture is paramount – where the goal starts with building solutions to customer problems.

DS: There appears to be a cultural difference between the tech industry, which often strives for rapid disruption, and the insurance industry, which is based on longevity. Do you agree? And if so, how does it influence your thoughts on successful insurance innovation?

JS: To successfully innovate in an industry as complex as insurance, I believe you need three key ingredients. Firstly, you need access to technology and an experimental customer-focused culture – something which you see in all great tech firms but is probably the hardest of the three things ingredients to get right. Secondly, you need a deep understanding of the insurance industry itself. Finally, access to capital is a huge advantage.

DS: What kind of company culture do we need to be successful in the new world of insurance?

JS: You need to create a culture built on trust, where great people are given the conditions and freedom to test hypotheses. And it’s important that people have fun while they’re doing it. I’ve always wanted to build the sort of business that I’d want to work in, and a team of happy, motivated people is the single greatest element to success in business.

And everyone should do well out of the business’s success, not just shareholders.

Equally, businesses need to value people and society alongside profit – more and more businesses are realizing that they have a duty to be a force for good.

The new world of insurance, and the technology that comes with it, should unlock new ways of working that make people’s lives better. New technologies will fundamentally change the way businesses operate, and it’s our duty to explore these and understand how we can use this to make people’s lives more fulfilled.

Jason Stockwood – Bio:

Responsible for developing Simply Business, Jason sets the challenge for defying the insurance company stereotype. From technology and data science to customer experience and people engagement, Jason has spearheaded the company’s mission to create something better.

Jason joined Simply Business from the global dating website, where he was International Managing Director. He’s also spent time as Managing Director at Travelocity Business and held roles at Trailfinders,, Skyscanner, and The Drinkaware Trust.

In 2016, Jason won overall Best Leader at the Sunday Times Best Companies to Work For awards, completing Simply Business’s Best Companies hat-trick. Simply Business had already picked up the Best Company to Work For award two years running.

As CEO, Jason led the successful acquisition of Simply Business by Travelers in 2017, before stepping into his current role as Vice Chairman, where he works closely with the Travelers executive team on innovation. Jason is also a trustee of B Corp UK – a growing community of businesses who balance purpose with profit.

In September 2018, Jason authored his first book, Reboot: A Blueprint for Happy, Human Business in the Digital Age, detailing how organizations can think differently about technology – using it to empower teams, fuel creativity, and make people happier. And more recently, he co-founded 53° Capital, a private capital investment firm with a social conscience.


Check out our next CEO Series interview with Ari Chester, partner at McKinsey & Company, where he discusses the sources of disruptive innovation in commercial insurance.

Related Articles

We use cookies to provide the services and features offered on our website, and to improve our user experience. Learn more