February 7, 2022

Leading a Business with Jason Stockwood

Matthew Birchall

There is no doubting that we live in a digital age. From online dating to Pokemon Go, the world is evermore seen through the lens of a screen. The expansion of the digital realm, however, has been uneven: some were quick to recognise the potential of the internet, others were sluggish to make a start.

Insurance, that most vital and traditional of industries, has yet to fully embrace technology. But this does not preclude the existence of outliers: Jason Stockwood, the CEO of Simply Business, the UK’s largest provider of business insurance and the winner of the Sunday Times’ Best Company of the Year Award two years running, has been bucking the trend in style.

With plans to launch in the US later this year, we thought it was the perfect time to catch up with Jason to talk about the culture of Simply Business, his journey from a single-parent house to CEO and his thoughts on learning and hiring at Simply Business.

Jason’s key learning takeaways:

  • Strive for a culture of collective improvement each year. There’s no such thing as work/life balance – it’s just life. So ask yourself, “How can you make your company better for every team member, every year?” Incremental, gradual improvement is the key.
  • Make sure your team feels valued. This means taking practical measures such as annual pay increases and the promotion of flexible working hours.
  • Vision and culture is the key to recruitment. Get this right and hiring is a lot easier. The real challenge is finding candidates with “X-factor.” Does the applicant excite you? It’s about more than technical skill.
  • The most valuable people are curious, inquisitive and unafraid to self-teach themselves new skills. Who in your team goes that little bit further? Who in your team puts in discretionary effort without expecting an immediate reward? These are the people you can invest your trust in.

How did you arrive at Simply Business?

I got involved with the internet in its early days, so I was able to capitalise on some good timing. After being part of the team trying to change the world of travel with lastminute.com I turned to online dating. Like many people I had tried it but not always successfully: I thought there was a better way, so I got involved in this space to help people find love through match.com.

Both these businesses successfully exited, meaning that I had to ask myself yet again what I wanted to do. What else was I unhappy within the world? What problem could I help solve?

Insurance quickly became my focus as its the worst of all possible worlds for the customer. People either don’t understand it or they don’t like it. I wanted to change this by creating something better.

And this is where Simply Business comes in. It had already started, but it was trying to be a portal for everything to do with small businesses: it sold mortgages, advised on lending policies and offered invoice financing services – insurance was just one of the many things it did.

Yet the real problem with the business lay in its profitability: it was about six million pounds in debt and loss making. To combat this we decided to strip the business down, sell assets and laser in on the insurance market. It was a classic case of simplifying things to prove that we had an economic model that worked.

What makes Simply Business the best Company to work for in the UK?

The awards are a nice validation for what we do on a day-to-day basis, especially since it’s an employee voted award. But we obviously don’t come into the office every day claiming that Simply Business is the best place to work in the UK!

On joining the company six years ago I made a commitment to improve the business for everyone on the team every year, no excuses. It’s a commitment that I take really seriously. As well as doing stuff that is economically profitable and good for customers, it’s important to look after your team. But what does this mean in practice?

“We do a lot of practical things each year to make Simply Business a place where people want to work. This ranges from annual pay increases and clear bonus structures through to the adoption and encouragement of remote / flexible working.”

Tech is also banned from meetings unless you absolutely need it for a specific purpose, such as recording or presenting. We want people to engage with one another. It’s about being present and building relationships with people, not immersing yourself in a screen.

The same applies when you go on holiday! We tell our team it’s OK to put an out of office note up saying you won’t see the message. I’d rather my employees spend their break doing what they want to, safe in the knowledge that they’re not going to be bombarded with messages when they get back. So it’s about making sure your team knows they’re valued and that their life outside work is as important, if not more important, than what they do during the week.

What qualities do you look for when hiring?

Getting the right people on the bus is half the challenge of building a great business. In my first year with the business we actually changed 53% of our team, principally because we wanted to shift gears and drive ourselves forward.

Technical expertise is a given, regardless of where you are in your career. Whether you’re someone looking to apply for an entry-level position or you have a proven track-record, know-how and intellect is assumed.

In all honesty, however, we don’t have to work too hard to find candidates who have the core skills to do the job. That’s one of the benefits of living in a great city like London or Northampton: there’s an abundance of talent. If you have the right culture and business vision, applicants will flock to you.

The real magic lies in finding people with an attitude and mindset that fits your culture. Our values are clear, and we want people who connect with them. At the end of every interview we ask our team, “Are you excited to work with this person?” If they say no then we don’t hire them, simple as that.

And what’s the key to progression? What makes people stand out?

The best people are the people that don’t need managing. It makes my role so much easier when people take the initiative to get things done, because it allows me to focus my efforts on coaching and mentoring. People who ask for forgiveness rather than permission and people who just get on with the job are always at the top of my list. Discretionary effort goes a long way in any walk of life.

A dose of humility is a winner too. The two senior hires I’ve just made embody this: when they don’t know the answer they put their hands up and ask for help. In my experience people tend to coalesce around leaders who aren’t afraid to show a human side, a touch of vulnerability.

In terms of your own career, what skills have allowed you to excel? And what role has your background played here?

I’ve always been naturally inquisitive and curious about how things work, and this is largely why I decided to do a Philosophy degree. Asking questions and working towards answers is built into my DNA. How can we make things better? That’s been a big question for me, whether that’s at lastminute.com, Simply Business, or in my personal life.

“My attitude is inseparable from my childhood. It’s safe to say that I didn’t have a great start on paper: I grew up in a single-mother household, never knew my dad, was working class, and had no money at all.”

But the upside to this was that my mum was always working so I had a lot of freedom to do what I found interesting: I had no boundaries and lots of independence. In hindsight that’s been an incredible privilege, as my Mum was a great role model for hard work and tolerance. There was obviously potential for this to go wrong, but I’ve always been committed and self-motivated, so it didn’t end too badly!

Later on in life, when I was in my twenties, I discovered literature and began to self-educate. When I traced the primary sources in the literature I was reading it seemed to all lead back to philosophy, so I went and did a Philosophy degree at Bolton. This gave me the intellectual tools to start learning properly for the first time in my life.

And it’s something I continue to do to this day. Next week, for example, I’m on holiday and I’ve got about seven books lined up on my bedside table to go through! The more you learn, the more opportunities you have to do things that excite and challenge you, so I never think of education as a finite thing.

But to go back to the original question, I think that resilience has been key for me. If you’re doing something that doesn’t have a blueprint then you need to be able to deal with stress and setbacks. You need that classic entrepreneurial spirit, where everything is solvable and has an upside.

Who do you find inspiring in your network?

Every month I get together with a cohort of business leaders called the YPO (Young Presidents Organisation) to discuss business challenges and the world around us. It’s like the Masons meets AA! Having a network of other CEOs who have done similar things to me is always great for perspective. I’m not interested in people who have just made money. For me, it’s about how you do it, so I’m inspired by people, from all walks of life, who have a strong value system and a desire to affect change in their life.

But who drives me on everyday? That would have to be Chris Slater, my COO. He’s simply the best man I’ve worked with, and he makes me want to be better at my job. He works harder than anyone I know: I’ve come into the office at 0630am before and he’s already there mid-flow. His attitude for getting things done never ceases to impress me.

What’s been your best learning experience?

Singularity University hands down. Individual books and courses have been useful throughout my career, but they haven’t had the lasting impact that Singularity has had. As a single, finite experience it was profound; I went there a few years ago and learnt about subjects as diverse as exponential technology, biotechnology, and robotics. Even though it was just a week-long course it was a huge catalyst for me to go off and learn about new subjects, new ways of thinking.

This October I’m off to Harvard to do a short course on behavioural economics. My aim is to do a formal course every two years, alongside the usual self-directed learning that I do. While I’ve done some great online courses, such as Coursera’s behavioural science course and Decoded’s learn to code in a day course, I tend to prefer immersive experiences which I can then apply to my work when I come back.

What would you include on your learning playlist?

DLD conference  are easily the best conferences I go to. Their outward looking, multidisciplinary approach really chimes with my own belief in what a conference should do. In terms of video and online content, Ted Talks and podcasts are phenomenal learning resources, especially since you can soak up short bursts of inspiration wherever and whenever you like. That’s the definition of portable power. I recently watched Susan Cain’s talk on the Power of Introverts, for instance, and that was a real handbrake in terms of how I thought about company culture at Simply Business.

Over the last twenty years, in the ecommerce sector at least, we’ve moved towards agile and collaborative workspaces and business models, with the unintended consequence that we’ve tended to overlook the opinions of quieter types, the very people who are often the most creative and thoughtful. I actually read this when we were designing our offices, so I decided to put in more private spaces to make sure my whole team felt comfortable.

The Clue Train Manifesto  is a book I read years ago, but one that deeply affected me. It predicted how working cultures, on both the employee and customer side of the equation, would be forced to change if they were going to keep up in the digital age. It contains lots of really substantial intellectual ideas around the potential of the internet, yet it’s written with great humour and a sense of style.

Novels, I think, are just as important as business books, because they make you think hard about what sort of life you want to lead. I always find myself applying the learnings I take from novels to how I approach managing people. Fugitive Pieces by Anne Michaels, for example, is a book that I absolutely love and there’s so much in there about being human that you can learn from. I’m also an avid reader of Wired Magazine and MIT Technology Review. These are consistent week-in, week-out reads for me, and I always have an active subscription.

In short

It seems fitting that Jason Stockwood is in charge of a company called Simply Business. His no-nonsense approach to leadership is all about focusing on essentials, on what matters most: delivering a great service to customers. Yet it is the culture of trust – in people and their potential – that most impresses this interviewer.

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