Ashley Baxter’s route into digital certainly wasn’t a traditional one. Discover how she taught herself how to build websites, and developed her digital marketing skills as founder of With Jack in our latest #wheredidyoustart story.

My career and route into digital happened by accident. I wanted to be a musician. Drumming was my passion. I studied a practical music course for two years and played in a band outside of college.

Just as my two years at college came to an end, my Dad passed away and left his insurance business to me. I was 18 at the time. I knew nothing about running a business and even less about insurance.

I didn't realise it then, but this would be my route into digital and the start of an interesting journey! What followed was an intense period of learning how to build websites, internet marketing and other digital skills. While I didn't fall in love with insurance, I enjoyed building websites and seeing customers interact with them.

I didn't realise it then, but this would be my route into digital and the start of an interesting journey!

I threw myself into the web industry; attending conferences, following designers and developers on Twitter, reading web-related magazines. It was through being exposed to the talent in that industry that it hit home just how much design and technology in the insurance industry sucked.

To most insurers it was an afterthought and something they invested little money into. 74% of insurance companies see technological innovation as a challenge, but few are developing their own offerings in-house or partnering with startups.

While things are getting better, I felt like the insurance industry was trailing behind in terms of technology and the web.

I decided to focus on improving design and technology in the insurance industry, in any small way I could. The bread and butter of an insurer's website is their quote system. It's an integral part of the customer journey and usually the reason someone visits your site.

While things are getting better, I felt like the insurance industry was trailing behind in terms of technology and the web.

I learned enough Ruby on Rails to build a prototype of a quote system. This was 2012, and responsive design was just gaining traction, so I knew it would be some time before insurers jumped on the bandwagon. I focused on building a quote system that would work across all devices.

I'm based in Glasgow, but I flew to London to demo my prototype to an insurer. They loved it and that kick-started my goal of marrying my interest in design and technology with my career in insurance.

Whilst that opportunity never panned out, I didn’t want to give up. My dad's business never felt like something I could experiment and be creative with, so I started my own project.

In September 2016, after 2 years of trying to find an insurer to partner with, I launched With Jack. With Jack is aimed at providing freelancers with insurance that helps them financially and legally if they have problems with a client.

My focus was on creating a better customer journey. Instead of filling out a traditional proposal form, you'll have a chat with Jack. His questions change depending on your answers. The idea is you're never asked something that isn't relevant to the work you do, meaning you get your insurance quicker and with less hassle.

I've bootstrapped With Jack with money I've earned photographing weddings at the weekend, so growth is slow but steady. 40% of freelancers who get a quote become customers, and I’ve retained 87% of customers come renewal.

24.Ashley Baxter (2).jpeg

With a team of freelancers, we’re currently building version 2 where quotes are automated. This will give us more scope to be creative with the customer journey. It also means I won't be glued to my laptop having to manually process quotes. Fun fact: the strangest place I've processed a quote was on top of a volcano in Spain!

Day-to-day I focus on iterating on the customer journey. Learning from the first 300+ customers we've signed up is crucial, as well as the ones that choose not to use With Jack. Customer development is my priority and an aspect of building my own company I really enjoy.

I used to have ideas and impulsively act on them. Now I make sure I speak to my customers first and validate features before we build anything.

Something else happened on this journey that I didn't expect to. I developed a love for insurance! Seeing how many freelancers we've helped in scary situations - and the fact they may not have been insured if it wasn't for building With Jack - spurs me on.

When circumstances took me away from my career in music and over to insurance, I initially felt I had let myself down. I had a clear path of how I wanted my career to look, and this was a detour. Looking back, I’m glad I let myself explore new opportunities and remain open-minded. Although I didn’t realise it at the time, that’s what led to building With Jack.

Everyone measures success differently, but to me it’s being able to crawl into bed at the end of the day feeling creatively satisfied and challenged. My job makes me feel that way.

I'd encourage others to embrace the unconventional routes into digital. Not everybody is suited to attending university or college. In digital, there's no traditional path like other industries and that's what I like about it. If it interests you, there's little barrier to entry. Get learning, get stuck in and just go for it!

Have a story to tell that will inspire others to get into digital? Get in touch at [email protected]

she does digital

she does digital @shedoesdigital

We're a collective based in Leeds who want to highlight the opportunities and careers available to encourage women to join the digital industry.