Freelancers, With Jack has got your back
Freelancing is witnessing an increase in adoption as people value freedom and control over their lives while earning a living. It is predicted that freelancers will make up the majority of the U.S. workforce within a decade. The shift to freelancing brings with it problems like non-payment and legal proceedings for errors committed. Insurance, in general, is a good option to indemnify losses that freelancers may incur. However, the complexity of the insurance industry has kept many away from it.
Ashley Baxter, an aspiring musician, was studying drumming at college and had plans to enter the music industry. At the age of 18, she unexpectedly inherited the family insurance business and this laid the foundation for With Jack — a bespoke insurance provider for freelance creatives. She zeroed in on the freelancing sector because of the lack of trust in insurance providers, limited usage of technology by insurance companies, and the boring user experience while buying insurance.
“Those problems excited me and I wondered if I could create a business people could trust, with great design and technology at its core.”
Though she has basic programming knowledge, Ashley worked with a team of developers and designers in building the platform. With Jack was launched in September 2016 as a side-project but since the beginning of this year, Ashley works full-time on the business.
“Insurance is a regulated industry, so it can be difficult validating ideas. There’s a lot of red tape and capital required to get started. The quickest route to market was to sign up as an affiliate for an insurer. This meant I could launch quickly and gauge feedback, but it came with lots of downsides. I had little control over the design and technology, and I couldn’t build a relationship with customers because they technically weren’t mine. I was able to get 55 paying customers and a lot of positive feedback. That was enough for me to want to keep iterating on it.”
Ashley used networking, referrals, Twitter, and SEO to market the idea. The initial set of users were friends who further invited their friends. Leads from organic search were effective as there weren’t many bespoke insurance providers targeting freelancers at the time. With Jack is completely bootstrapped and the team comprises of freelancers. Quotes are still processed manually and this has enabled the company to have direct conversations with customers and understand their needs. However, a plan to automate the process without losing the personal touch is in the pipeline.
“ For me it’s important to acknowledge the experiences most people don’t talk about — the difficult parts. Sure, it’s fun to share the milestones of hitting 300 customers or selling £100,000+ of insurance, but to get to this point I had to spend 2 years looking for an insurer to partner with. 2 years of rejection and dead end meetings. None of that was fun and I came very close to giving up. I’m glad I didn’t. To stay motivated I think you have to serve an audience you like (for me that’s freelancers) and work on a problem that interests you (improving the insurance industry). If I was in this just to make money I’d have given up long ago. I’ve seen first-hand the scary situations freelancers face and how insurance can help them. I recognise and believe in the value of insurance and now I’m on a mission to get every freelancer insured.”
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