Interview with Ashley Baxter, founder of ‘With Jack’

We’re thrilled to interview Ashley Baxter, founder of With Jack, a UK-based insurance provider dedicated to empowering freelance creatives.  

With a mission to simplify insurance and provide a personal touch, With Jack protects freelancers from the unpredictable waves of client disputes, unpaid invoices, and equipment mishaps.  

In this interview, Ashley shares her journey of building a business tailored to freelancers, the challenges and triumphs of niching down, and her vision for supporting the freelance community.  

From debunking insurance myths to revealing the sentimental story behind With Jack’s nautical branding, Ashley offers candid insights and practical advice for freelancers navigating their careers with confidence.  

Let’s dive in!

You’ve chosen to target a very specific niche in freelancers, why did you make that choice and what have been the pro’s and con’s? 

There were a few reasons I landed on targeting freelancers. One was that I had been freelancing on the side and had a poor experience buying insurance coupled with a scary situation with a client.  

Because providers weren’t niching down, I didn’t understand how the insurance I’d bought could help me.  

Then I had a scary situation with a client and being insured helped me navigate it. I had a much better outcome than had I been uninsured.  

The other reason was that when I launched a generic landing page for my initial version of what would become With Jack it was overwhelmingly freelancers that registered their interest. 
 
With Jack’s website emphasizes “one solid policy and the personal touch.” What does this mean to you, and how does it set With Jack apart from other insurance providers? 

Instead of multiple products with different start dates and direct debits, you customise one policy by bolting on the products you need.  

This can be customised at any point during the policy term, making it super flexible. With the personal touch, our whole service has been concierge since launching (a real human working with you at every point of the transaction.  

All manual processes but concierge sounds fancier!). We’re launching our automated system in September so we can free up our time to develop new products but being in the trenches with our customers will still be at the heart of the business, it might just look a little different. 
 
Have you found there are any common misconceptions freelancers have about insurance? 

Yes, I’ve been doing this for 9 years so common misconceptions I hear are “I have a contract so I don’t need insurance”.  

A contract doesn’t stop a claim from being brought against you. In fact, you can even be in breach of your own contract.  

Contracts outline the duties that are to be expected of both parties and insurance is what steps into action when those duties come into question.  

Another misconception is that insurance will only assist at the point solicitors are banging on your door.  

Legal action is one of the events that triggers policy coverage, but a good provider will offer more holistic support and value added services so you’re getting value on a more consistent basis. 
 
How do you gather feedback from your users, and how does it influence your service/product decisions? 

I use iteratehq.com for surveys, both pulse surveys and more general feedback embedded on the website.  

We do focus groups. I had a communications consultant conduct these with the upcoming launch because I had a lot of bias.  

Part of this launch initially included a lot of community and educational features, but from the focus groups it became clear this was a low priority for people so we’ve pressed pause on that. 

Things like freelancers aren’t really aware of their rights when it comes to chasing late payments so there’s a big information gap, and that there are factors that influence how they’d pursue late payments like their existing relationship, value of invoice etc.  

All of this has been helpful with developing the product. We have quite an engaged customer base so we try to tap into that. 
 
With Jack has a distinctive tone and visual identity. Can you provide some background to the brand building process, and what values guided it? 

My brief was to not sound or look insurance-y and to be more human.  

Although the branding and team has changed, that’s been the central theme as we’ve evolved. I named the company after my dad because he’s the reason I got into insurance.  

He’s the mascot, Jack, that you see throughout the site. The nautical theme was a happy accident.  

The design team suggested it because there are analogies around lighthouses guiding you and lifebuoys keeping you afloat in turbulent times, but what they didn’t realise was that my dad loved fishing and boats so for me the branding is very sentimental and adds to the human element. 
 
You’re very open about the running of your business on your personal blog, including successes and failures. Why have you chosen to do this? 

One of my favourite things to do is look back on my writing from when I launched With Jack. It takes me back to how I felt at that time and all of the small milestones I hit.  

It’s also a reminder of how far I’ve come because sometimes I can convince myself we’re not growing fast enough or I should be further ahead.  

Writing is powerful because I have a habit of misremembering or bending the truth, but by documenting what’s happening I can revisit and relive it.  

So it’s more for personal reasons but published publicly… even though hardly anybody reads my blog! (20i note: read it here) 
 
 
What’s been the most effective channel or tactic for reaching your audience? Any unexpected wins? 

For us it’s been podcast sponsorship. In our industry it helps to have someone talk about the product that isn’t a broker. 

Freelancers don’t relate to insurance brokers, but if another creative is talking about insurance and how it’s helped them they pay more attention.  

An unexpected win has been the short-form reels we’ve been publishing on Instagram. They seem to land well with existing customers.  

When we publish one we’ll get a string of support requests like “I saw your reel about working with US clients. Can you look at my policy to make sure I’m set up for that?”. 
 
If you could go back to day one, what’s one thing you’d do differently? 

I’d have spent a solid 6-12 months building an audience in the freelance space so that I had people to launch to from day one.  

I don’t think I’ve done myself any favours relying on platforms like Twitter to reach people. I wish I’d spent time building my audience and engaging with them in a medium like email before I started my business. 
 
How do you see the freelance economy evolving in the next 12 months or so? 

Honestly I am hoping the freelance economy grows in confidence because of services like ours so that they feel more confident standing up to difficult clients and putting more pressure on late paying clients.  

If we do this collectively it might be enough to have bad clients think twice about mistreating freelancers in the future.  

But I see that as a long term goal instead of something that will change over the next 12 months. 
 
What’s one goal you have for With Jack that you’re really excited about achieving? 

I want to build a product for late payments. Lots of freelancers aren’t aware of their rights when it comes to non payment.  

We launched a credit control service to test the water and have recovered over £40,000 of invoices. 

Now it’s about trying to productise that and it really excites me helping people get paid! 
 
What is the greatest video game of all time? 

I wish I could play the Bioshock franchise with fresh eyes all over again.