In 2016 I launched the first version of With Jack from a hotel room in Germany. I remember that moment well. My sister was with me and I quietly pushed it live before heading out to explore Berlin. I had no idea what lay ahead, but I was ready for the journey. This was a long time coming.

Just recently, I launched the newest version of With Jack from a hotel room in Croatia. Note to self: stop launching stuff whilst travelling!

I was speaking at MicroConf in Dubrovnik and—after experiencing DNS issues over the weekend—the launch fell on the day of my talk.

The difference between those two years is huge. Least of all that I have a business with hundreds of customers now and my hair is longer.

The biggest difference is the knowledge and experience I’ve gained over the past 2 years. I feel in a completely different place as a founder. I have a clearer understanding of what I’m building, where I’m taking it and what I’m trying to accomplish. This formed the basis of why I decided to rebrand With Jack.

Related: If you’re waiting until you’re ready or more experienced before starting a business, my advice is to just begin on a small scale. The best and quickest way to learn is on the job. Not from reading books or listening to podcasts about how others have done it. It’s just by doing it.

The 'Why?' Behind The Rebrand

When I first launched With Jack, there were some important things I didn’t yet fully understand;

1. The exact role insurance would play in a freelancer’s life. I had an idea of its benefit and had spoken to a few freelancers who had used their insurance, but hadn’t seen it in action with my own eyes. Now With Jack has helped a number of freelancers with situations from being accused of IP infringement to replacing stolen equipment.
2. The future of With Jack and what I wanted it to be. When I first launched my focus was on improving design and tech in the insurance sector, making it easier for freelancers to get insured. Whilst that still interests me, I now realise it’s not a pressing enough problem to have the 2,000,000 UK freelancers flocking to sign up to my business. With Jack is solving a different problem.

As a result of helping hundreds of freelancers arrange insurance, I’ve learned where the real value of this insurance lies. I’ve also formed a clearer understanding of what problem I want With Jack to solve (hint: we’re not a website that helps freelancers easily buy insurance. What you’ll see With Jack evolve into over time is a platform that helps to keep freelancers in business).

The old website did a good job of showcasing With Jack’s ethos (a personable, likeable and friendly insurance company), but it didn’t reflect the things I’d learned above. It failed to educate freelancers about how insurance can help them and didn’t do a good job of selling the product.

I think I’ve grown a lot as a founder. I also feel With Jack has grown up. It was time to reflect these changes with a new identity, website and onboarding.

Our aim with the rebrand was to:

• do a better job of showing the value of insurance and explain how it can help freelancers
• show With Jack is growing up and moving into a new stage of its life
• illustrate Jack will be there for you, watching over you and ready to act when you need him

Getting To Know My Customers And Using That Research To Influence The Rebrand

Most of my competitors take funding, build the tech and launch with a complete solution. I did the opposite (not intentionally. I thought it was the only option available to me). But it turns out restraints have been good for With Jack.

With manual processes, I’ve been able to dip my toe in with minimal overheads and expenses and build my business to a profitable place. It also means I’ve had hundreds of customer conversations because I’ve been manually onboarding users.

This became the research that influenced the direction of the rebrand. From these customer conversations, I picked up on several things;

• The language freelancers use when talking about insurance
• The problem they feel With Jack solves for them
• Why they were signing up and what they thought of the experience
• Common confusions and questions about insurance

For example, I’d have customers tell me how they’re able to “sleep at night” and “interact with clients more confidently” now they’re insured. That language was important. This took us from the ‘Business Insurance on a First Name Basis’ tagline to the ‘Be a Confident Freelancer’ tagline.

Everything I’ve learned from these customer conversations has influenced the new direction. Not just the copy, design and illustrations but products and features I’ll be adding in the future.

It’s funny. Launching with manual processes was something I thought of as a hindrance 2 years ago. In hindsight it’s been the most useful way to learn about my customers, what they want and shape the direction With Jack is heading in.

With the next feature or product you build, my challenge to you is to ask yourself, “Can I do this manually instead of building tech to automate it?”. You’ll gather a lot of insightful data as a result.

There was a downside to manually onboarding customers, however. Having to process every quote myself was time consuming. I’m not sharing the workload with anyone else and sometimes I’d get to mid-afternoon and hadn’t done any work that would bring people to the website.

So, alongside the rebrand we launched a new quote system with instant pricing. People can now compare different cover options, tailoring their insurance to their budget and avoid waiting for a quote to be emailed to them. This will free my time up to focus on other work.

There’s a decision we made with the quote system that I want to mention. It’s these small decisions we made throughout the rebrand that (hopefully) show you what kind of business I want to build.

We made the decision to display the price upfront, before collecting your contact details. I don’t think anyone else in insurance does it this way (because the follow-up is important for hitting sales targets), but it’s a small way of showing that With Jack respects and puts you first.

A lot of us are jaded with the big, tech kings. There’s a shared feeling of mistrust when it comes to our personal information. They’re selling our data, they’re extracting more information from us than they need… I felt the right approach to take was, “We trust you to make a decision that’s right for you and if you think that’s With Jack, then we’ll take your contact details”.

It’s potentially a terrible business move as it’ll reduce my number of follow-ups. It hasn’t been long enough to see how this impacts the conversion rate and cash flow, but it feels like the right thing to do.

It’s been 2 weeks since launch and I’m happy with the amount of activity we’ve had.

The next step is to be able to bind policies from With Jack’s website, but I need a binder with the insurer to do that.

The Power of Good Copy And Tone of Voice

A lot of people overlook the importance of copy when building a website. They focus more on how it looks and performs.

If done right, copy can be incredibly powerful in selling your product, mission or company. The copy was actually the part of the redesign process we started with. This was the work of Sabine from From Scratch. I met Sabine when she lived in the UK and used With Jack to arrange her insurance.

Sabine has done a wonderful write-up on creating the copy for With Jack, our process and what we tried to achieve. I’m not going to rehash it here, so please read Sabine’s case study.

What I will say is that working with a good copywriter made a huge difference to the project and I’d recommend it to everyone. Let the design come together around the copy.

Here are some things Sabine touches upon in the case study:

• The original brand would only appeal to freelancers who were already looking to buy business insurance. That was something we needed to change. The new website would need to take on a new role of attracting freelancers who weren’t sure if they wanted insurance.
• Sabine acknowledges that working on an insurance website meant she couldn’t just write what she wanted. Insurance is a regulated industry and there are certain words we can and can’t use to be compliant. Fun!
• Illustrations have always been a big part of With Jack, but the original copy did not engage with the illustrations at all. Sabine had to consider how the copy could relate to the nautical theme without distracting from the product.

The New Look (Plus Things That Didn't Work Out Well)

There was nothing wrong with the ‘old’ Jack, but he had existed since May 2014. 4.5 years in internet years is… forever.

(If you’re confused about why the brand’s existed for 4.5 years when I officially launched in 2016, I started as an affiliate for an insurance broker in 2014. I might write about this another time.)

Along with shipping instant quotes, learning to communicate the value of insurance in a freelancer’s life plus some big news I’ll be sharing with you in a few weeks, it felt like the right time to illustrate the next stage of Jack’s life with a new look.

I can’t take any credit for the rebrand though. I felt pretty insignificant throughout the process. All credit goes to this amazing team of people;

• Sabine Harnau for copy
• Vic Bell for illustrations
• Scott Riley for design and development

I’m really happy with how everything turned out, but it wouldn’t be my style to only focus on the positives. I want to mention some things I wasn’t happy with or didn’t do right.

Treating It As One, Big Launch

Originally there was no rebrand. If I remember correctly (yes, it was so long ago this project started that I can’t remember), the aim was to roll out instant quotes and update the copy. That came before any notion of a full rebrand, but one thing lead to another…

I made a decision to launch the new quote system alongside the rebrand, instead of shipping smaller features on a more consistent basis. This delayed launch, hindered momentum and put me in a bad headspace. Coupled with a few other events in the business at the time, it felt like there was little progress being made and things were stagnating. I didn’t feel in a good place in July / August. I wonder if it would have been better to ship the redesign in various stages (copy, instant quotes, rebrand).

A Lot Of Work For Something That Never Materialised

We started redesigning the quote system because I thought I was getting a binder with the insurer (being able to bind polices from With Jack’s website), but that fell through.

This was the most frustrating part of the year because I had spent many hours working on my application—something I felt out of my depth with—only for it to not happen. It’s an awful feeling to work really hard on something only for it to never materialise. Especially when my time is already spread so thin being a solo founder.

We stripped our redesign back to just instant quotes, but that problem with the binder delayed the project and took us on a detour.

Hopefully it’s apparent how much thought and work went into this from everyone involved. I’d love for you to check out the new With Jack. Let me know what you think of it and please help us spread the word. With Jack grows solely on word of mouth, so telling others about it really helps.

And no more launches from hotel rooms in foreign countries with crappy WIFI.