Portfolio project

Rebrand of With Jack — Insurance for UK Freelancers

With Jack offers business insurance for creative freelancers in the UK. Being more personal and different to other insurance companies, it’s probably the most likeable insurance company I’ve ever met.

With Jack came to me because the existing website did a good job of conveying the brand ethos — but it didn’t tell creatives why they should sign up.

In order to find the messaging that would help grow the brand, we embarked on an in-depth conversion copy project, consisting of Research & Discovery, Writing & Wireframing and Testing & Learning.

The new copy has been rolled into a wider rebrand and will go live in stages. We’re testing and learning from the results as part of our ongoing conversation.

Ashley, the company founder and director, has written a comprehensive behind-the-scenes of the rebrand, too. She says:

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. …

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.

Research & Discovery

With Jack’s branding was already strong.

But the value proposition, “Business insurance on a first-name basis”, only appealed to freelancers who were already looking to buy business insurance.

To find the right value proposition to attract all the other freelancers, I analysed customer feedback, (anonymised) customer emails and anecdotes from freelancers. Which job did freelancers hire business insurance to do for them? I looked at analytics to determine what was working, and Ashley and I spent time exploring where she wanted to take the company in future. She then mapped the customer journey together with the project’s UX designer. This map was an incredibly useful tool when designing the messaging.

With a solid background writing for insurance companies, I only needed to catch up on the latest developments to make sure my copy didn’t stray from the all important regulations.

Now that I knew exactly what we wanted to achieve, I analysed With Jack’s existing website, a competitor’s website and the site of a brand Ashley loved, comparing them in terms of User Experience, Content and Tone of Voice.

This allowed us to discuss different ways of handling important stages in the user journey and draw up a roadmap for optimising the copy.

Writing & Wireframing

Now it was time to develop the new brand messaging.

With Jack already had beautiful illustrations and a strong nautical theme, which we wanted to keep alive.

But the copy did not engage with the illustrations at all — they lived side by side.

One key consideration therefore had to be how the copy could relate to the nautical theme without distracting from the product (insurance), sounding too childish, or becoming to pirate-y.

My Copy Strategy Report addressed those key questions without me having to do lots of rewrites.

With Jack’s homepage had to be rewritten from scratch: it was going to take on a new job as the landing page for freelancers who weren’t sure if they wanted insurance.

Based on my earlier research, I was able to determine a messaging hierarchy that would speak to their reality and dreams, as well as giving them enough rational facts to make an informed decision.

One of the best features of With Jack’s website had always been the conversational quote system. I drew on years of scripting automated phone systems to tighten up the conversation, inject even more personality and make it behave more like a human.

Web developer Scott Riley was working to fully automate the backend. Getting a quote and taking out insurance was going to be much more fun!

Next, we optimised every single subpage to make sure the messaging was on point, related to Vic Bell’s illustrations and supported the ideal customer journey.

One area where my background in customer care could add special value was the new FAQ site, which we completely restructured.

The goal was to make the right info easy to find as well as easy to understand — removing as much ‘insurance lingo’ as possible.


The first stage of the new copy launched at With Jack’s quietest time: late October 2018. Already less than 6 months after go-live, there’s been good uplift:

* 5% increase in online conversions
* 15% increase in monthly premium that’s sold through the website
* Fewer customer queries

Because With Jack’s business is seasonal (winter is quiet and there’s a dip in summer, too) it’s interesting to compare performance at the same time in the previous year:

* 55% increase in turnover compared to same time in 2017
* 36% increase in new customers compared to same time in 2017

This is the most exciting part of any project: seeing the new copy live and observing how users interact with it. As we learn what works, we can improve the messaging further. If you’re curious, take a peek at With Jack’s website from time to time and see it evolve.

Are you looking to grow your brand?

If you’re not reaching all the people who’d benefit from your offer, new messaging can take you far.

It’s not always necessary to also change the visual design or website functionality. The copy in this project would have worked with minor tweaks to the existing page.

But then, sometimes new words inspire new pictures…

Has your brand outgrown its messaging?

Let’s have a chat about optimising your website copy.


Sabine Harnau

From Scratch Communications




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