How to Optimise a Brand to Reach New Audiences — A Case Study

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 you’ll ever meet.

After a year of building With Jack, it was time to optimise the brand message.

Ashley, With Jack’s founder and director, came to Sabine 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 has written a comprehensive behind-the-scenes of the rebrand, too, which we highly recommend — especially if you’re in tech or growing a startup.

In it, she’s incredibly generous with her praise:

“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.”

— Ashley Baxter, founder & director of With Jack

Research & Discovery

With Jack’s branding was already strong.

The value proposition, “Business insurance on a first-name basis”, seemed utterly attractive.

But it was clear that this would only appeal to freelancers who were already looking to buy business insurance.

With this in mind I decided to start with research.

Analysing customer feedback to find the ‚job to be done‘

Ashley had already collected an impressive amount of useful customer feedback that we could analyse for common themes.

Sabine also reviewed (anonymised) customer emails and freelancers‘ anecdotes.

Which job did freelancers hire business insurance to do for them?

Researching compliance needs

Insurance is a heavily regulated industry, and so Sabine wasn’t going to be able to just „write what she wants“.

She already had a solid background writing for other insurers, so she could focus on catching up on latest developments and due diligence.

Understanding the brand — past, present and desired future

Ashley told us the backstory of With Jack and explained the marketing decisions she had made thus far.

We looked at analytics to determine what was working, and spent time exploring where she wanted to take the company in future.

Independently, Ashley mapped the ideal user journey for her optimised website. This map was an incredibly useful tool when designing the messaging.

Competitor mystery shopping report

Now that we knew exactly what we wanted to achieve, Sabine 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.

Captain's hat, one of the illustrations used in the old branding of With jack
An example of the excellent illustrations ‘humanising’ this insurtech brand before the rebrand.

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 preserve.

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.

Designing the Copy Strategy

Before Sabine got started on the actual copy, she wrote down all her recommendations in a Copy Strategy Report.

This way, Ashley and Sabine could address the key questions without having to do lots of rewrites.

An excerpt from the copy strategy report for with Jack

Be a confident freelancer: developing the new value proposition

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 her earlier research, Sabine 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.

The value proposition of With Jack as it appeared on the homepage before the 2018 rebrand: Business insurance on a first name basis.
The value proposition of With Jack as it appeared on the homepage before the 2018 rebrand.
The revamped hero section of With Jack’s homepage after the first stage of the 2018 rebrand had been rolled out: Be a confident freelancer.
The revamped hero section of With Jack’s homepage after the first stage of the 2018 rebrand had been rolled out.

Improving the narrative UX of the conversational quote interface

One of the best features of With Jack’s website had always been the conversational quote system.

To make it even better, Ashley’s 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.

Sabine 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.

For example, she removed any mention of „worry“ and made sure Jack always interacted on a first-name basis:

The quote system used by with jack before the 2018 rebrand
Getting a quote from Jack was already a super cool experience before the rebrand…
The quote system used by with Jack after the 2018 rebrand
… but now it’s even more human, and even easier to use.

Applying the new copy strategy to the rest of the website

Next, we optimised every single subpage to make sure the messaging was on point, supported the visual design, and supported the ideal customer journey.

One area where Sabine’s 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.

with Jack FAQs before the 2018 brand refresh
with Jack FAQs after the 2018 rebranding.

A new era for insurance With Jack

The first stage of the new copy has only just gone live, together with the brilliant new visual design created by Vic Bell and the slick new functionality created by Scott Riley.

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.

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