Optimising a brand to reach new audiences

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.

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

I also reviewed (anonymised) customer emails and freelancers’ anecdotes.

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

Insurance is a heavily regulated industry, and so I was not going to be able to just “write what I want”.

I already had a solid background writing for other insurance companies, so I could focus on catching up on latest developments and due diligence.

Ashley told me 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.

Now that we 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.

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.

Before I got started on the actual copy, I collected all my recommendations in a Copy Strategy Report.

This way, Ashley and I could address the key questions without 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 were not sure if they wanted insurance.

Based on my 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.

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.

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.

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

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

One area where my background in customer care could add special value was the new FAQ page, which I 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 new layout makes it easier to scan for the right question. And the most important question – what to do if you need to make a claim – comes first. This represents a shift in thinking: From what the business wants to get across to a research-informed, customer-focused perspective on what will increase conversions and reduce churn.