April's mini experiment

I want to get back to growing With Jack after a year of distraction by running lots of mini experiments and being more intentional with measuring results.

This month I focused on creating landing pages for specific industries (photographers, marketers etc) and improving existing ones.

Prior to April's mini experiment we had landing pages for:

  • graphic designers (one of our most popular pages on the website)
  • web designers
  • web developers

Instead of blindly picking random sectors, I looked through 2000+ customers to uncover who is using With Jack to arrange their insurance outside of the above. It's overwhelmingly:

  • photographers
  • marketers
  • copywriters

I started with photography because, as an ex-photographer, I know this space well. I have almost a decade of experience as a wedding supplier so I can speak first-hand of the worries photographers have.

Given photographers account for almost 25% of our claims, I have a ton of real examples to use when writing content. Cost of claims, most used policy features, average premium…

Using Ahrefs for content optimisation

Ahrefs ranks "insurance for photographers" as medium difficulty. The UK search volume is only 100/month.

I'm still figuring out how to use Ahrefs to inform what I write, but it did highlight that photographers are likelier to search for content around public liability insurance than any other product.

That's interesting. After 8+ years in business we've had claims for photographers across all of our products except from public liability. I have a feeling the popularity of this term is because some venues require it so I leaned into that. Come for the public liability content, stay for the contents insurance!

Once I published the photography landing page, I created some internal links from elsewhere on the website and gave it its own post on the grid.

Rank tracker tells me I've picked up several SERP features for photography-related search terms already, but we're not featured on the first page of Google yet.

As an aside on search intent, last week was the first time a customer informed me they'd found us through ChatGPT. I'd imagine fewer people will be relying on search engines to find recommendations as the popularity of AI tools grow.

The copywriting and marketing landing pages had no keyword difficulty or search volume in Ahrefs. These are two industries we overwhelmingly cater to so they're looking for us somewhere.

Using Reddit for content optimisation

Since I didn't have any related terms or search queries to assist with creating my landing page I turned to Reddit. There's a sub-reddit for everything. If I'm ever stuck for inspiration I'll head to a related sub-reddit and search for 'help', 'difficult client' or something along those lines.

Reddit never disappoints. I'd advise everyone creating content to lean into Reddit. If you don't have an existing audience to tap into, Reddit can help to inform topics, the language your audience use and common themes. It's a goldmine of information.

I also used Ahrefs to see what pages competitors are ranking for with the keywords I'm optimising for. Many insurers are still using "no admin fees" or "UK call centres" as a selling point instead of what the product can actually do for a freelancer.

I'm surprised they aren't exploring the Jobs To Be Done framework where you write copy from the perspective of the job your customer is hiring you to do. For example, it's likelier a freelancer will seek out advice about late payments as opposed to speak to a UK based rep. This is the best book I've read on JTBD.

Since optimising our existing landing pages and launching these new ones:

  1. we're on the first page for the 'insurance for web designers' keyword
  2. we're ranking for a new keyword, 'web developer insurance'. Currently at position 14 so I need to improve on that
  3. we're ranking for a new keyword, 'insurance for photographers'
  4. we're on the first page for the 'graphic designers insurance' keyword

Overall we're seeing a slow but steady increase in traffic to With Jack's website, which I believe is a culmination of the 4 experiments. No rocket-ship growth over here, but I've working been in insurance for 2 decades—I wouldn't expect anything different.

Despite the increase in traffic, April was a tough month.

The Easter holidays contributed to a slow month for enquiries (it feels like there's a holiday every month?). I always see a drop in sign-ups when it's the school holidays because freelancers are usually responsible for child care. However, in the last week of April we had a flurry of activity and lots of new sign-ups.

I also had a difficult month personally. It was my mum's birthday and what we went through at the start of the year is catching up with me. People told me it would take months to sink in, but having lost my dad at 18 I thought I was aware of what to expect. I've either misremembered grieving for my dad or I'm having a different experience this time around. Either way my concentration and productivity levels were very low this month.

Sometimes I feel guilty when I'm unproductive. Shouldn't I be working harder? Trying more things to grow the business? But my friend, Brittany, says now is the time to wrap myself in cotton wool. I am trying to be kinder to myself.

If April taught me one thing, it's to schedule less meetings and commit to less work obligations overall.

Looking back at the first quarter of mini experiments

If you're new here, here's a recap of my monthly experiments:

I can only see 1 new backlink from an existing customer this month. Given the flurry of new sign-ups we had towards the end of April I'm hoping more adopt the "insured by" badge.

For social media I've dropped my posting schedule to twice a week because I'm worried about continuing to come up with new content. If it massively affects engagement then I'll return to posting three times a week. So far there's been a small drop-off but followers are still growing.

The sponsored content has resulted in enquiries and backlinks. The DIFTK podcast in particular has been a great investment. Plenty of people are mentioning them when emailing or getting quotes, plus we get a spike in social media followers when they tag us. They've also been kind enough to share some of our content on their social media. I believe we have 2 episodes left, but I'd consider sponsoring more.

A look at May's mini experiment

We're already into the first week of May. Thanks to a bank holiday and taking a short break to Lochearnhead I hadn't given May's experiment much thought. I need to be more on the ball and start prepping for my mini experiments in the lead up to month end.

I'm competing in the Four Nations Championship next week and need to do a water cut and be in a deficit to make weight, so I need to keep this month light on the brain.

I'm going to focus on SEO, in particular drawing inspiration from this Reddit thread. I've contacted one of my customers to conduct a SEO audit for us, too.

We're ranking for keywords like "insurance for freelancers", but I'm hoping that long tail keywords where people are looking for solutions to their problems improve traffic and sign-ups.

Ashley Baxter

Glasgow, Scotland

I'm building With Jack where my goal is to help 10,000 freelancers. I also play video games, take photos and do strongman.