Last week I launched my insurance company, With Jack. I’d been in closed beta for 3 weeks prior, sourcing feedback from people who’d volunteered to test the onboarding process (thanks, people!).

Launch Week Analysis

I’ve shipped enough products to know that launch day rarely lives up to expectations. In the past I’ve romanticised launching, overestimating interest in my product and inflating figures.

A few underwhelming experiences have taught me to expect very little. A launch is generally one, big gamble.

Note: Insurance is a challenging asset to sell. You can only catch people once a year when their renewal is due. It isn’t a spontaneous purchase, so I wasn’t expecting a flurry of sales. Despite that constraint, I’m happy with how With Jack’s launch has went.

Fail To Plan, Plan To Fail

My tactic for past launches: throw a tweet out into the ether, hope somebody sees it. But this isn’t a side project—this is my business and I needed to have a plan.

For each day of the week, I gave myself a channel to focus on. Email, social media, blogging etc.


Bank holiday. Write off.

As I work for myself I’m oblivious to bank holidays. I had planned to launch on Monday, but found out the day before it would be a bank holiday in England and Northern Ireland.

I did send a few emails, but it was useless. Nobody was sitting at their computer on Monday.

Great start.


Tuesday was all about email.

Before I launched With Jack, I put up a landing page and wrote a couple of paragraphs on my vision for insurance, which I followed with a call to action to be notified of launch.

120+ people opted in. This is a good number for an insurance product. Having 10 people pay attention would have been a success.

Alongside With Jack’s existing newsletter of 60-odd people, I sent a launch announcement to this list. Only 51 people trickled through to the site.

Despite a poor performance, it’s true what they say about email being a captured audience. People who came from my list spent the longest time on the site. They visited the most pages, and the conversion rate for getting a quote was significantly higher than other channels!

I also emailed every beta tester to say thank you and notified them we had now launched. A few of them tweeted to their followers, which had a snowball effect of their followers tweeting about With Jack.

You may be thinking, “This doesn’t sound like you launched with much of a bang”. You’re right. I purposefully staggered my launch over the week. Why?

At this point in With Jack’s life, I have to manually process every quote that comes through. It’s time consuming.

I want people’s first interaction with Jack to be a positive one. They can get an instant quote elsewhere—I don’t want them waiting hours for mine. It was important not to overburden myself with work.

Day One:

  • 435 visitors
  • 14 (genuine) quotes


Next I turned to social media.

Twitter has lost its influence. Remember the days you could piggyback off Twitter to launch a business? Now the engagement rate is insufferably low.

But that’s where my audience is. Alongside a launch tweet, I experimented with two Twitter Ads on a budget of £20. In retrospect I should have experimented with more ads, but assign each ad a smaller budget.

My Twitter ad experiment
The Twitter ads I ran
“Bye bye, boring insurance forms. Hello, freelancer friendly insurance.”― TWITTER AD 1
“Insurance for freelancers serious about building a bulletproof business.”― TWITTER AD 2

I’m no copywriter, I think that much is obvious. When it was clear the second ad wasn’t getting much traction, I dropped it.

The first ad had 62 clickthroughs and gained With Jack 2 followers—1 of which got a quote.

Why did the second ad perform poorly? My guess is that the visual lacked impact. Showing a teaser of the conversational quote form on the first ad seemed to work well. The copy “Insurance for…” isn’t very engaging, either.

I also tried Facebook and Instagram ads.

My Instagram ad experiment
The Instagram ad I ran

The reach from Facebook and Instagram was a little wider (5380 impressions) and had more clickthroughs (131). The conversion rate for getting a quote was higher on Twitter, though.

Tristan from Ignite gave me some advice for running social media campaigns. He advised creating a lot of different ads, but boosting them for as little as £1 or £2 to gauge what works. I’ll be trying this tactic going forward.

Social media has been kind to us. A lot of wonderful humans have spread the word about With Jack, but it definitely doesn’t have the impact it once did.

(Note: Even though I set these ads to run on Wednesday, Facebook took 24 hours to approve them. This is why the traffic numbers don’t add up.)

Day Two:

  • 167 visitors
  • 7 (genuine) quotes


Thursday’s approach wasn’t about yielding instant results. I created a press pack and reached out to 10 publications I’d love to feature With Jack.

This was the first time I’ve done this. Writing a Twitter bio is hard enough, but a press release is a whole other level of self-promotion. Maybe I’d have benefited from reading Ryan Holiday’s book on PR.

I’m not sure how successful this will be. Due to a lack of responses from the people I contacted, I have a feeling there’s a skill to it that I haven’t mastered and this was a waste of my time.

Mark, who works in my office, has built a list of online locations to help give your startup “the launch it deserves”. He was kind enough to give me early access. I made my way through this list and submitted With Jack to relevant sources.

Despite Thursday not being about instant results, I doubled my traffic from day one. That was down to being featured on Designer News.

Day Three:

  • 949 visitors
  • 10 (genuine) quotes


Friday didn’t go to plan. I intended to drive traffic by writing a blog post.

There’s a lack of information about insurance for freelancers. I have a lot of ideas for content that will help to make sense of insurance, but do so in freelance speak—not insurance jargon.

Personal responsibilities got in the way, though, and I didn’t arrive at the office until after 1PM. I then had quotes to process and follow-up on, which kept me busy for several hours.

Fortunately, I was still riding on the coattails of the Designer News feature.

Day Four:

  • 1028 visitors
  • 13 (genuine) quotes

What Worked Well?

Being laser-focused on a niche. Insurance for plumbers? Yeah, I can do that, but you should know the benefits of targeting a niche by now. That’s why With Jack focuses on freelance designers and developers.

Because of this, word spread quickly and consistently through the freelance world. Knowing exactly who my audience was, I knew where to post about With Jack and who to reach out to.

Would it have had the same impact if I was also pursuing estate agents and tradesmen? No, I don’t have a clue about estate agents or tradesmen. By targeting everybody, you’re really targeting nobody.

I’ll leave generalisation to the big insurers. They have the marketing budget to get in front of everybody.

What Didn’t Work Well?

I dropped the ball in my personal life.

I lived on instant noodles for 5 days, not making the time to prepare my (usually healthy but time-consuming) meals. I’m suffering now. I’m bloated, lethargic and have a cold coming on.

My social life was impacted, too. I let people down last week. I hadn’t anticipated how busy I’d be or how tired a day of staring at a screen and processing quotes would leave me. I had an angry voicemail from my Gran for not visiting her.

Sell, Sell, Sell

As I said, insurance is a tricky thing to sell in that it’s purchased once a year. The stars have to align in terms of timing. Unless you’re a freelancer who isn’t insured and has never thought about it before.

With that said, I think launch week was a solid start. Some of these quotes will evolve into customers in the coming days, weeks and months.


  • 2579 visitors
  • 44 (genuine) quotes
  • 7 sales

Channels with highest conversions:

  • Direct (what does this even mean, Google Analytics?)
  • Designer News
  • Twitter
  • Email

The Emotional Impact

Unleashing your idea into the world is intense. I felt a number of things. Excitement, fear, elation, deliriousness

What if people hate With Jack? What if it’s a success and my life changes? Am I ready for whatever this throws at me?

It’s taken me a long time to get to this point. My journey began in 2005 when I inherited my Dad’s insurance business. Although things are getting better, I noticed insurers weren’t investing adequate resources into their design and technology. As a result, I wanted to build an insurance company with design and technology at the heart of it. It took years to get the ball rolling with this. I experienced lot of rejection and setbacks. Irrespective of how With Jack pans out, it’s a triumph in itself to even get to this point.

Despite the lengthy build-up towards launch—not to mention the intensity of launch week itself—the reality is the hard work begins now.

I’m blogging about how I’m building my insurance business and sharing everything on my newsletter.