The Process And Reasons Behind With Jack's Rebrand

The Process And Reasons Behind With Jack's Rebrand

In 2016 I launched the first version of With Jack from a hotel room in Germany. I remember that moment well. My sister was with me and I quietly pushed it live before heading out to explore Berlin. I had no idea what lay ahead, but I was ready for the journey. This was a long time coming.

August 2016. Just after I'd launched With Jack I explored Berlin with a beer and some Haribo

Just recently, I launched the newest version of With Jack from a hotel room in Croatia. Note to self: stop launching stuff whilst travelling!

I was speaking at MicroConf in Dubrovnik and—after experiencing DNS issues over the weekend—the launch fell on the day of my talk.

The view from my head when I launched the new With Jack in Croatia. Not bad.

The difference between those two years is huge. Least of all that I have a business with hundreds of customers now and my hair is longer.

The biggest difference is the knowledge and experience I’ve gained over the past 2 years. I feel in a completely different place as a founder. I have a clearer understanding of what I’m building, where I’m taking it and what I’m trying to accomplish. This formed the basis of why I decided to rebrand With Jack.

Related: If you’re waiting until you’re ready or more experienced before starting a business, my advice is to just begin on a small scale. The best and quickest way to learn is on the job. Not from reading books or listening to podcasts about how others have done it. It’s just by doing it.

The 'Why?' Behind The Rebrand

When I first launched With Jack, there were some important things I didn’t yet fully understand;

  1. The exact role insurance would play in a freelancer’s life. I had an idea of its benefit and had spoken to a few freelancers who had used their insurance, but hadn’t seen it in action with my own eyes. Now With Jack has helped a number of freelancers with situations from being accused of IP infringement to replacing stolen equipment.
  2. The future of With Jack and what I wanted it to be. When I first launched my focus was on improving design and tech in the insurance sector, making it easier for freelancers to get insured. Whilst that still interests me, I now realise it’s not a pressing enough problem to have the 2,000,000 UK freelancers flocking to sign up to my business. With Jack is solving a different problem.

As a result of helping hundreds of freelancers arrange insurance, I’ve learned where the real value of this insurance lies. I’ve also formed a clearer understanding of what problem I want With Jack to solve (hint: we’re not a website that helps freelancers easily buy insurance. What you’ll see With Jack evolve into over time is a platform that helps to keep freelancers in business).

The old website did a good job of showcasing With Jack’s ethos (a personable, likeable and friendly insurance company), but it didn’t reflect the things I’d learned above. It failed to educate freelancers about how insurance can help them and didn’t do a good job of selling the product.

I think I’ve grown a lot as a founder. I also feel With Jack has grown up. It was time to reflect these changes with a new identity, website and onboarding.

Our aim with the rebrand was to:

  • do a better job of showing the value of insurance and explain how it can help freelancers
  • show With Jack is growing up and moving into a new stage of its life
  • illustrate Jack will be there for you, watching over you and ready to act when you need him

Getting To Know My Customers And Using That Research To Influence The Rebrand

Most of my competitors take funding, build the tech and launch with a complete solution. I did the opposite (not intentionally. I thought it was the only option available to me). But it turns out restraints have been good for With Jack.

With manual processes, I’ve been able to dip my toe in with minimal overheads and expenses and build my business to a profitable place. It also means I’ve had hundreds of customer conversations because I’ve been manually onboarding users.

This became the research that influenced the direction of the rebrand. From these customer conversations, I picked up on several things;

  • The language freelancers use when talking about insurance
  • The problem they feel With Jack solves for them
  • Why they were signing up and what they thought of the experience
  • Common confusions and questions about insurance

For example, I’d have customers tell me how they’re able to “sleep at night” and “interact with clients more confidently” now they’re insured. That language was important. This took us from the ‘Business Insurance on a First Name Basis’ tagline to the ‘Be a Confident Freelancer’ tagline.

Everything I’ve learned from these customer conversations has influenced the new direction. Not just the copy, design and illustrations but products and features I’ll be adding in the future.

It’s funny. Launching with manual processes was something I thought of as a hindrance 2 years ago. In hindsight it’s been the most useful way to learn about my customers, what they want and shape the direction With Jack is heading in.

With the next feature or product you build, my challenge to you is to ask yourself, “Can I do this manually instead of building tech to automate it?”. You’ll gather a lot of insightful data as a result.

There was a downside to manually onboarding customers, however. Having to process every quote myself was time consuming. I’m not sharing the workload with anyone else and sometimes I’d get to mid-afternoon and hadn’t done any work that would bring people to the website.

So, alongside the rebrand we launched a new quote system with instant pricing. People can now compare different cover options, tailoring their insurance to their budget and avoid waiting for a quote to be emailed to them. This will free my time up to focus on other work.

There’s a decision we made with the quote system that I want to mention. It’s these small decisions we made throughout the rebrand that (hopefully) show you what kind of business I want to build.

We made the decision to display the price upfront, before collecting your contact details. I don’t think anyone else in insurance does it this way (because the follow-up is important for hitting sales targets), but it’s a small way of showing that With Jack respects and puts you first.

A lot of us are jaded with the big, tech kings. There’s a shared feeling of mistrust when it comes to our personal information. They’re selling our data, they’re extracting more information from us than they need… I felt the right approach to take was, “We trust you to make a decision that’s right for you and if you think that’s With Jack, then we’ll take your contact details”.

It’s potentially a terrible business move as it’ll reduce my number of follow-ups. It hasn’t been long enough to see how this impacts the conversion rate and cash flow, but it feels like the right thing to do.

It’s been 2 weeks since launch and I’m happy with the amount of activity we’ve had.

The next step is to be able to bind policies from With Jack’s website, but I need a binder with the insurer to do that.

The Power of Good Copy And Tone of Voice

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. I met Sabine when she lived in the UK and used With Jack to arrange her insurance.

Sabine has done a wonderful write-up on creating the copy for With Jack, our process and what we tried to achieve. I’m not going to rehash it here, so please read Sabine’s case study.

What I will say is that 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.

Here are some things Sabine touches upon in the case study:

  • The original brand would only appeal to freelancers who were already looking to buy business insurance. That was something we needed to change. The new website would need to take on a new role of attracting freelancers who weren’t sure if they wanted insurance.
  • Sabine acknowledges that working on an insurance website meant she couldn’t just write what she wanted. Insurance is a regulated industry and there are certain words we can and can’t use to be compliant. Fun!
  • Illustrations have always been a big part of With Jack, but the original copy did not engage with the illustrations at all. Sabine had to consider how the copy could relate to the nautical theme without distracting from the product.

The New Look (Plus Things That Didn't Work Out Well)

There was nothing wrong with the ‘old’ Jack, but he had existed since May 2014. 4.5 years in internet years is… forever.

(If you’re confused about why the brand’s existed for 4.5 years when I officially launched in 2016, I started as an affiliate for an insurance broker in 2014. I might write about this another time.)

Along with shipping instant quotes, learning to communicate the value of insurance in a freelancer’s life plus some big news I’ll be sharing with you in a few weeks, it felt like the right time to illustrate the next stage of Jack’s life with a new look.

I can’t take any credit for the rebrand though. I felt pretty insignificant throughout the process. All credit goes to this amazing team of people;

I’m really happy with how everything turned out, but it wouldn’t be my style to only focus on the positives. I want to mention some things I wasn’t happy with or didn’t do right.

Treating It As One, Big Launch

Originally there was no rebrand. If I remember correctly (yes, it was so long ago this project started that I can’t remember), the aim was to roll out instant quotes and update the copy. That came before any notion of a full rebrand, but one thing lead to another…

I made a decision to launch the new quote system alongside the rebrand, instead of shipping smaller features on a more consistent basis. This delayed launch, hindered momentum and put me in a bad headspace. Coupled with a few other events in the business at the time, it felt like there was little progress being made and things were stagnating. I didn’t feel in a good place in July / August. I wonder if it would have been better to ship the redesign in various stages (copy, instant quotes, rebrand).

A Lot Of Work For Something That Never Materialised

We started redesigning the quote system because I thought I was getting a binder with the insurer (being able to bind polices from With Jack’s website), but that fell through.

This was the most frustrating part of the year because I had spent many hours working on my application—something I felt out of my depth with—only for it to not happen. It’s an awful feeling to work really hard on something only for it to never materialise. Especially when my time is already spread so thin being a solo founder.

We stripped our redesign back to just instant quotes, but that problem with the binder delayed the project and took us on a detour.

Hopefully it’s apparent how much thought and work went into this from everyone involved. I’d love for you to check out the new With Jack. Let me know what you think of it and please help us spread the word. With Jack grows solely on word of mouth, so telling others about it really helps.

And no more launches from hotel rooms in foreign countries with crappy WIFI.

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Navigating A Funk As A Solo Founder

Navigating A Funk As A Solo Founder

One of the most challenging aspects of building With Jack is staying motivated as a solo founder. When I recognise I’m having one of those days I give myself permission to write it off.

I’ll do the bare minimum at work, go home and play video games or hit the gym. I’ll do whatever I’m in the mood to do that takes me away from work—that’s the point.

I try not beating myself up about it, but sometimes those days extend to weeks and you’re in a prolonged ‘funk’. That’s where I’ve been recently and it hasn’t been fun.

The problem with being a solo founder is that there’s nobody to drag you out of that funk.

There’s nobody to pick up the slack so you can get the rest you need to recharge your batteries.

There’s nobody to give you a pep talk to motivate you.

It’s a scary (and potentially dangerous) place to be in. When I’m in this place my productivity levels only function at, like, 25%. A few days of not accomplishing much will have me sink deeper into that funk.

I’m passionate about helping freelancers. I’ve seen the value With Jack delivers and I love what we’re building. I feel positive about its future.

All of that drives me forward, but it doesn’t mean I’m motivated 100% of the time. With this funk lasting longer than usual I evaluated what triggered it so I can avoid feeling this way in the future.


I’m working with a team of freelancers, but they’re based remotely and aren’t building With Jack full-time. This means I’m predominantly working alone. I also live alone. This is a lot of time spent in my own company. That’s fine most of the time as I function well in my own company, but recently the isolation has got to me.


This is a big one! Momentum is so important to morale, but we’ve been slow to ship updates. Whilst the business is growing (in the past 9 weeks I’ve shipped £20,000+ of insurance products), the platform itself hasn’t evolved much.

We’ve been working on a rebrand and developing the instant quote system for what feels like forever. I’ve held off on launching the new quote system until the rebrand is complete, which has slowed things down.

In June I realised waiting to ship a bunch of features as part of a big launch was a mistake, and instead I should focus on shipping smaller features on a consistent basis. This helps with momentum. However, 3 months later it’s clear I failed to take my own advice.

'Killing It' Culture

Whilst this was going on, I was looking around and seeing everyone else “killing it”. Of course, this isn’t true. Everybody is facing problems or challenges in their business, but we’re only shown the good stuff on Twitter, Facebook etc.

That’s why I’m keen to share the side of business (specifically bootstrapping as a solo founder) that isn’t glamorous. It’s also why I’m eager to follow up tweets like this:

With this:

Slow Growth

All of this was exasperated by a slow couple of weeks with sales. I’ve been spoiled by good growth lately. Since March the figures have been growing consistently, but there’s a lurking fear that it’s a fluke.

Slow weeks are inevitable for every business, but my mind instantly shifts to “my luck has run out. Time to apply for jobs”. That mindset doesn’t help with dragging me out of my funk. In fact, it puts me in an even deeper, emotional rut.

So, how did I get out of this funk? It’s important to have this conversation as it’s something we all experience. Whilst the solution is different for everyone, identifying what triggers it is a good place to start. For me, I’d say isolation and lack of momentum have been the biggest problems.

Knowing this, I started applying to business programmes to solve both these issues. These programmes would enable me to;

  • meet new people who are in ‘my world’ (business, technology, design)
  • make lasting connections. A lot of the time I hide behind my computer in Glasgow
  • feel inspired and learn new things, both of which could help with motivation
  • push myself out of my comfort zone (one of the programmes involved pitching to hundreds of people on stage in Las Vegas)

Unfortunately, all of my applications were rejected.

Enter Epicurrence


Whilst applying to the above programmes, I got a Twitter DM asking if I’d like to speak at Epicurrence—a design retreat in Yosemite. The timing couldn’t have been more perfect. I had a feeling it would be exactly what I needed, so I said yes.

  1. Meet new people
  2. Experience a new setting away from my house and office
  3. Get involved in activities away from the screen
  4. Push myself out of my comfort zone
Nevada Fall at Yosemite National Park

During the day we’d go on adventures such as hiking, kayaking and mountain biking. Hiking the Mist Trail in Yosemite National Park is one of my top life experiences. As is mountain biking alone through Yosemite and coming face-to-face with a coyote.

As the sun set, we’d gather around a fire and have candid conversations about burnout, diversity and creativity. All egos were left at the door. This was about creatives connecting on a level beyond just work.

Being interviewed by Pablo at Epicurrence
Being interviewed by Pablo at Epicurrence. Photo by Edgar Chaparro

Epicurrence was a once in a life-time opportunity, so it won’t be around to solve my next funk. However, it has reminded me of the importance of being involved in a community of like-minded individuals. Sometimes just being around others is enough to inspire creativity. This makes a huge difference to your day when you’re a solo founder.

I’ve also been feeling more motivated and we’ve locked in a date for shipping the rebrand and quote system. Spoiler: With Jack will look very different 5 weeks from now.

This experience has given me more focus and helped me refine With Jack’s direction. Community will inform the next stages of With Jack, too. But first, let’s ship that rebrand!

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Why I Quit Wedding Photography

Why I Quit Wedding Photography

On Sunday 12th August I photographed my last wedding. Not of the season, but forever.

When I tell people this they seem surprised. “But you love photography and you’re good at taking photos!”. I still love photography. That hasn’t changed because I don’t want to do wedding photography any longer.

There were a few factors that influenced my decision to stop photographing weddings. Some positive, some negative.

The Positive

With Jack is growing! I used to sign up 10-12 customers a month. Now it takes about 10 days to hit that number.

I’ve had a few stressful instances of juggling mid-week weddings with insurance customers. I like to give my work 100% of my attention, commitment and focus. You can’t do that juggling two businesses. It’s also not fair on clients.

I’m retaining 87% of customers based on the first cycle of renewals. Thinking ahead to next year’s wedding season, I’d be going into my 3rd year of renewals plus signing up new customers.

Judging by current growth, I could be single-handedly managing 500+ customers by next year. Things would be trickier to juggle.

The Negative

I used to enjoy photographing weddings. I’ve witnessed lots of beautiful moments and I’ve felt grateful being able to capture them for couples. For the most part I’ve had a great time.

However, that enjoyment has gradually been replaced with anxiety. I’ve been lucky to have only had a couple of difficult clients, but over the years I’ve found myself getting more stressed about wedding photography.

There are many factors that contribute to a good wedding (from a photographer’s perspective):

  • Weather
  • Location
  • Lighting
  • Family dynamics
  • Chemistry between the couple
  • Weather (yes, I mean to mention this twice)
  • Schedule

The frustrating thing is we control none of them.

Client Expectations Are Changing

I’ve also noticed client expectations changing, which I assume is down to social media. With Pinterest you get a snapshot into picture-perfect weddings. Some people use this platform to plan their entire day.

That’s OK, but when your mood board is a beach wedding with a Spanish sunset and alfresco dining, yet you’re marrying on the rainy banks of Loch Lomond… well, you might be disappointed.

Photographers can’t take what’s in front of us and make it look like what you saw on Pinterest, yet some people expect us to. I found those expectations crippling.

With Instagram, there’s the pressure for perfection. It’s not just weddings that are guilty of this, but life can become a bit like a series of curated photo opportunities.

I think many of us have forgotten what a wedding is about. It means different things to different people, but traditionally it was a celebration of bringing two families together. Now the meaning seems to be buried under the dress, flowers, favours, the cake…

The Last Supplier Standing

Sometimes the day doesn’t live up to couples’ expectations. They’ve spent years planning this and pouring over details meticulously. Weddings also don’t come cheap. Because of this there’s a lot of pressure on the day for it to go to plan.

Because the photographer is often the last supplier to still be in contact with the couple post-wedding, I think frustrations can sometimes be taken out on the photographer.

I’ve only ever experienced this on a couple of occassions, but it was really unpleasant.


Then there was the fact that—for the past 7 years—I’ve given up many weekends during the summer to photograph weddings. I’ve missed key moments in my friend’s lives. Baby showers, hen do’s, birthday celebrations. I even missed my friend’s wedding. That sucked.

I’m excited about getting my weekends back. I’m going to fill them with being creative, taking photos just for fun and seeing friends! I’m already scheming a photo project and have signed up to some CreativeLive classes.

Those are the reasons I decided to stop photographing weddings.

  • With Jack is growing
  • Wedding photographers have no control over the factors that affect our job
  • The pressure of keeping up with client expectations is too much
  • After doing this for 7 years, I need a rest
  • It’s just really stressful
  • I want my weekends back!

I’ve worked with amazing couples and witnessed a lot of special moments. Thank you to my past clients that involved me in their day. I’m humbled to have been a part of it, but now feels like the right time to say good bye to that part of my life.

Wedding photography gave me the financial platform to build With Jack. I used the money I earned from weddings to fund the design and development costs. Now the business is growing, I’m able to reinvest the profits from With Jack back into it.

It’s time to dedicate 100% of myself to creating the best online platform that helps keep freelancers in business.

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What I Learned About Product, Growth And Strategy At Turing Fest

What I Learned About Product, Growth And Strategy At Turing Fest

Turing Fest returned to Edinburgh for another year. It’s a multi-track, two-day conference for the tech industry spanning 6 topics—product, engineering, strategy, growth, marketing and culture.

I could only attend the first day as I was in Newcastle for a friend’s wedding on day two. This meant I could choose any of the talks from day one’s three tracks—product, growth and strategy.

When I attend conferences, I want to come away with ideas, inspiration or knowledge I can apply to With Jack. Here’s what I learned.

Roan Lavery | Product | Driving Growth vs. Building Core Value

Roan Lavery

Roan spoke about FreeAgent’s three-step approach to perfect product harmony. This was my favourite talk of the day. It felt the most relevant to what I’m doing at With Jack and was also the most practical talk I attended.

Step One: Articulate Core Value

Roan shared the core value map that’s helped articulate FreeAgent’s vision (making businesses happier by putting them in control of their finances).

I’ve been learning about JTBD recently and exploring what that means for With Jack, so this was timely content. I’ve been shifting my mindset from “we’re an insurance business” to “what are our customers hiring us to do and how do we help them succeed?”.

The core value map helps you make sense of user needs, jobs to be done and features, which is all tied together by vision.

Step Two: Map User Journeys

The idea here is to engage users with your core value early and often. There are various stages to do this—initial onboarding, early usage, established use and even when customers churn.

Roan walked us through FreeAgent’s user journey and the decisions they made to drive growth by engaging users with their core value. Remember, FreeAgent’s core value is to make businesses happier and more successful by putting them in control of their finances.

There were a few points in FreeAgent’s onboarding that frustrated users. By combining or removing steps they were able to improve the customer journey and user happiness. This puts the user closer to being in control of their finances quicker.

Step Three: Create A Balanced Scorecard

Roan introduced us to Google’s HEART framework.


I had never heard of this framework before, but it’s used to measure the quality of user experience. From there you can identify which areas need improved, helping you decide what to prioritise.

I recommend checking out Roan’s slides from his talk Driving Growth vs. Building Core Value.

Gabrielle Bufrem | Product | Bootstrapping User Research: No Budget, No Team, No Buy-in, No Problem

The reason I chose Gabrielle’s talk was because I’m bootstrapping With Jack and user research is a huge part of what I do. I think I’ve got a good handle on conducting user research without a budget, but thought I might pick up a tip or two from Gabrielle.

At the moment I schedule calls with customers and use Iterate to capture feedback from sign-ups and lapsed users. I’ll also meet them in person, if possible.

Some of the talk wasn’t relevant to me, such as how to get your team to buy into user research, because I work alone.

This talk was a welcome reminder to get out from behind your computer screen and speak to real people. That you should be recruiting your customers to be your user research.

With Jack has an engaged customer-base and they’re willing to share feedback, but Gabrielle provided some ideas for getting people to do your user research without a budget. She suggests giving away swag or early access to a beta.

See Gabrielle’s slides from her talk Bootstrapping User Research.

Steli Efti | Growth | The 7 Deadly Startup Sales Sins

Steli Efti

I’m familiar with Steli because of his podcast with Hiten Shah (I was surprised so few people had heard of him). This talk had a lot of swearing. Whilst I’m not offended by swearing, I felt the content of the talk was lost amongst that.

A few of my favourite sales takeaways:

  • Simply ask, “What will it take to make you a customer?”. This is very simple advice yet something I’ve never done! I dance around sales and feel uncomfortable being so direct. I’m going to try this next time someone’s on the fence or weighing us up against a competitor
  • Be confident in your product and don’t offer discounts. Discounting is a race to the bottom. Nobody expects to use their insurance, so it’s no surprise many don’t see the value in it and haggle on price. I rarely give discounts (my profit margin is small enough and I actually want to be in business for many years) and prefer to sell With Jack on having a great product and customer experience. This is something I feel strongly about. I don’t want to be known as the cheapest, I want to be known as the best
  • Follow up more often. Do it until you get a yes or a no. My current approach to following up is lax. I only follow-up twice because I hate the harassing sales culture of insurance. However, a large portion of my sales come from follow-ups so I know it’s effective. It’s difficult balancing respecting people’s time with driving growth

See Steli’s slides from his talk The 7 Deadly Startup Sales Sins.

Des Traynor | What We’ve Learned From Scaling to 0-25k+ Paying Customers

Des Traynor

Des was the keynote speaker and the talk I was anticipating the most. I’ve followed Des on Twitter for several months and enjoy his writing.

This talk didn’t disappoint, but it was typical I had a flurry of sales come through just before it started. This meant I missed the first 5 minutes, then spent much of the rest of Des’ talk processing and sending quotes.

I’m used to this. I’m not complaining. With Jack is growing—what more can I want? But I would love another chance to hear Des speaking and give it 100% of my attention.

The parts of the talk I did catch:

  • Questions to ask yourself before starting a business. Will this problem exist in 10 years? How do people currently solve it?
  • Knowing your competitors. There are direct competitors doing the same job as you in the same way. Secondary competitors doing the same job in a different way and indirect competitors doing a different job with a conflicting outcome (think Weight Watchers and McDonalds). Know your competitors and understand why people should switch to you
  • Understanding how people buy your product. Is it problem based where they’ll search for a description of their problem? (“My client is threatening legal action against me.”) Category based where they’ll search for a solution? (“I need insurance that protects my business”) Competitor based where they’ll search for a better version of what they have? Or brand based where they’re looking for you?

What I Liked And Didn't Like About Turing Fest

Mark Logan

I’ve fallen away from the conference circuit in recent years. It’s because of exactly what happened during Des’ talk—I was preoccupied with running my business. However, it’s not often something like Turing Fest happens on my doorstep.

One thing I felt let down by was that many of the talks weren’t as advertised. The content of them didn’t match my expectations from the titles. I attended many talks only to find the content was different to what I was anticipating. After speaking to others about this I know I wasn’t the only person who felt this way.

What I did like about Turing Fest is the variety of talks. Having 3 to choose from ensures you’re picking what’s most relevant to you at that stage in your business. I also like the shorter format of talks. They’re about half an hour long, which I think is the perfect length for a full-day conference.

I definitely picked up a few tips and ideas for With Jack. Now to get to work implementing them!

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Positioning Your Product To A Tiny Audience

Positioning Your Product To A Tiny Audience

There is no silver bullet in building a remarkable product and it might take you months or even years to find the right recipe, but if you start with a small audience and gather feedback on the way, your chance of coming up with a remarkable product or service will get much, much higher. — How Seth Godin Would Launch a New Business

My business, With Jack, isn’t reinventing the wheel. It’s all manual processes and I’m not doing anything innovative.

If you were to ask what makes With Jack different, currently I’d say not much. Sure, people enjoy the conversational interface instead of a generic form. And yes, customers are delighted when I respond to enquiries at lightning speed. But I’m not disrupting an industry.

What I am doing is building my book of customers. I’m talking to people and making discoveries that will in time lead to creating a remarkable product, all whilst growing monthly revenue.

This approach has enabled me to get to market quickly, at a low cost and start collecting insights.

Build a remarkable product for a tiny audience

I’ve created With Jack for a small audience. 70% of my customers are freelance web designers and developers. The rest is comprised of internet marketers, photographers and businesses that fall on the fringes of digital and creative.

If you’re a plumber or estate agent, I’ll recommend you go elsewhere.

Getting a quote with Jack means not being shown 200+ occupations that aren’t relevant to you. You won’t have to scroll forever to find a category you think you fit into.

We know who we’re building With Jack for, so every design, copy and product decision is influenced by that.

Positioning With Jack for freelancers means only showing the type of insurance that’s relevant to them. A lot of sole traders approach me with insurance packages they’ve purchased elsewhere that have uneccesary cover added.

It’s not that the insurer intentionally tried extracting more money from the sale. It’s that they’re targeting so many types of businesses, their customer journey, packages and products aren’t right for everyone. This means some businesses end up paying for cover they don’t need.

On With Jack’s blog, you’ll find stories that resonate with freelancers. You won’t read about the importance of public liability because of the risks working on a construction site presents.

Instead you’ll hear stories about insurance helping with scope creep, missing project deadlines and client relationships breaking down. You know, the kind of stuff that’s relevant to our target audience.

Lastly, once you’ve bought your policy you’ll receive a host of benefits that are relevant to the work you do. This includes discounts for software, eBooks or learning material for freelancers.

Perhaps I’ve overused the term ‘relevant’, but that’s the key word here. Applicable. Apt. Fitting. Because we’re not trying to target every type of business in all industries, we can perfect each area of With Jack for our tiny audience. That’s the power of positioning.

Why freelancers?

There were a few reasons I positioned With Jack for freelancers.

I had experience in their world

I was a freelance wedding photographer for 6 years. I know some of the fears I faced when freelancing. Equipment failing, not meeting client expectations. Maybe I’d miss a crucial moment at a wedding or work with a problem client.

There was one difficult customer I had (I was lucky for the majority of my freelance career). It was the first time I worried a situation could escalate to something more. Whilst it was a stressful situation to handle, there was a lot of comfort in knowing that I had insurance if it did escalate.

There would be a team of legal experts to help me and a policy to cover my defence costs. Even though the situation diffused after some time, that one difficult client—and the fear and anxiety I felt whenever I received communication from them—was worth the £300 I had paid for insurance that year.

I had a small audience to launch to

I had previously launched Insurance by Jack (I’ll talk more about this later). Whilst this project wasn’t a success, hundreds of people had submitted quotes which gave me a lot of data to analyse.

I surveyed every quote and noticed an overwhelming amount were from freelancers. This was clearly something they were interested in. It also gave me a small audience to launch With Jack to.

Most insurers target every type of business

There weren’t a lot of options on the market for freelancers. The incumbents that have a monopoly on business insurance target sole traders, limited companies, traditional tradesmen, digital trades, high-risk careers like financial advisors etc.

It felt like there was a gap in the market for somebody to say, “We do this one thing really well for this one group of people”.

I like freelancers!

Having previously worked in buy-to-let insurance and selling to landlords, I realised it was important for me to like the audience I’m serving. I measure this by asking myself;

  • Would I have coffee with them every day?
  • Do I enjoy chatting to them?
  • Am I interested in what they’re working on?

If I can answer ‘yes’ to those questions it’s the right fit for me as a founder. Justin Jackson has a great article on founder / market fit.

The importance of positioning

We’ve established that With Jack isn’t doing anything innovative. What it does a good job of is positioning. This means freelancers feel With Jack is unique to them.

Take these tweets as an example.

Only offered in UK currently but this is the kind of insurance I want for freelance work in the US.
Got super excited about this until I saw the .uk extension.
We need a service like this in the US—freelancer insurance.

With Jack specialises in professional indemnity insurance. This product does exist in the US and elsewhere in the world. It has existed for a very long time.

What’s confusing people is the terrible job insurers do of positioning. Remember, most insurers are trying to be everything to every type of business. They cater to large businesses with employees and complex risks the same way they’re catering to sole traders turning over less than £50K per year.

People are unaware this policy exists in their line of work because insurers take a product (in this case professional indemnity) and package it for lawyers, SME’s, freelancers and more.

These are all different sizes of businesses across different industries with different needs and risks. This leaves the messaging of how this product can help you lost, unfocused and—you guessed it–not relevant.

This is why positioning is important. Not just in insurance, but any business. It helps you speak directly to a particular group of people.

If With Jack was targeting plumbers as well as web developers, our messaging would be muddled. We’d be sharing stories about burst pipes as well as the dangers of scope screep. There’s no crossover and—as a result—our messaging wouldn’t ‘speak’ to anyone.

Web developers would visit the website and think, “I’m not doing manual labour. This product must not be for me”. Tradesmen would visit the website and think, “I’m not building features for a client’s app. This product isn’t for me”.

The result? Fewer sign-ups.

In the latest episode of Build Your SaaS, Justin and Jon are exploring what to charge for their podcast hosting app. They’ve been looking at how competitors price themselves and their differentiator.

Rob Walling, co-founder of Drip, offered advice on charging more than your competitors. First, you can have features that no one else has. Secondly, you can position yourself differently by saying: “We are the podcast host for businesses”.

Justin acknowledges the successful job ConvertKit did of positioning themselves.

Your positioning matters a lot. Is there a huge difference between Nathan Barry's ConvertKit, which is email marketing for bloggers, and MailChimp, which is email marketing for whatever. Is there a big differentiator? No. A lot of it is the language they're speaking.

ConvertKit is now doing $1,000,000 MRR. They carved a niche as email marketing for professional bloggers, and have evolved their positioning to email marketing for creators.

At With Jack, being clear on our positioning allows us to build a customer experience that’s easy to navigate, use content to deliver a focused message and offer the neccessary products to our target audience.

Positioning is scary. Trust me, I get it

Before With Jack there was Insurance by Jack. When I launched Insurance by Jack, I was trying to target lots of different businesses. Creative agencies, technology start-ups, freelancers and more. I was terrified of excluding people and losing sales. There was nowhere on the site that actually said who Insurance by Jack was for.

It’s no coincidence that Insurance by Jack never gained traction.

Lesson: Start by focusing on the tiniest audience possible. It doesn’t mean you’re stuck serving that tiny audience forever. Mark Zuckerberg launched Facebook for Harvard students and it’s now at 2.19 billion monthly active users.

It’s easy to think that by launching to more verticals you’ll increase sales. You might attract more people through the door, but it’s tricker to win them over.

A freelance web designer should feel like With Jack has been built for them. They should feel like we understand the challenges they experience as a designer, and have stripped out all of the crap so they can get the insurance they actually need, quicker.

Philip Morgan, a consultant who specialises in positioning, says that when you define your positioning you are making a claim of expertise. So, what do you want to be an expert in?

Our statement is that we understand freelancers and the kind of problems they face with clients. Because of this we can offer them a product (professional indemnity insurance) to solve those problems.

Other insurance companies insure 300+ industries and sectors. But being the insurer for all businesses means people don’t know what products to buy, if they’re applicable to them and how they serve them in their line of work.

Again, this isn’t exclusive to insurance. All businesses should be positioning themselves to occupy a niche.

Final thoughts

Positioning focuses your messaging, marketing, customer service and products. With Jack isn’t doing anything innovative (yet!), but we’ve done a good job of the above which is how I’ve been able to organically bootstrap to almost 300 customers.

It can be scary because you’re worried about excluding potential customers, but by positioning yourself to a tiny audience you’ll know things about your customers’ needs and problems that competitors don’t. This will give you an advantage. From there you can gain access to other ideal customers.

Positioning doesn’t mean you’re locked into serving that audience forever, but it’s a great place to get started. You’ll gather feedback and learn from your customers, helping you build a truly great product.

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