Improving With Jack's Sign-Up Rate By 14%

Improving With Jack's Sign-Up Rate By 14%

This post is available in audio format.

I first mentioned With Jack’s conversion rate when writing about my goals for 2017. As of December 2016, 26% of people who got a quote with Jack became customers.

Over the past 12 months we’ve been tweaking key parts of the customer journey. The conversion rate is now at 40%—a 14% improvement from 2016.

Scrappy Beginnings

It’s everyone’s goal to launch with a polished, feature-rich product. I did the opposite. I talk about this in my last post, Minimum Viable Process.

A lot of tasks at With Jack are manually processed by me (generating quotes and binding policies). This is something I thought would be a hindrance, but has stood me in good stead with talking to customers and building a better experience. Every day I’m getting some form of customer feedback—good or bad.

I speak about launching with one polished feature in my talk, Idea to Execution and Beyond. For Jack that was the conversational interface. This was where I channeled my money and attention. There were other important parts of the customer journey that I launched without.

For example, With Jack launched without a risk questions form. I was sending people to Typeform to answer them.

Aside: The risk questions cause the biggest friction in With Jack’s customer journey. It’s a necessary part of buying insurance to see if your business is insurable or a liability. That you implement good practices like obtaining licenses for images you use, haven’t had any claims etc. That kind of thing.

Bootstrapping means moving slowly. This can be frustrating when it feels like everyone around me is raising investment and moving quicker. But I’ve really started to see bootstrapping as a blessing.

It means not building features for the sake of it because I don’t have the money to do so. It means taking one step at a time and using feedback to ensure what we’re building or the changes we make serve a purpose.

After launching with one, polished feature (the conversational interface), we turned our attention to the risk questions. It was a quick win. We stepped away from Typeform and built a self-hosted form. Nothing fancy. It looked like this:

The original risk questions form

The risk questions suck, but not answering them invalidates your policy. They’re the worst part of the process and embody everything I hate about insurance.

Legal jargon that nobody understands. Text that doesn’t read in plain English. Questions that aren’t tailored to your chosen industry. I can’t imagine any scenario where a web designer’s work could result in loss of life, yet that’s one of the questions.

Frustratingly, I’m not allowed to change the risk questions (at least not now. In the future I may have enough clout to work with an insurer to write them). This part of the process is where users drop off.

The customer journey starts on a friendly tone (the conversational interface), but ends on something different (the risk questions). Transitioning from a chatty tone to stuffy and corporate is never going to be smooth.

That wasn’t the only problem. Some of the users who did hunker down and answer the risk questions found the process confusing.

“Is it the final step?”

“How do I pay?”

The Three Key Problems And How We Addressed Them

  1. People felt thrown by the change of tone and copy.
  2. There was nothing to indicate this was the final stage of getting insured.
  3. Payments weren’t clearly explained. Customers would receive an invoice after they submitted their risk questions. This wasn’t obvious.

Somebody once bought insurance ‘accidentally’. When I sent them their policy and invoice, they said “I didn’t mean to buy insurance. I thought this was just another step in getting my quote”. Clearly there was a problem.

I was enjoying a weekend away with Naomi Atkinson when talking about this. (Yes, I have bad chat. This is why my friends don’t want to hang out with me.) Naomi is a designer, so she suggested redesigning the risk questions to address these common confusions.

People felt thrown by the change of tone and copy

As I mentioned, there isn’t much we can do about this at the moment. We did make one tiny change that helped. We switched the ‘yes’ or ‘no’ answers to ‘true’ or ‘false’. This framed the questions in a way that read slightly better.

This has worked well. We no longer have people misunderstanding the questions and selecting the wrong answer. Emails from users asking for clarification about the questions have reduced.

There was nothing to indicate this was the final stage of getting insured

Naomi pre-faced the form by outlining the steps.

  1. Confirm your details.
  2. Answer the risk questions.
  3. Choose how you’d like to pay.

We also changed the call-to-action from ‘Submit risk questions’ to ‘Get insured’.

Changing the call-to-action is the simplest fix, yet gives the form focus. Asking people to submit their risk questions poses more questions (“Why? What happens next? What am I committing to right now?”), but providing a button to get insured gives clear direction.

Payment options weren't clearly explained

We changed how payments are handled. Gone is the option to pay by bank transfer and we’ve limited it to Direct Debit. Users can now choose monthly or annual payments (I’d estimate 95% of customers choose to pay monthly).

Taking Direct Debit details makes it feel more like a check-out process. It’s eliminated any confusion around payment.

This is what it looks like now:

The redesigned risk questions form that improved sign-ups by 14%

These tweaks significantly reduced the drop-off rate.

  • Changing the call-to-action
  • Setting expectations by outlining the steps
  • Offering better payment options

It all helped increase the conversion of quote to purchase by 14%. Oh, and since implementing these changes nobody has ‘accidentally’ bought insurance.

There's Always Work To Be Done

The sticking point is still the copy. The nature of the questions and the legal wording means some people abandon the process without getting insured. This pains me because the benefits of being insured outweigh the temporary inconvenience when buying it.

It’s a case of getting a cup of coffee, putting on your headphones and spending a few minutes pushing through the pain. A small trade-off for the sake of protecting your business from shit like this and this.

With that said, Scott (the designer I’m working with) and I brainstormed how we’re going to address this with the next version. We think we’ve come up with a solution.

Another issue we’re tackling with the redesign is the feeling of abandonment once you buy your insurance. At the moment, the customer journey is optimised around quoting and buying. Once you become a customer it can feel like you’re being deserted. That is until things get hairy or your annual renewal is due. We’re tackling this next. More on that soon…

This is what I love best about building With Jack. Listening to feedback and implementing it, then watching the effect it has. Finding problems or inefficiencies and trying to solve them. Getting more freelancers insured.

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Minimum Viable Process

Minimum Viable Process

This post is available in audio format.

I’m probably the only person to launch an insurance company in 2016 without automated quotes. How very internet of 1996. This was because I had:

  • no existing book of customers
  • no indication I could build a succesfull company
  • no funding

It’s easy to see why insurers weren’t beating down my door, wanting to work with me. I’d have to start at the bottom and prove I could convert leads.

It had taken 2 years to get an insurer onboard. When the opportunity came to work with an insurer but manually process quotes, I took it.

It wasn’t perfect, but I was eager to launch. This was the quickest way to get With Jack in front of real users! Plus, I figured it’d only be a few months before I’d have an automated system. In the meantime I was happy to handle everything manually.

This meant checking for quotes in a CRM tool, logging into my broker panel, processing the customer’s quote and sending it to them. A minimum viable process.

The manual process of customer quotes

It did seem unthinkable that this would be the long-term solution. My goal was to build an insurance company with design and technology at its core. A manual process contradicted that and assumed the role of a traditional broker—not a technology start-up.

I had other concerns about not having an automated quote system:

  1. It was 2016. People could buy their insurance with the click of a button elsewhere. How was I making insurance accessible if it wasn’t instant? I was worried people would be put off by Jack’s “sit back and have a doughnut while we process your details” approach.
  2. I’d lose sales. Simple. Without an automated process that flowed cohesively, users would drop off.

Expectations wouldn’t be met and the conversion rate would suffer.

16 months and 190 customers later, there’s still no automated quote system. I didn’t expect to be manually processing quotes for this long, but it turns out it’s been a blessing.

The Beauty Of The Manual Process

High Conversion Rate

40% of the people who get a quote with Jack become customers! Conversions have improved over time, starting at 26% when I launched (I’ll share the tweaks that have contributed to the change another time). My concern about users dropping off was unfounded.

Understanding Customers

I’ve spent the past 16 months having customer conversations. Most insurers have few touch points with customers and it’s usually in negative situations. Such as when a payment has failed or a customer makes a claim. Because they’re mostly dealing with customers in sensitive situations, this contributes to the negative connotations people have about insurance.

Let’s talk about customer conversations.

I’ve manually processed each of the 190 sales. This means I’ve conversed with 190 of the very people I’m building With Jack for. That’s invaluable! I’ve learned:

  • Where customers come from
  • Who referred them
  • Why they signed up
  • What they thought of the experience—good and bad
  • Their motivations for getting insured

Forming an understanding of this helps me improve the service and understand how and where to market it. This has been crucial in informing my decisions. It’s also influenced the copy and design changes we’re making.

Lastly, it’s enabled me to connect and build deeper relationships with customers.

Don’t get me wrong, not everybody wants to engage. Some people prefer to sign up with as little interaction as possible. They want to check a box, be on their way and don’t care who is powering the experience for them.

(Despite having to manually process everything, it’s possible to buy a policy via Jack without interacting with me personally.)

But for many—and the type of customer I’m hoping to attract—they want more from their insurance. They’re happy to engage and shape With Jack.

After the fear of launching without instant quotes, it turns out people are OK with the human element. The proof? 40% of people who get a quote convert to customers and 87% choose to stay come renewal time. (The 13% churn is attributed to freelancers taking up full-time employment, winding down their business or relocating abroad.)

Customer development has been the most valuable thing we’ve done when it comes to moving our product and company forward, and I wish we would’ve done more of it in our early days. — What To Do If You Didn't Get Into Y Combinator

When I launched in 2016 I wasn’t thinking along the lines of customer development. I didn’t even know what that was. The manual process was simply the quickest way to ship.

16 months later and I echo Alex’s comment above—customer development has been the most valuable thing to inch With Jack forward. Speaking to customers has been as a direct result of having to manually process quotes.

The Downside Of The Manual Process

I can never be too far from a computer.

This month I enjoyed my first holiday since launching With Jack. A Canary island off the coast of West Africa, 24 degrees celsius in January. The catch? I had to carry my laptop everywhere.

I onboarded a customer on the airport bus. I sent quotes by the poolside. I answered emails over dinner. Most impressively, I emailed somebody their quote from on top of a volcano! Amen for tethering.

The view from the volcano

Fun fact: Volcano quote converted and was the biggest sale I’ve had this year. It was definitely worth it.

I did get stick for being on my laptop. A lot of the people I was holidaying with work 9-5 and have the luxury of switching off. Being my own boss meant I couldn’t disconnect completely. If quotes came in, they had to be dealt with.

This is the downside of manually processing quotes, but it’s a small price to pay and is temporary. I’m at a stage where every sale is crucial.

Automation Is Coming

Instant quotes. They’re coming. Scott’s in the process of designing the customer journey and the insurance paperwork is being completed.

I’m aiming to keep an element of human throughout. It will be a balancing act and I won’t get it right from day one, but I’ll iterate on it.

With a customer journey that’s scoring a 40% conversion rate, I am afraid the automation will negatively affect that. However, from the customer conversations I’ve had I know that I’ve lost sales due to not having instant quotes. Existing customers have also expressed their preference for automated quotes when shopping for insurance. It will also allow us to experiment more with the customer journey.

What's The Point In All Of This?

I have two takeaways.

  1. Launch with the simplest version of your product or service (a small experiment).

    At one point I’d have considered delaying the launch of With Jack until the system was automated. Not because I was deterred by the work involved in manually processing everything, but because I believed customers would be discouraged by it.

    I was wrong. The idea should always be to launch with the simplest approach, speak to customers and learn. Sometimes that means manual processes!

    An MVP is a process that you repeat over and over again: Identify your riskiest assumption, find the smallest possible experiment to test that assumption, and use the results of the experiment to course correct. — Minimum Viable Product Process
  2. Build customer development into your business from day one.

I can’t stress this enough. With Jack’s growth has been slow and steady—this is the nature of bootstrapping. But long-term I’ll have a competitive advantage because of these conversations.

Speak To Everybody—Customers, Potential Customers and Lost Customers

40% of people who get a quote convert to customers, but that leaves 60% who don’t. I don’t ignore them, even if it does mean having uncomfortable conversations about why they didn’t sign up.

It’s trickier getting a follow-up from lost sales. They’re not invested in the service, so likely won’t take the time to provide constructive feedback.

The direct approach has had little success for me. A final email to ask why they didn’t sign up mostly goes ignored. I’ve had more success using a survey tool (I use Iterate). I still won’t get a high response rate, but it’s worked better than email. I create a short survey with 3 questions and stress it’s anonymous.

When I send a link to the survey, I try appealing for feedback on a personal level (“As a one-woman startup, this feedback really helps and goes into shaping With Jack”).

Here’s some of the feedback I’ve been getting:

Using Iterate to collect lapsed user feedback

Decided not to take out insurance policy

That in itself isn’t helpful, but they elaborated on the question that follows it (What can we do to make With Jack better for you?). From their response I can gather they were happy with the customer journey, but were shopping around and choosing a provider based on price.

My client insisted on a ridiculous level of cover

I see this a lot. Their client gave them a boilerplate contract they also use for big companies. It demanded £10,000,000 of professional indemnity, public liability and employers’ liability! This isn’t an uncommon scenario and freelancers should push back on those terms. From this feedback, I could write a blog post about what to do when your client requests a high level of cover.

I needed worldwide cover

This is interesting. With Jack can arrange worldwide cover, but this indicates I haven’t done a good job of being clear about that. Now I have something actionable to implement; do a better job of highlighting this feature.

Manual Processes FTW

Waiting until With Jack was automated would have delayed my launch and cost significantly more to build. Instead I was able to ship quickly, start earning money and learn from customers immediately. With the automated system, I would have missed out on a lot of insights.

Switching to instant quotes means missing out on conversations at this point in the customer journey. That’s something I’ll miss. I believe this is what’s helped me bootstrap With Jack from the first 20 users to (almost) 200.

I hope automated quotes will take me from 200 to 2000.

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2017: Year In Review

2017: Year In Review

My last Year in Review was written when With Jack had barely launched. I was getting to grips with what tools to use, where to find customers and even who my customers were.

Now I’ve been building With Jack for over a year.

Spoiler: It doesn’t matter how far into the journey I am, I’m still figuring things out! With that said, With Jack is definitely growing up.

I’ve found that each year has a theme. 2015 was all about filtering out distractions and focusing on my goal with insurance. 2016 benefited from my laser focus in 2015 and I finally launched With Jack. 2017 was slow and steady improvements. Iterating and inching forward. One foot in front of the other.

This is my personal and professional reflection of 2017.

Q1—January, February, March


The year started badly. I was celebrating my 30th birthday in Geneva when my house was burgled. Over £5000 worth of belongings were stolen. Fortunately I had insurance.

Everything was replacable, but the emotional impact of having a stranger in my house, touching my personal possessions was… disturbing.

When I returned from Geneva I found a lump on my dog’s leg. Cue a lot of anxiety and visits to the vet with Indie. The bad news: it was a cancerous lump. The good news: I caught it quickly.

What followed was an operation, a difficult recovery, another lump and a lot of stress.

Indie recovering in the sun

The year improved after a rocky start. One highlight of January was my profile in The Sunday Times. Indie and I had a photo shoot and were featured on the cover of the business section playing a game of pool (she won). I was also profiled in The Evening Times in March.

Q1 saw big changes to With Jack! I rolled out new products to the quote system, almost doubling my average commission. I worked with Naomi on improving the onboarding experience and removing friction. This took my conversion rate of quote to purchase from 26% to 40%.

March came to a close with Naomi and I escaping to Loch Fyne for a few days of relaxation.

Naomi at Loch Fyne

Q2—April, May, June

In April I traveled to Uist—an island in the Outer Hebrides—to watch a close friend get married. Shawshank and I have been friends since college, so visiting her home town of Benbecula was overdue.

It was an experience on many levels. The propellor plane, barren landscapes and slow pace of island life with the juxtaposition of a wild wedding. Those islanders know how to party.

What an island wedding looks like

May is when things ramped up. I travelled to Southport to film a segment of Right on the Money for the BBC. This was about earning extra income from a hobby like I do with photography, which has enabled me to fund the development costs of With Jack. Being on TV is scary.

I celebrated reaching 100 customers. I’d love to have ended the year hitting the 200 milestone, but I’ll be about 20 customers short. I’m still giving myself a pat on the back for reaching this point manually submitting quotes and as a one-woman, bootstrapped startup.

Q2 also saw me apply to join an accelerator, Ignite. This has been a highlight of the year (even if I didn’t get accepted into the programme). The amount of knowledge I’ve accrued has been invaluable. I’ve met interesting people and got a better grasp of what I need to do with Jack. I can thank this experience for a lot of what I’ve learned this year.

The first Ignite offsite in Newcastle

I finished Q2 by building in support for more professions. 70% of With Jack’s customers are made up of the initial audience I launched to (designers and developers), but I started to get interest from photographers and marketers. Improving the experience for them has encouraged more sign-ups.

Q3—July, August, September

Q3 was quiet. I continued attending Ignite’s monthly offsites in Manchester, London and Edinburgh and chipping away at With Jack. Insurance sales dipped in the summer, but I’ve learned this is a pattern I can’t do much about.

In August I started a YouTube channel. My only plan with this was to commit to an upload every week and be transparent (a contrast to the “We’re always killing it” culture). However, my plans will be changing for the channel in 2018. Stepping away from weekly videos, but creating meatier content.

Q4—October, November, December

In October I did something I’m proud of. I completed a half-marathon! It was sprung upon me 2 weeks before when a friend pulled out of the race. With minimal training I got around the course in 2 hours and 30 minutes. It was the farthest I’ve ran. I am not a runner. I lift weights.

Speaking of weights, I also managed a 90KG deadlift. That’s a personal best!

The latter part of this year has been great for fitness. Joining park run and taking up circuits has meant getting back on track with exercise.

After the half-marathon I flew to Bristol and gave my talk, Idea to Execution and Beyond, at Web Dev Conf. Public speaking still terrifies me, but I’ve vowed to continue practicing. Once back in Glasgow I delivered the same talk at GlasgowJS.

Speaking at Web Dev Conf

The highlight of Q4 was Scott Riley visiting Glasgow. This was the beginning of us redesigning the customer journey for the self-service quote platform (in other words, instant quotes!).

I didn’t expect to be manually submitting quotes this long, but it’s given me an opportunity to speak to my customers. When most insurers think customer development is a pop-up survey upon exiting their site, I’ve had some eye-opening conversations that have directly shaped Jack.

An unexpected addition to revenue was event insurance. At the end of November I tweeted about offering insurance for digital conferences and meet-ups. Within a couple of weeks—without building it into the system—I had sold 3 policies. I think I just validated something without writing a line of code!

Last Year's Review

My big goal is to punch an insurer’s rates into my system so quotes and cover are instant. I hope I can make that happen in 2017, but it all depends on the volume of business I continue placing.

This is happening. As with everything in insurance it takes time. Forms to be filled out, applications to be submitted… But it’s happening.

I also wrote a separate post with my goals for 2017. How did I do?

  • Add more cover features to the quote system (Nailed it)
  • Build a dashboard for customers (In progress along with the self-service quote system)
  • Create a referral scheme (It’s basic, but customers are using it)
  • Double the number of policies I’m selling (Nope)
  • Run a half marathon (Woah, I totally did this)
  • Sit my next insurance exam (Currently studying. It’s boring)
  • Do a photo project (Only if you count ‘My Weekend In Photos’ tweets. I generally took more photos and kept my photo blog regularly updated, so I count this as a win)

The goal I stumbled with was doubling my sales. Every time activity picks up and I think it’s the start of a trend, there’s a period of stagnation. In fact, With Jack’s growth looks a lot like the image below (taken from Navigating The Long, Slow SaaS Ramp of Death).

This is how my sales look

I’ve spent the latter part of this year learning how to convey the value of insurance and describe what With Jack does without saying, “We sell business insurance”.

This is where I’m currently at, but I’m constantly iterating.

The Problem

44% of freelancers will be stung by a bad client. This can set the freelancer back financially and be emotionally taxing.

The Solution

With Jack helps freelancers get the policy they need to protect them financially and legally if that happens. We’re on your side and offer emotional support, so it doesn’t feel like you’re facing the problem alone.

The Reward

Freelancers are free to focus on the important stuff—securing that next project and doing great work.

The Pitch

44% of freelancers will be stung by a bad client. With Jack helps freelancers get the policy they need to protect them financially and legally if that happens, freeing them up to focus on the important stuff.

Nailing Jack’s messaging should improve sign-ups. That and building the self-service platform!

It has been a struggle bootstrapping. I haven’t invested anything into With Jack beyond money I’ve earned photographing weddings. I do feel like I’m moving slowly—from developing product features to growing the company.

Bootstrapping requires a lot of patience. When you see others moving quicker or having more resources, practicing patience can be challenging. But I’ve thought a lot about this topic and bootstrapping feels right.

Other things I did that didn’t fit anywhere else:

  • Built a ‘What insurance do I need?’ tool
  • Attended Startup Summit, Turing Fest, Startup Grind, Virgin Startup, Tech Masterclass and GAB
  • Visited Newcastle, Manchester, London, Bristol, Southport and Cambridge for work
  • Watched lots of my friends have babies (3 had babies, 1 is pregnant)
  • Got back into drumming. Once a week I book a studio for an hour and practice
  • Read some books. Business for Punks, Shoe Dog, Sprint, Lean In, Creativity Inc, The Subtle Art of Not Giving a Fuck, and Confessions of a Public Speaker.

Cold, Hard Stats

With Jack’s ending 2017 with the following stats:

  • 25,366 Visitors
  • 176 Customers
  • 40% Conversion Rate
  • £56,000+ Gross Premium Written
  • 87% Renewal Rate

I’m doing something right. 40% of quotes become customers and 87% of them choose to stay with Jack come renewal time. What I’m lacking is volume. I’ve known this all along, and it’s a problem I’m not yet sure how to solve.

Looking Forward

Even though 2018 is only a few days away, I haven’t given much thought to it. I’ve been wrapped up in what’s happening right now. I’ll possibly write down my goals once I’ve given them some more thought.

I do know I’m itching to be more creative; with the content I write, videos I produce and photos I take. I do know I have another year ahead of being laser focused on building With Jack.

It’s likely much of the same as 2017, but with more experience, more resources (I have 176 customers and a renewal rate of 87%. That’s a decent chunk of recurring revenue) and continuing to iterate.

Oh, and hopefully no more vet visits or break-ins.

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Why I'm Bootstrapping

Why I'm Bootstrapping

At some point this year I started considering investment. The initial build of With Jack was funded with my own money (money I’d earned photographing weddings at the weekend).

I liked the idea of bootstrapping. The investment scene mystified and intimidated me, but bootstrapping had its downsides. It meant taking short cuts, iterating slowly and being limited with marketing experiments.

Taking Short Cuts

A lot of With Jack’s tech was built on a shoestring budget. Some of it’s a quick fix to get the job done. It’s fine at the moment with just me working on Jack, but once I grow it’ll get complicated and have to be reconsidered.

Iterating Slowly

I don’t have the budget to match my ideas. That’s frustrating. When bootstrapping you have to ruthlessly prioritise. You don’t have the capital to explore every idea. Even the process of iterating on one feature is slow. I’ve focused on the onboarding process, but there are features for existing customers I’d love to build.

Limited With Marketing Experiments

Most of With Jack’s customers have come from organic search, word of mouth and referrals. Not having a pot of cash to dip into means being limited with marketing. I’d like to experiment with conference and podcast sponsorship, but it isn’t cheap.

My numbers have been consistent from day one. 10-12 sign-ups a month. Retaining 83% of customers come renewal. But I hit a plateau. I didn’t have the capital to reach more people and With Jack’s product wasn’t evolving as quickly as I’d like.

That’s when I applied to join an accelerator. A £25,000 cash injection with connections to the investment scene, meaning there was the option to raise more if needed.

(At the crux of it, I was excited to tap into the mentor’s experience and meet like-minded people. That was my priority and the accelerator delivered on that front.)

Truthfully, I was never fully committed to the idea of investment. Even during the application process I wasn’t sure if it was right for me. It was more of a, “Let’s dip my toe in and see what happens” vibe. But before I knew it, I had drank the Kool-Aid and got sucked into startup mentality.

“A lifestyle business isn’t good enough.”

“You have to think bigger and be more ambitious.”

“Not getting funding means you’re not good enough.”

“You need to disrupt an existing business model.”

These were just a few of my thoughts.

As well as the cash injection I wanted validation. Getting investment was like somebody saying, “I believe you can do this”. After years of insurers rejecting working with me, my fragile ego craved validation.

But I didn’t get investment.

After the initial disappointment I felt OK about it. No, really. I trust the accelerator. I respect the people who made that decision. I understand why they passed on investing. It wasn’t right for them… and in hindsight it wasn’t right for me.

Side note: You may be wondering why I didn’t get investment. I think it was down to being a solo founder, not solving a big enough problem and being unclear on where the £25,000 would go. I’m sure there were other factors, but these are the obvious obstacles.

I had no desire to apply for other accelerators. I’d been on the fence about investment, so when it fell through my thoughts turned back to bootstrapping.

Why I'm Bootstrapping

I realised I’d prefer turning my attention towards getting 1000 true fans.

I realised the funding process isn’t for me. I’ve spoken to my friend, Cally, at Mallzee about this (they’ve raised over £4 million). Taking time away from work and exhaustive travel wouldn’t make me happy. I like working from Glasgow, having my routine and hanging out with my dog.

I realised I want to figure things out in my own time and retain control, instead of having strings attached and scaling quickly to satisfy investors.

I realised I want to focus solely on my customers. Not on VC’s or getting wrapped up in the insurtech bubble. To be laser-focused on the people that will make With Jack profitable.

Above all else, I realised I didn’t want to disrupt an industry. I want to pick a small corner of the web that I can call mine and build something great.

That’s it.

What Do I Want To Achieve?

Building something profitable and of value for thousands of happy customers.

I still have an internal struggle. I wonder if I’m taking the easier option (although nothing about this journey has been easy). I feel bad about myself for not maxing out my ambition. Especially as—with no family or children—I’m in a position where I can take more risks.

But then I go back to what success means to me.

Success is crawling into my bed at the end of the day feeling creatively satisfied and challenged. Currently, I feel that way most days.

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A Week In The Life Of…

A Week In The Life Of…

I enjoy reading other people’s ‘week (or day) in the life of’ posts to get a glimpse into their routine, so I micro-blogged every day last week. No week is the same when building a business, but how did last week look as a one-woman, bootstrapped business?


Monday and Friday are my favourite days of the week. I’m excited about the week ahead. There are still a lot of unknowns at this stage in my business. Whilst that would scare some people, I see it as an exciting time.

This particular Monday was interesting as it began with a shot of champagne. This doesn’t normally happen, but one of the businesses in my co-working space secured money to launch their product.

I made an ‘Insured Via’ badge for our customers. This is a badge they can display on their site to show clients, potential clients and visitors they’re professionaly insured. To my surprise a customer immediately adopts it!

A proof of insurance badge

I had a call with From Scratch who is working on With Jack’s copy. The current site doesn’t convey the value With Jack provides freelancers or the problem we solve. Sabine is helping me hone my message (a piece of advice drilled into me from Ignite).

I also finished watching the last of the InsurtechCon videos on YouTube. I watched every one of them to get an idea for where the UK insurance industry is headed.

In the evening I attended Tech Masterclass at Glasgow University. Rachel Evatt, who sold her startup to Skyscanner, was speaking about creative courage. I get a lot of value out of these masterclasses and use them as an opportunity to ask questions and seek advice.


I have a few copies of Learn From Great Design in my arsenal, so decided to run a giveaway through With Jack. My thinking here was purely traffic-related. A quick win (or so I thought) to get more eyeballs on the site.

It took time to get the landing page right, but one of the Slack groups I’m in provided critique (thanks!). For the amount of effort I put into this, however, it was a total flop.

Today was also about budgeting. I sent From Scratch, my copywriter, an email with the budget for writing With Jack’s copy. Budgeting is hard at this stage. I’m bootstrapped, early stage and a one-woman band, but I’m also open and transparent about money with any of the freelancers I work with.

One of my customers has built a forecasting tool. We worked out a special deal for With Jack customers and added it to the growing list of benefits. Having this kind of collaborative relationship with my customers makes me happy.

Another sociable evening. A photography group I’m a part of has their ‘end of wedding season’ party tonight. We meet in a pub, drink a few rums and talk shop.


Gah. Today I woke up with sore throat and cold symptoms so I worked from home. I wasn’t as productive as I am in the office and mostly used today for research purposes. There’s a new direction I’m flirting with for Jack.

For someone who likes technology and design, I’m not sure why it took me up until now to sign up to Tide—a business current account packed with powerful tools. First impressions: Why have I been using my crappy, dinosaur bank for so long?

I sent some cold emails today. I haven’t had any success with this so far, but I only do it when I genuinely stumble upon a business I’d like to work with and think would be a good fit. It’s probably strange for them to receive an email saying, “I really like your work. Let me arrange insurance for you!”.

Tonight I was supposed to attend GAB, my favourite meet-up. Feeling sniffly I decided to stay indoors. Instead I worked on clarifying my message after listening to How to Tell People What You Do in 3 Easy Steps.


Out of the office today. I’m visiting my old high school in Dunoon! Since leaving school 14 years ago I haven’t given much thought to education. That was until a couple of weeks ago when I gave a talk at my old school.

It made me think how powerful it is to have a positive impact on even one student’s career or attitude. Today I’ve returned to judge the YPI final alongside ex-pupil Sam Coley. Sam now runs a startup TickX.

The winners of YPI!

Apparently my old school has a poor uptake of girls with computing, so I’d like to get involved in addressing that.


I’m currently going through the Ignite programme. Well, kind of. I didn’t get investment or fully onboarded, but I’m attending the monthly off-sites in exchange for creating content for them. Today I edited and uploaded my latest Ignite video, so I’ll be sharing this on my YouTube channel come Monday.

I’ve been working with Catch Media, another of With Jack’s customers. Catch Media is managing my Twitter and Facebook ads, so I sent them copy and assets. It’s scary delegating tasks (and spending the money), but it frees me up to focus on other things. Everybody keeps telling me I can’t do everything alone, so I’m taking their advice onboard.

The Learn From Great Design giveaway came to an end. What a flop. I have 10 copies and only 5 people entered—so they automatically win. What should I do with the 5 remaining copies?

I end Friday with a few boring tasks. Catching up on email, going over analytics, sending payments to suppliers.

Now it’s time for mulled wine at the Christmas market.

Mulled wine at the Christmas market

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