A few months ago I launched my automated quote and bind system. Something I've been building for 6+ years. Yes, 6 years is not a typo. One day I'll share what it takes to build software in a heavily regulated industry. For now I want to talk about a different challenge.
Migrating my existing customers and how I plan on making that transition as successful as possible.
The opportunity (and the problem)
The automated quote and bind system is a game-changer for new sign-ups. Early stats are promising with a 40%+ increase in new customers.
This is because freelancers shop for insurance in evenings and on weekends. Prior to this launch I was unable to meet those needs because, well, I don't work 24/7.
I tried working all hours when I first started but learned it's not sustainable. It leads to burnout and silly mistakes. This system fixes that. It helps me convert a lot of the sign-ups I've been missing out on.
However, what convinced insurers to back this platform was the existing business I could promise. Having arranged insurance for over 2000 freelancers since launch, it made buying into this less of a gamble. So the pressure is clear. I need to migrate as many of my existing customers over to the new system as possible.
If you're new here and need more context, the old system I used belonged to the insurer. It required me to manually process every quote, renewal, mid-term adjustment and cancellation. It's admin that took away from driving real improvements to the products and services we offer. It also meant that—in the 9+ years I've been working on With Jack—I've have never had time off. This podcast I recorded in 2022 goes into more detail.
If improved conversion rates, less admin and better product development is the opportunity, then what's the problem? When we spoke to customers in the build-up to launch the reaction was… underwhelming.
Challenges I expect to face
I know there will be surprises post-launch, but after 9 years of manually sending renewals I have a solid idea of what friction I can expect.
- customers not opening the migration emails
- domains expiring leading to bounced emails
- procrastination
- aversion to the increase in price
- having to complete additional information, like answering the risk questions and re-entering payment details
- expectations that the insurance auto-renews, leading to customers not taking action
Fears I have
A lot of my fears overlap with the challenges above. I'm worried I'll lose a chunk of customers. If I can't demonstrate this new platform works, there's a real risk the opportunity could be taken away.
We're asking people to answer new risk questions, re-enter payment details and accept a price increase. With each additional piece of friction, the likelihood of someone dropping off increases.
But there are reasons to be hopeful.
- There’s a core group of customers who trust With Jack
- In the focus group people expressed their understanding that companies change and there will be advancements in technology
- Switching providers isn't frictionless either. If anything it's worse
So I'm hoping people stick with what they know instead of starting again somewhere else.
My first hire for the biggest migration in With Jack’s history
As we neared the end of the build phase and started prepping for launch, I knew I needed help.
I've been working 'in' this for too long. I'm looking at this from the perspective of how it impacts me and I'm bringing a lot of emotion into it. Because of this I decided to bring a communications consultant onboard.
They could help prepare the clearest comms for what this means for customers, picking up on issues that I didn't consider.
Hiring a communications consultant was inspired by the issues I saw the insurer face when they migrated customers to a new payment system.
They'd sent emails with the title, "Your direct debit has been cancelled". Nothing had been cancelled. They’d just migrated direct debits to a new system. We were inundated with support requests and panicked phone calls from customers worrying their insurance had been cancelled.
All of this extra support was avoidable. That painful experience stuck with me and lead me to bringing a communications consultant onboard for our migration. It's been one of the best decisions I've made!
Pulse surveys, focus groups and innovation sessions
After reviewing candidates (and trusting a recommendation), I hired Vicky Gu—a strategy and brand consultant based in Brooklyn.
Vicky started with pulse surveys to gauge the general feeling towards With Jack.
- What are we doing well?
- What's important to customers?
- What improvements would excite them?
The results were not what I wanted to hear. The features we'd spent months building—like educational content and self-service tools—scored low. Customers voted lower prices as the thing that mattered the most to them.
The prices are going up with the new platform. Not a good start!
We then moved onto the focus groups which involved video calls with small groups of customers. The feedback was consistent. "I don't understand how this benefits me. I like the way things are. What if I choose the wrong cover?".
This isn't the reaction you want pre-launch, but there was a bright spot. People trust the With Jack brand. People trust me.
Our takeaways from the surveys and focus groups were:
- Put a pause on fleshing out the education stuff. It's clearly not important so what's the point in investing resources into it for launch
- Reassure customers that the team isn't going anywhere. We're still available to help with everything, we're just giving you the tools to handle the routine stuff
- Focus hard on the benefits. Yes, there is a price increase. But we've reduced and in some cases removed the excess, introduced new (lower priced) levels of cover, launched new products and brought the legal advice in-house
Once we created the email sequence, FAQ and demo page, Vicky message tested the material again.
This time the reaction was more positive. Feedback implied we were able to alleviate some of their concerns. At this stage we started to hear more positive responses, but no matter the prep we put into addressing concerns I knew a number of surprises would emerge post-launch.
As an aside, I wouldn't have had the drive to do focus groups because I hate cluttering my work days with video calls. This is one of the blessings with having Vicky in this role.
I also feel that as a founder I would have picked out the feedback I wanted to hear. I think it's called confirmation bias. Having someone neutral distil the feedback down removed any of the bias. This is how we landed on the core message: "the team isn't going anywhere—we're just giving you the tools to handle the routine stuff".
Launch strategy = remove the element of surprise
It was important the migration didn't come as a surprise to customers. This was one of the goals I set in the brief with Vicky.
By the time customers receive their renewal reminder they should be:
- expecting to be migrated to the new system
- aware of what it means in terms of product changes and tools they'll now have access to
- anticipating having to take some action to set up their account
This meant preparing:
- a sequence of emails
- launch videos
- a demo of the new system
- FAQ
- migration landing page
Vicky left no stone unturned!
Alongside how thorough we've been with the material we've created, one thing that did give me hope was the reaction to our 9th birthday post.
Vicky suggested doing a social media post to celebrate 9 years in business, hinting at a big product update. The supportive comments on LinkedIn and Instagram from customers gave me hope there's enough brand loyalty for them to go on this next stage of the journey with me.
The other positive signpost was the reaction to the first email from the renewal sequence. It had a 75% open rate and lots of replies from customers rooting for me. Some of my favourite compliments included:
"It's great to see your company grow and evolve"
"Looks like an awesome upgrade."
"Always good to see you going from strength to strength."
After the mixed feedback from the focus groups, it was reassuring to have encouraging pats on the back!
This is my biggest achievement to date
6+ years on any project is a long time and life didn't exactly pause while I was working on this.
In that time we've seen a global pandemic, the loss of my mum, Rangers winning their first league title in 10 years, a cost of living crisis, falling in love with James, war, finding out we're pregnant with twins, miscarrying the twins the week I was meant to launch. It's been… a lot.
I've had a whole range of emotion throughout those 6 years in regards to this journey. Sometimes all of them within the one day.
Desperation. At the start of this process in 2019, I had a tunnel vision of building software in the insurance industry.
Apathy. There were many points throughout the 6 years I lost interest, felt burnt out or started to doubt whether this would ever happen.
Fear. When my coverholder status was approved in December '24, fear set in. This was actually happening but the timing couldn't have been worse. It was the final few weeks of my mum's life. I started questioning whether this was even important to me.
Excitement. A matter of days away from launch and fear was replaced with excitement about how this could look for sign-ups. Having a new project to nurture. The freedom it could afford me (once renewals were migrated and bugs ironed out). The opportunities it opens up. The hope that I can finally build the business I've always wanted to.
Apathy. Again. Miscarrying the twins the week I was due to launch put work into perspective for the second time that year. Motivation dwindled. There was an emotional and physical recovery that followed.
Pride. I am proud of myself for getting to this point. I don't know many people that would have dug in for this long, especially with no guarantee it was ever going to get over the line.
Expectations. What's considered a successful migration?
Despite putting a ton of work into the migration process the reality is this is a transition period and we will see a loss of business. It's a total guess but—from looking at how many customers ignore renewal reminders historically—I wouldn't be surprised if only 30% of our existing customer base migrate.
Out of the 117 renewal reminders we distribute each month on average, I'd be delighted if anything above 50% migrated to the new system. I'd consider that a win—especially as we're seeing more new sign-ups to balance the loss of existing business.
But it's not just about me. It's about the insurers that have put their faith in me. I know they want a higher conversion. Probably closer to 80%.
My hunches have been wrong before. When Covid hit and we started losing customers, I anticipated churning 70% of our business. In the end it was closer to 25% and most of those came back once they realised the world was still turning.
So we'll see. What I do know is we've built a good system and put in the groundwork to make the migration as painless as possible. I am good at my job and have conviction in myself. Whether this works or not, it was something I needed to try.
If I stayed in my bubble of manually processing everything I'd regret not seeing what I was capable of building, because not having to do the routine stuff frees me up to develop new products and services. I've always wanted to aim higher but the old system was a constraint.
Oh, and I'm human. There is only so much time you can give something without taking a break. This system gives me a freedom that I haven't had for the 9+ years I've been building With Jack. A freedom to take breaks, recharge and start trying for a family.
There's a long 12 months ahead
Because the focus groups highlighted anxiety about getting things wrong when migrating, I decided to handle most of the legwork myself. The more steps I can take on behalf of the customer, the likelier they are to migrate.
This means the migration is very hands-on for me. I'm setting up each policy on the new system manually with their existing details and cover options. This will be something I do every day for the next 12 months so that the only thing the customer has to think about is answering the risk questions and selecting their payment method.
We agreed to start the migrations on the 1st of March… the day before I went on what was meant to be a relaxing holiday with my boyfriend! It turned into more of a "working from a warmer climate" trip than a break. However, this big stretch for the next 12 months could be what sets me up long-term.
If this pays off it will lead to me being able to take some proper time off. One day. Eventually. Soon. Hopefully.
We're now 23 days into the migrations. I'm going to give an update once we've got a whole month or two of data behind us.
