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.

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.)

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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.

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.

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!

Minimum Viable Product Process

1. 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:

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.