513 words • 3 min read

I still personally email every new Pilot customer and offer to get on a call with them.

I mentioned this to some startup founders, and the general reaction was “Wow, really?”—and further surprise that, worse, I do it entirely manually. There are no bots or automated email sequences behind the scenes. It’s literally just an email from me with a scheduling link, and I click send.

This reaction is an example of a prevalent founder behavior: a tendency to think that everything needs to be made scalable—and therefore you either need to (a) simply not do unscalable things, or (b) build processes that let you do them more scalably.

It’s easy to see how you get there: you’re planning for growth. You’re planning for scale. Surely you should be putting processes into place for everything now, so that you’re ready to grow later, right? This type of optimization usually feels productive, which is why it’s such a big trap—especially because the underlying task is typically one that feels tedious or boring.

The problem is twofold: first, building the scalable or automated process can be very time-consuming, and it’s easy to spend more time building the process than you’ll actually ever save by using it.

But more importantly, it locks in an experience before you’re sure it’s right. You’re always learning about who your customers are, what they care about, what their requirements are, etc. As soon as you commit these to a process, you become less flexible.

Pilot has thousands of customers—making us the largest startup-focused accounting firm in the US. At some point, I will not be able to get on a call with every customer. But we’re not there yet, and the ROI of doing the unscalable thing is very clear.

The cost of my doing this is well-understood and easily bounded:

  • I schedule each call for 15 minutes.

  • I spend no more than an hour a day on “welcome to Pilot” calls.

  • If I’m especially busy, I remove call slots for that particular day or week.

And the benefit of doing these calls is very clear:

  • It helps me understand who our customers are in a really visceral way—in a way that I wouldn’t get by just reading the CRM notes.

  • It’s a nice “surprise and delight” moment which helps to 10x the customer experience. This increases both brand perception and customer retention.

  • In the unlikely event that one of these customers runs into problems down the line, they have an open invitation to reach out to me directly, rather than angrily tweet about it.

  • Only 20% of the people I reach out to actually take up the offer, but 100% of them know I’m personally committed to making sure their experience is good.

Scalability is not the be-all and end-all of running a startup. One of the biggest advantages that a startup has over a larger company is that it can do unscalable things and still be effective. It’s a mistake not to take advantage of that.

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