How Startups Sell Without a Sales Team

Before you automate sales, understand your human customer

7 min readApr 12, 2021

It’s every founder’s dream, right? You wake up in the morning, go to a dashboard, and bask in the sweet glow of how much product you sold yesterday.

But it’s more likely that a company’s leadership team wakes up in the morning and waits for the customer relationship management (CRM) system to get updated. And waits. And waits. And then, by the end of the day, they realize nothing was closed. Or maybe it was and it will all come cascading in on Friday afternoon.

One of the most difficult functions for any company to put trackable numbers around is the sales funnel. How many prospects are in the funnel? How many of those are actually qualified prospects? What’s the likelihood the prospects are closed at each level? Have any of them closed? Why aren’t they closing?

The usually vague answers to these questions are even more vague when your company is a startup. That lack of clarity screams for automation.

All selling can be automated, but not automatically

If car dealerships can replace salespeople — and I’m looking at Carvana, TrueCar, and the like — any startup can automate the sales process of any product. But automated selling doesn’t happen automatically.

The proliferation of two-sided markets (2SM) makes it seem like any product or service can be transacted through a digital middleman, one that takes a much smaller cut of the sale and returns those savings to both the customer and the vendor.

But for every 2SM that gets traction, there are tens or hundreds more that don’t. And the reason for that is very simple to state but very difficult to overcome.

Sales is like selling used cars, not Diet Cokes

People, especially entrepreneurs, like to think of sales as a vending machine (looking at Carvana again), with a zero-friction experience. The customer points to what they want, they swipe a credit card, they receive the product and smile. The hardest part of the process is getting your hand back out of that thief-proof door at the bottom.