I decided to hire a person I knew was perfect for the job… I knew nothing about sales at this point, but when you are 23 such insignificant detail can hardly stop you.

Salespeople have gained a bad reputation over the years.

Typical consumers will automatically shut them off when they hear that they're from that company selling this product.

As a result, I’m in the fortunate position of being able to get a sense of the cadence of those calls and a feel for the entire sales process from lead generation to closing.

What I’ve learned from those years of experience is that the closest analogy for selling software is dating.

We learn a lot through dating, because it allows us to gain experience through trial and error.

This search is similar to the process of finding the right business partner. Our prospects spend a lot of time and energy researching, reading, testing, and trying to cut through the sales jargon to find the right solutions.

Dating can be a long and somewhat grueling process, but it’s necessary in order to find the right person.

It sometimes includes dealing with deception, lies, and broken promises.

The dating analogy has applied to countless situations with prospective clients over the course of my five-plus years selling software.

For example, I remember a client several years ago where we had engaged in an extended pilot (which felt like dating over the span of several months), but then we quoted them a price for full deployment and they balked (like suggesting that we stay in and watch sports every weekend).

I want to begin by acknowledging that I am not a salesperson.