Why Being Clueless Can Be a Great Thing

How hiring our first salesperson led me to recognize that cluelessness is at the heart of entrepreneurship.

We entrepreneurs can be clueless at times, and that is okay. In February, I interviewed candidates for the first sales position at my company, JotForm. I have never been a salesperson, and I have never worked with one before. I may as well have been recruiting nuclear scientists, interpretive dancers or blacksmiths.

But my inexperience was a gift. It led me to recognize that cluelessness is at the heart of entrepreneurship, and how we deal with that cluelessness defines our company. With that said, I want to share how I was able to get the most out of my ignorance.

Cluelessness as an invitation

Entrepreneurs usually experience cluelessness as a result of or as a harbinger of change. For example, my company typically focuses on self-service solutions, so we’ve never needed salespeople. Recently, however, larger companies asked if we could provide an enterprise version with unique features, and, as we began building it, we recognized that selling a product to enterprise organizations requires a level of attention that only a salesperson can provide. So, we decided to make our first sales hire.

My cluelessness turned out to be an invitation to learn, but reading and asking good questions helped me learn enough about sales to make a good decision.

Talk the talk

Reading about sales processes and team structures had multiple benefits. First, it taught me that I needed a software as a service (SaaS) specialist because selling software subscriptions is different from any other kind of sales. Whereas real estate agents selling a house or ad sales people have a completely different skill set, SaaS sellers must convince someone to continue to purchase their product month after month. 

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