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Why Being Clueless Can Be a Great Thing…

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.

Second, reading taught me lingo like CAC (customer acquisition cost) and LTV (lifetime value), both of which came up in interviews. Vocabulary matters. It would be difficult, for example, to speak intelligently about weightlifting if you can’t name any of the movements.

Once I read enough to imagine the type of candidate I wanted, I had to create a signal that person wouldn’t miss. To create the job ad, I read comparable postings and borrowed phrases I thought were relevant. LinkedIn ads led me to use expressions like:

I hate buzzwords, but I’d rather talk the talk than miss out on outstanding candidates who respond to these key phrases. Finding a strong hire for the first sales role is vital, and the process is as much about selling your company as it is about the interviewee selling himself or herself. You must know what you want before you can go looking for it.

Information versus validation

Asking questions gave me enough information to be creative and enough validation to avoid egregious mistakes.

Before hiring for this position, I was clueless about sales compensation. By interviewing candidates, I covertly learned a lot about salespeople: how they work, how their teams are structured and how they are paid. I didn’t even know how Salesforce worked until a candidate drew me a chart on a whiteboard.  

Interviewing people gave me key insights, as did asking friends. Salespeople work on a base plus commission, I soon learned, but at what percent? To find out, I took a sales-savvy friend out for beers. He told me that salespeople get a range of commissions based on attaining goals they set.

That conversation sparked my idea to base commission on flat numbers instead of percentages. If our new salesperson hit certain sales goals, a predetermined dollar amount is earned. It seemed more motivational than an abstract percentage. I ran the model by my sales friend, and he approved.

That’s the difference between information and validation. Information is passive; you can use it or ignore it. If you seek validation for an idea, you can feel confident if you get approval, but think twice if an expert says, “Don’t do that.”

Taste: the unexpected payoff

Sometimes, entrepreneurs cure cluelessness by outsourcing to an expert. Don’t code? Hire engineers. No marketing experience? Hire marketers. While that seems logical, it’s not always the best approach.

A friend of mine, the owner of a financial consulting company, decided one day to build a SaaS product. He’d never programmed before, but he insisted on learning how. I encouraged him to hire engineers instead and get on with it. He already had a successful business to run, so why make life harder for himself?

To his credit, my friend saw the benefits of immersing himself in the craft that would fuel his future business. By studying programming, he was able to hire the right engineers, manage them and assess the quality of their work.

Recognizing what is good or bad is fundamental to any creative skill. Sommeliers sample wines from hundreds and hundreds of bottles to develop a discerning palate. Programmers sample massive amounts of code, user interfaces and user experiences for the same purpose. My friend didn’t become a world-class programmer, but he did develop taste. Confronting cluelessness head-on earned him that invaluable perception.

The result

Some of my team’s best ideas came from within. For example, our head of marketing came up with a killer, two-part interview question: What is the biggest sale you’ve made, and how did you get that sale? 

If the candidate couldn’t provide details, he or she wasn’t in the running.

I took a long look at people’s experiences. Obviously, what works well in one situation won’t necessarily work in another, but the comparisons give you power to plot your own course and avoid egregious mistakes.

Ultimately, I hired someone who worked at another SaaS company for seven years. That level of experience and rare level of commitment told me that the company wanted to retain him. People who jump ship every year are a red flag — if they were exceptional, the company would make an offer they couldn’t refuse.

If they are exceptional, they probably are unwilling to commit long-term.

The gift of not knowing

Experienced people work under the burden of assumptions, successes, failures and other stories. The clueless don’t suffer from the past. And, while that might shoot them in the foot occasionally, it need not. Cluelessness is a temporary choice.

Bad entrepreneurs either stay away from what they are clueless about or pretend like they know what they are doing. Both approaches never turn out well.

Great entrepreneurs treat obliviousness — and the opportunity to learn — like a precious gift.

So savor cluelessness. It might change your business and your life.

Clueless yet skeptical

When you’re clueless, it’s hard to question advice from people in the know. We may take it for granted and assume that friends and mentors will always offer sound advice. Sometimes, they don’t.

For example, another friend told me they only hire hotshot sellers. For my company, that didn’t make sense. We needed someone who could build a sales organization and shape the product to fit our new market. Top sellers don’t work like that — they tend to spend as much of their time as possible on selling rather than setting the groundwork. They depend on lead lists and team members who get the requirements from prospects. We needed someone with a more diverse skillset and had the experience to not only sell, but build a product.

We ended up hiring somebody with the following plan: He’ll act as the primary (and only) salesperson for six months to develop our model and shape the product according to enterprise feedback. Then, he’ll hire and educate additional people to expand our sales program.

Embracing cluelessness doesn’t mean you throw critical thinking out the window. Stay skeptical — it’s the only way to endure cluelessness without digging your own grave.


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