This continues our series of front-line sales interviews, featuring quota-carrying sales reps as well as their managers and leaders (see previous interviews here and here). In this interview, Focus VP of Sales & Marketing Craig Rosenberg (whose alter-ego is The Funnelholic) talks about what it takes to survive in a start-up sales environment. It’s not always pretty.

What’s the hardest thing about your selling environment right now?
First of all, no matter the environment, selling is really hard work. You work your butt off to get to a few customers who need what you’re selling. But that job is even more difficult in a start-up environment. At a big company, you miss your number and that sucks for you but the lights stay on and everyone will live to see another day. At a start-up, you miss your number and people may lose their jobs or worse.

One the best pieces of advice I ever got was from one of my mentors who was an ex-VP of Sales from IBM. He told me never to hire a new sales rep from a big, successful company, as they have no idea how hard it can be to sell without the training wheels. Not only will most people take a call from IBM (vs. your no-name company), but big companies have more resources to help the sales team – sales engineers, marketing, legal, etc.

At a start-up, the Donald Rumsfeld rule applies: “You go to war with the army you have—not the army you might want or wish to have at a later time.”

Net-net, start-up selling means you have less resources and you HAVE to hit your number. Sound fun? It is for guys like me but it is not for the weak at heart.

How has sales changed recently, and how do you take advantage of that?
At a start-up, you have to be an evangelist, too. You have to take the time to educate your prospect on something they may not yet understand, and help them put that into the context of their business and their own little world within it. It’s still brute force and lots of sweat – tons of meetings, losing lots of deals, getting rejected a lot, to get to the wins that help you start to grow the business.

It’s not for everybody.

In a nascent market, does sales have a role in helping define the market opportunity and the go-to-market strategy?

Absolutely. In a start-up, the most efficient way to get market intelligence and market traction at the same time is to just start selling. You’re going to be wrong a lot early on. For example, we did a ton of meetings before we realized our buyer personas were wrong, but we fixed them in real time. We made significant progress, quickly. Now, we are far more efficient at identifying companies we can help, and the individuals within those businesses who need us.

There’s a saying that applies particularly well to start-up sales – “you don’t always want to know how the sausage is made.” Can you relate?
One of the biggest advantages we have is that our CEO and our investors know how hard this is. We’re really focused on having as many conversations as possible. We have purposely not burdened ourselves with restrictive lead definitions. That may come later, but right now we’re trying to learn what works, what sells, and whether the market want our product. It’s machete in the jungle for sure.

I talk to a lot of sales executives, particularly at younger companies, who also are in the sausage-making business right now. What worked in sales 20 years ago isn’t as relevant today. There isn’t a standard that works in every environment, every market, with every buyer. There’s some solace in knowing that others are struggling with this too. But at the end of the day, you still have to hit your number.

How important is it for a start-up to have a head of sales that understands the start-up sales environment?
It’s critical. There are plenty of highly-successful, serial sales executives who simply cannot execute in a start-up. There are exceptions, but in general their vision of how it should work doesn’t jive with reality. There are plenty of good start-ups that die because they believed in someone who couldn’t do it, and stuck with him or her until it was too late.

  • Matt, Craig:  Thanks for a great discussion.  The start up environment has so many unique challenges for sales–both the type of people that are successful, the nimbleness, and the sheer ability to get a customer to invest in a new thing!  Great interview–Craig is a real master in this environment!