When Start-Ups Sell to Enterprise: Mistake #1

When I started selling Brand Amper, I expected that enterprises had never seen anything like our amazing new technology. That was the cause for a lot of bad sales calls, and I should have known better: the buyers at these enterprises had long been using their self-improvement budgets to go to the very same conferences I and other innovators had been speaking at—places where this idea and similar ones took shape; their logos had been drawing pitches from that same gaggle of competitors and innovators for years; incumbent vendors had been long since promising that a version of pretty much the same idea was on their product roadmap... somewhere. Doh! I should've known this. I literally knew the buyers and competitors by name. So why did I make that mistake?

Life inside a start-up makes the reality within enterprise companies hard to imagine. At a start-up, communication and decision making is done so quickly, technical superiority is so prized, and the true north of "be 10x better" is so ruthlessly hammered home, that it's next to impossible to fathom how a company with such incredible resources as an enterprise could be so slow to adopt such an obviously superior way of doing business. I knew this, yet I still fell prey to it, and as a result, I did my fair share of bad pitching.

Through constant analysis of our sales process (and frank discussions with prospects), we were able to remind ourselves of the life of a buyer. We learned quickly that the barrier to a sale almost never had anything to do with our solution, and everything to do with how decisions got made inside the enterprise.

As I adapted to what we learned (about budgeting, politics, approvals, change management, risk mitigation, strategic prioritization, etc.), I found myself using my deck less and less on sales calls. Instead, I'd start with a demo. Any question that could be answered by literally showing the tool, I'd answer by literally showing the tool. Then I'd engage in a discussion. Price was a part of it, as was the question, "Why would you buy it... and why wouldn't you?" If I need my deck after that, it was usually to answer a follow-up question, so rather than go through all 75 of my slides, I could jump to the relevant slide(s) and skip the rest. I would even leave the nav bar up in Keynote as I jumped around—no presentation mode. It may not have been quite as polished this way, but I found that didn't matter. They were more than willing to forgive that as long as I was focusing on their questions rather than my presentation.

True, start ups live and breathe their new thing, while the enterprises they sell to live and breathe the tried-and-true thing. But what's not true is the mythology within start-ups that enterprises are out of touch. The reality is that they are full of smart people who have "been there"... even if they haven't yet "done that."

Calibrating on this reality can put a tremendous amount of accelerant on a start-up's sales process. It certainly did for ours! And while there were plenty of other problems I learned to overcome—including underestimating time to close and mis-pricing—this was the one that, when I started to address it, unlocked all the others.