The New Hardest Job in Sales – Reflections from Dreamforce Expo 2015

hardest job in sales dreamforce 2015

“Welcome to the world’s largest cloud ecosystem. At the Cloud Expos, you’ll find unlimited ways to transform your business…So take a deep breath and get ready to learn, learn, and learn some more.” These were the words that graced the opening page of the Dreamforce Cloud Expos pamphlet.

Benioff and company have thought of just about everything – meals, transportation, accommodations – and this year, there was even the Dreamboat – a luxury cruise ship to accommodate 1,100 of the now 150,000 strong that came to San Francisco this year. But if you ask me, they missed the couple of Xanax that should have come with this pamphlet!

Last year, I suggested that the Expo was the Modern Roman Forum – a place where reps engaged in the purest kind of hand-to-hand combat. 300+ cloud vendors competing beside one another. With all of this choice, how are sales enablement leaders supposed to determine where to invest?

Welcome to the new hardest job in sales: being a buyer in this new Golden Age of Sales Enablement. We can solve problems today that we could not have dreamed of just five years ago. Your mission, should you choose to accept it, is to figure out which ones you should actually solve.

While walking the floor though, there was one overwhelming theme that stood out. Each vendor held the promise of selling nirvana – something better, faster, or what we at CommercialTribe call efficiency. is the new posterchild, leading the analytics revolution. Jim Steele, Founder and CEO, delivered a session on Moneyball for Sales comparing his company to Michael Lewis’ famous bestseller on how the Oakland A’s used data to revolutionize baseball.

Whether it’s lead management, pipeline management, email tracking, proposal and document management, or now analytics, all of these tools hold the promise of a more efficient sales team. But there was still something that felt missing. Not a single vendor among the hundreds could influence the moment of truth – when a rep is in front of a prospect or customer and decisions are ultimately made. It’s what the CommercialTribe team calls efficacy.

There were plenty of decisions to be made every second on the Expo floor. Box vs. Dropbox, Tableau vs. Domo, Caladys vs. Xactly, ToutApp vs. Yesware, SalesLoft vs. InsideSales…the list goes on.

So I journeyed through the Expo floor asking a series of questions:

  • What do you do?
  • What problem are you solving?
  • Who do you compete with?
  • Why should I invest with you vs. something else?

A few select reps were up to the task, but sadly, many were not. When you stop and think about the investment companies were making in booths, travel, and marketing, the idea that reps are not locked down to answer these types of simple questions…well, it feels like doing all the hard work to make it to the Super Bowl, but electing not to practice before the big game.

There was one rep from one very high-profile company (which will remain nameless to protect the innocent) that got so flustered by these questions that she looked hopelessly to a colleague, who couldn’t come to her rescue in the chaos of the Expo floor.

“When’d you start?” I asked.

“5 months ago.” She replied.

I wish I could have handed her my complimentary Xanax…

‘Till next year, Dreamforce!

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