Where Will Your Sales Career Be in 20 Years?

Twenty-one years ago, I was in my fourth year as an account executive with a big, relentlessly negative sales culture. In the previous year, I was lucky enough to have finished first in new business sales out of around thirty in the region, but I’d never have known it. First place still meant achieving just 70% of my target, so everyone was equally treated as a failure.

On our performance reviews, each rep was ranked from top to bottom. If you finished in the top third, there was an "X" on your feedback form ("X out of 30"). If you finished in the bottom two-thirds, there was a number showing where you ranked. I guess the philosophy was to not provide evidence of success, where unachievable quotas and an "X" on your performance report meant you would have no proof for getting your next job.

Things changed in 1997 when I joined SAP North America. I was assigned a workspace in a four-cube squared-off area in an office located in Westchester, Illinois with three other sellers. That area would soon become known as the "Romper Room."

The four of us in this area consistently overperformed, and also consistently made "fun" a priority. There were no ping pong tables in the offices back then, so we brought in our own Nerf hoops for free throw shooting competitions along with an occasional slam dunk contest, as well as a 1-iron golf club for Nerf golf down the hallway.

We learned early in our careers that we performed better when we weren’t constantly looking over our shoulders, and when we loved who we worked for and who we worked with. We all knew that to succeed, we needed to bring energy, dedication, a thirst for learning, and positivity to the office every day. We focused on trust and transparency with our clients. We were modest. We were never heavy handed. We never stepped on people to get ahead.

I’d like to think we helped usher in a new way of thinking about sales culture. The four of us brought this way of thinking to the teams we led, who brought it to their teams, and so on. Boiler room atmospheres and Glengarry Glen Ross type contests were things of the past. Today, pop-a-shots and video games are as much a part of the modern day office furniture as are desks and phones.

Last Friday, the four of us from the Romper Room got together for lunch. It was our first time together in 20 years, and none of us could have imagined what we’d each be doing today:

Todd Caponi.png
  • DJ Paoni (white shirt) is now the President of SAP North America.
  • Steve Szymanski (far right) is what I would call “semi retired.” His success has given him the ultimate flexibility.

  • John Savage (far left) is now a Vice President at SAP North America, overseeing a team of VPs.

  • And I (dorky guy next to John) just finished almost four years as the CRO of Chicago’s fast growing PowerReviews, and am now writing the book, The Transparency Sale, which will be out in the fall.

It’s amazing how each of us from the Romper Room did things the right way, and proved that approach wins. The sky's the limit when you do things the right way, too.

The right way is having a constant thirst for learning versus being a know-it-all. It’s being a great teammate versus winner-takes-all. It’s staying positive versus misery-loves-company. It’s practicing empathy versus aggressive script execution. It’s being genuinely modest versus being a braggart. Then, in 2038, you’ll be having lunch with your former co-workers who became lifelong friends, dumbfounded by how well you all did.

Todd Caponi | Author, The Transparency Sale and Principal, Sales Melon

Todd Caponi