He began what would become a storied sales career in the mid-’70s, selling bumper stickers while attending Christ Church Episcopal School. College summers were spent peddling umbrellas and beach chairs through 10-hour shifts, seven days a week as a Myrtle Beach lifeguard.
Even then, John Sterling says, the sales bug still didn’t bite.
He turned down the ultimate pitchman, Mike Krzyzewski, the legendary basketball coach who recruited him for Duke. Instead, Sterling attended The Citadel, where he also realized he wasn’t cut out to be a doctor or engineer.
Nearly 40 years later, the Greenville native, 59, is widely known for his role in Datastream’s startup in 1986, becoming its global sales manager and seeing the company sell to Infor for $216 million in 2006. He has also written the actual book on sales.
Released in April, the 176-page business-help manual is titled “Sales for Noobs: Everything Sales Rookies Need to Know to Crush Quota, Get Promoted, and Kick A$$.”
It’s not that he was reluctant to go straight into sales after graduating from The Citadel. Rather, he says he wasn’t ready to make such decisions.
“I didn’t take the time to really, really think it through when I was in school. It’s because you’re kind of scared of the answer. You know, you’re kind of like, ‘I don’t want to deal with it right now. I’ll deal with, y’know, my job later.’ That’s exactly why I wrote the book — because my brain was not evolved enough.”
He put that off, too. After earning his bachelor’s degree in 1983, he played a season of professional hoops as a forward for a Yoplait-sponsored team in Dublin, Ireland.
‘Call people and sell them something’
Once he got all that out of his system, he drove out to Palo Alto, California, and “started knocking on doors.” This was the mid-’80s, the dawn of the tech explosion.
Nolan Bushnell, who founded Atari, was one of his mentors.
“‘Here’s your office, here’s your phone, here’s your list. Call people and sell them something,’” he recalls Bushnell telling him. “And, y’know, I just liked it, I enjoyed talking to people.”
He then returned to Greenville, where he finally tapped into what he had known all along — that he wanted to be an entrepreneur.
More recently, he took some open time during the pandemic to write “Noobs,” a play on Citadel cadets’ first year as “knobs” and a sales term for a newbie.
“I wrote the book because people do things for dumb reasons. Very often, they don’t have enough information, so the book is meant to try to help get them thinking about who they are,” he says during a Zoom from his condo in downtown Greenville.
As he writes, “Unlike every other sales book, it tells you explicitly what not to do.”
Amazon, meanwhile, describes the tome as “the mentor they need to skip the bullsh*t [sic] and stop chasing prospects.”
A serial entrepreneur who has started or invested in at least 10 tech companies — so far — Sterling has mentored hundreds of salespeople. He says 65 of them have gone on to become C-suiters in marquee IT companies or venture capital firms.
The ‘Datastream mafia’
Today, they’re collectively known as the “Datastream mafia.”
“They help each other. You can call somebody else in the mafia, and say, ‘Hey, I need someone to do this or that for me,’” he says. “It’s a nice community.”
Alex Estevez is among those. He started with Datastream in 1997 and served as president and CFO from 2005 to 2006. Now he is an Atlanta-based partner with Accel, a global venture capital firm that has financed the likes of Facebook, Dropbox, Spotify and Venmo, among others.
“John has a gift of really understanding what a customer is saying, sometimes before they even say it,” he says.
That echoes Sterling’s own definition of sales.
“Finding a need and filling it,” Sterling says, chuckling. “That’s really strong, that’s tight.”
Busking under the bridge
He likes his jazz tight, too.
Every night, he ventures from the condo he shares with his wife of 35 years, Jennifer. Under the bridge at Reedy River Falls, he pulls out his Heritage tenor saxophone and plays blues, standards and his personal favorite, Dexter Gordon, one of bebop’s early influencers.
Sterling says he earns money as a busker, too.
Asked if he’s any good, he replies: “Damn right.”
And when he’s not busy with his latest enterprise, Foxfire Software, which provides warehouse-management solutions, he takes his show on the road. With classes and consulting, as with his book, he aims to instill that same fervor in today’s sales noobs.
Estevez calls Sterling a sterling example.
“He has the leadership skills to help others develop these insights in a way that has positively impacted countless business and sales leaders throughout our region.”
Then, with a Sterling-esque sales pitch, he concludes, “I couldn’t be happier for his new book, his positive impact on others and his overall success.”
Nuggets from ‘Noobs’
“Sales is one of the most interesting and mysterious games in the world.”
“Meteorologists have better luck at their job, and weather forecasting is fortune-telling for people in suits. As a sales noob, you’re a fish in a shark tank. Your job probably feels like a constant battle to defend your product against customer objections, competitor attacks and demands for special discounts. It’s exhausting. Even if you say and do all the things you were taught, you may still get eaten for lunch by three evil words: ‘Not right now.’”
“Unlike every other sales book, it tells you explicitly what not to do.
- How not to prospect.
- What not to say during a call.
- Which sales jobs and promotions to never accept.
- How not to hire and train salespeople when you’re a manager.
By showing you what not to do, this book can help new salespeople avoid flawed advice from well-meaning sales gurus. … What derails a sale — and eventually a salesperson’s career — is not that they forget to do what they were trained to do. It’s that they do what they should never do because nobody ever told them not to.”