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Greenville Business Magazine

John Sterling Writes Book on Sales for “Noobs”

Sep 07, 2021 01:47PM ● By David Dykes

By Leigh Savage

If you see a tall busker playing the sax near Liberty Bridge in downtown Greenville, it just may be the man who helped build one of South Carolina’s largest companies - and who literally wrote the book on sales. 

“I love playing music,” says John Sterling, who often walks away with about $20 per night, which he proves by holding up a messy wad of one-dollar bills - last night’s proceeds. 

He doesn’t do it for the money. Datastream Systems Inc., where he was part-owner and global sales manager, sold for $216 million in 2006. 

Since then, Sterling founded Foxfire, which provides warehouse management software, and Sterling Ventures, which invests in startups including and 

He also started writing a book, “Sales for Noobs,” on the second day of lockdown after Covid-19 hit, finishing about 10 months later.

Subtitled “Everything Sales Rookies Need To Know to Crush Quota, Get Promoted, and Kick A$$,” the book was released on Amazon in February, and has achieved steady sales, even becoming a top seller in several categories, including internship and technical project management. 

“A lot of this book - I wish I read it” before starting in sales, he says. “It helps people - where do I fit? It helps people get some lists together to find out. It’s the prework. I just went knocking on doors.”

While he found success, he wants sales neophytes to know that the prework will make success much more likely. 

Taking a shot

Sterling, who grew up in the Upstate, played basketball at the Citadel, where he faced off against the University of North Carolina and a young man named Michael Jordan. 

“He was the third-best player on the team,” Sterling says. “He worked hard on his shooting and did whatever it took to learn how to win.”

While Sterling had skills - and at 6’6”, height - he says he wasn’t NBA material, so he spent a year on a team in Ireland sponsored by Yoplait yogurt. 

Ready for his next move, he heard Silicon Valley was the epicenter of technology, so he drove out there and started knocking on doors. He ended up selling software at Silicon Valley Products. 

He learned a lot during his time in California, but he and his wife Jennifer wanted to be closer to family, so they moved back to Greenville, where Sterling took a job at Michelin as a third-shift tire loader while looking for work during the day. 

“I was determined that I was going to be a successful entrepreneur,” he says. 

Then he met Larry Blackwell, Datastream CEO, who had a Ph.D. and a great product - asset management software. The company was early to the space as more companies were moving from paper to digital systems. 

“I started with Larry in what is now the Greenville Heart Association building, and my office was the conference room,” he says. He became an equity owner.

Datastream turned out to be what Sterling calls a “unicorn company.” After selling to Infor for $216 million, it was bought by Koch Industries and recently sold to Hexagon AB, a Swedish industrial technology firm, in a deal valued at $2.75 billion.

Sterling was responsible for hiring hundreds of salespeople between 1986 and 2006 as the company expanded from four employees to more than 1,000. The company went public in 1996.

He learned a variety of lessons during this period of explosive growth, which he shares in the book. A few takeaways for salespeople - noobs and otherwise - include:

Think about the basics. Where do you want to live, and what would you like to sell? He says selling something related to a passion, such as music or basketball, can help people stay motivated in a field they love. 

Sales isn’t just for outgoing, gregarious people. “A shy, reserved person can be great at sales,” he says, since the key is listening. He likens it to a doctor, listening first to diagnose. 

Don’t socialize too much with clients or prospective clients, especially where alcohol is involved. “It’s like drinking with your doctor,” he says. “You want to be someone who can help them and solve their problems.”

Put in the legwork for high-value customers. Put in the research to find them, and then continue reaching out to them in a “slow drip. A slow campaign to get to know them.”

Design your day. “There is a difference between goal and process,” he says. “The goal might be two sales, but it might as well be ‘I want a pony.’” Instead, he suggests being more specific: “I’m going to call six people before lunch and six people after lunch.”

In addition to the book, he built a website,, to help people launch their careers. It will include free videos, podcasts and a weekly Zoom class that will help people find their perfect job. 

“We’ll have coaching for business owners who want to have a better handle on how to scale up a team - I have done some of that,” he says. 

He also oversees, designed to “take your technology sales team from noobs to pros.”

As for Sterling’s day, he still gets up at 5 a.m and works on business and self-development projects. He starts his calls early, around 7 a.m., and then exercises at 10 a.m. His afternoon is more flexible, but practically every night, he’s downtown with sax in hand. 

He typically plays jazz, and in addition to dollar bills, he is sometimes offered people’s leftovers from dinner. He says no thanks, but loves to engage with the folks who stop to listen. 

It’s that interest in connecting with people that propelled him to success in sales and led him to write a book to help newbies learn more about it. 

“This book is just meant to help people,” he says. “There are a lot of sales books, but I had this unique experience working with young sales people right out of college. There is a benefit to planning and getting into the right spot.”