Trueline Spotlight: Coaching ‘em up

Reading Time: 4 minutes

Phil Jackson had Red Holzman. Bill Belichick had Bill Parcells. And Boston Celtics coach Ime Udoka had Gregg Popovich. Almost every great coach in sports history can count the lessons learned from observing a former coach.

The same can be said for Jason Williams, co-coach of Trueline’s sales development team. In his role leading the group of 14 who make outbound cold calls to the people profiled in Trueline’s magazines, Jason often remembers his basketball coaches from eighth grade through high school.

“My coach in high school always encouraged his players to ask questions, and that’s what I do with the sales development coordinators,” Jason says. “If I didn’t ask a question before a drill and then got something wrong, it was my fault, and we all ran sprints. It was burned into me to ask questions, even if it’s a potentially dumb one.”

Jason Williams in his F100 truck

The SDC position isn’t for everybody, Jason says. When he started at Trueline in July 2020 as an assistant content coordinator—a position that morphed into the current SDC role—he had some challenging days. When making cold calls, there’s always a chance of the person on the other line either not answering or hanging up on you, he says.

“During one of my first days, I made 120 calls and not one person picked up the phone,” Jason recalls. “It was a rough day, but it was a learning experience, and it’s something I tell the SDCs about often.”

Selling Yourself

Jason grew up in a town in Western Massachusetts that was so small it didn’t even have its own gas station. What Northfield lacked in amenities it made up for with small-town charm, he says.

He earned a degree in communications from Salem State University, where he had several stories published in the independent Salem State Log. While searching for an internship as part of his graduation requirements, Jason came across a local meadery, 1634 Meadery in Ipswich, Massachusetts. He asked the owner if he needed an intern and started working a few weeks later.

Jason Williams scooting around on his grandfather's old moped

Following graduation, Jason spent several years selling craft beer and mead, but he never found himself passionate about the work. He says he liked the meadery and the people, and the product was amazing. But at the end of the day, working in a small craft alcohol producer means mostly cleaning tanks in a damp garage. That’s when he moved on to selling beer at another company.

“It certainly helps to know your stuff, but I wasn’t the most knowledgeable. I just really enjoyed the product,” Jason says. “But despite being 6-foot-2 with a deep voice, I’m easy to talk to and I enjoyed the beer, so I was able to expand my sales area and move the products into new markets.”

Whether he was selling craft beer, honey wine or the potential of a premium spot in a Trueline journal, Jason agrees with what David Spade’s character says to Chris Farley in “Tommy Boy”: “In a way, these people are buying you, not just brake pads.”

It’s words of wisdom and advice like this that Jason passes along to his SDC team. And so far, everyone seems to have gotten the message.

Finding his True(line) Calling

Jason’s current position didn’t exist when he joined Trueline, so he started making calls on behalf of Blueprint magazine which features executives in the construction industry. He says it became apparent quickly that if he wasn’t having fun, the job wasn’t going to be a pleasant experience.

“You’re expected to make a lot of calls, so you need to have personality and need to have fun, or you’ll get turned down very quickly,” Jason says.

He knew he didn’t want to stay in a sales position for the rest of his career, so as soon as the SDC department took shape, he went to former Trueliner Ian Nichols.

“I said the company was going to need someone to manage that team, and I told him it was going to be me,” Jason says.

More than a year into the job, and with minimal management experience until his first day in his current role, Jason says he has found his stride.

“I know when to press the issue and push my team, and I also know when to step back and let some things work themselves out,” Jason says. “I like to think that I’m a pretty good manager.”

Jason Williams and his nephew

Currently working from home in Massachusetts, Jason is planning to take his management talents to Maine this summer with his girlfriend, Shauna. She works remotely for a company based in Maine that may require in-office work again soon. Right now, the duo is in the pre-qualification part of the mortgage process.

“If I can be personable and charming and funny like I am at work and with friends and family, maybe we can get a better deal on a house,” Jason says with a laugh.

Bonus Facts on Jason Williams:

Did you know? During the pandemic, Jason got into leathercrafting, and he’s made leather briefcases and a Viking helmet. His face and name are on a bottle of mead at 1634 Meadery. He shares a birthday, September 11, with Ludacris, Taraji B. Henson and Harry Connick, Jr.

Who’d play you? Chris Evans

Bucket list: Bike the East Coast Greenway, which stretches 3,000 miles from northern Maine to the Florida Keys.

Greatest achievement so far: Being a really good friend to a lot of people and not being a jerk.