There are no two words in the English language more harmful than ‘good job.’
—Terence Fletcher, Whiplash
The quote is delivered brilliantly by actor J.K. Simmons, playing an instructor at a music conservatory who is hell-bent on cultivating Charlie Parker-level greatness in one of his students. While the theme of never settling for a lesser version of one’s self is admirable, Fletcher takes it to an insane degree that is emotionally crippling. The main problem for Fletcher is that he knows what great looks (sounds) like, and constantly hounds his students in pursuit of perfection, and will not tolerate less.
Derek Shebby knows what good looks like from the point of view of a sales coach and mentor to the office technology dealer space. The president of Modern Sales Training has guided sales reps who have eclipsed $2 million in annual sales, and has reset expectations for account executives who feel $50,000 is a “good job.” But while Shebby has never been compelled to hurl a laptop computer at one of his students to get their attention (as Fletcher did with musical instruments), he can spot instances where reps have become comfortable with mediocrity. He can also tell which young sales hotshots are believing the hype they’ve been feeding themselves. Frankly, it was once him.
The year was 2003, and Shebby—fresh out of San Diego State University—had taken a sales position with Mister Copy (MRC), a Xerox agency based in America’s Finest City. At 23 years old, Shebby was brash and more than a little cocky, unafraid to tell fellow reps that he would soon be “crushing” their sales numbers. But something happened during Shebby’s first 90 days with the company that would eventually mold him into a sales guru to the industry. Or didn’t happen, depending on one’s viewpoint. He didn’t sell anything.
Wakeup Call
One day, Shebby’s boss, John Taumoepeau, called him into his office and slid a piece of paper in front of him. It was a written warning that if Shebby didn’t sell anything with a month, he would be terminated. Shebby was asked to sign it.
“Here I thought I was going to be this amazing salesperson,” said Shebby, a 2023 ENX Magazine Difference Maker. “Now, I was on the verge of being let go. I couldn’t imagine telling my family and friends that I had been fired for a lack of performance. Up to that point, I hadn’t been coachable, because I thought I knew better than anyone else. I had too much ego.”
Taumoepeau then asked an important question: Did Shebby want to work at MRC. Shebby said yes, so his boss and the other sales managers vowed to work with him and improve his game. That entailed coming in at 5:30 in the morning, before the start of the business day, to role play and develop the skills he needed to be successful. A couple of weeks later, Shebby sold a $3,000 copier to a local animal hospital. Properly admonished, he pivoted to discover the best tactics and approach to earn more than a “good job” pat on the back.
Shebby would go on to have a successful 17-year career with MRC, which grew to the $200 million plateau after being acquired by Xerox’s Global Imaging Systems. His roles continued to evolve, from top sales rep to sales manager and then vice president of sales. In that final position, he helped develop many of the firm’s vice presidents and cultivated sales reps fresh out of college.
Building Steam
Along the way, Shebby created a number of B2B outside sales courses under the Modern Sales Training flag. He posted them onto a skill-building site called udemy.com, and it soon became the number-one course for B2B sales. In 2020, he could sense the Global platform was shifting, and decided to part ways with MRC. But he made a multitude of connections in the general business world, including John Deere of farming equipment fame, where he worked with the corporation’s largest dealership in Fargo, North Dakota (the company remains a client). That opened the door to partnerships with other manufacturers in the agriculture space.
Modern Sales Training gained greater clarity in 2021, as Shebby was contracted by a dealership in Fresno, California, that needed help. He had been referred to the dealer by that company’s manufacturer rep, who had been trained by Shebby back in the day. In short order, Shebby assisted the dealer in “selling MPS fast,” including a $6,000/month contract with a net-new client. That became Shebby’s calling card, as he signed on with the BTA to do a webinar on the subject. That led to a MPS workshop for the Select Dealers Group peer organization, and eventual sponsorship by Clover Imaging Group.
In a matter of two years, Shebby’s platform had “grown like wildfire.” The Modern Sales Training kingdom now consists of a 12-week sales bootcamp (he conducts eight per week), a coaching curriculum for sales leaders and managers, and the Outliers Group for high-performing reps, in addition to the MPS training.
“I like to win,” Shebby said. “The real test of my ability is, can I get other people to be as good as me and produce exceptional results. These companies are investing in me, and the sales reps are investing in their own careers. I expect them to have great results. None of [the training] is based upon theory, just facts. Seeing them have positive results is exciting.”
The success stories embolden Shebby to push forward to greater heights. One East Coast dealer that was recently acquired improved its price tag by registering more than 60% net-new business, which was attributed to his training program. Shebby believes the content he delivers is easily digestible, and more importantly, highly actionable.
The courses are also straightforward. “I cut away the fluff,” he said.
Keep it Simple
While Shebby has gained perspective from a number of resources, it’s impossible to deny the impact Taumoepeau had on his career, not to mention his line of thinking. A former linebacker at Oregon, Taumoepeau was adept at following the rules for sales success, so much so that Shebby named one of his podcasts “Following the Directions to Sales Success” in his honor.
“John was taught a way to do things, and he mastered it,” Shebby noted. “He didn’t try to make it his own. He just followed the rules and did it better than anyone else.”
Modern Sales Training continues to set new sales standards in each successive year. He formed the Outliers Group in 2022 in order to harness the magic that the highest-performing reps have wielded. It currently has 40 members and Shebby’s goal is to reach 100 and continue to add stalwarts from all industries. It’s not a velvet rope society; Outliers, like all of the programs in Shebby’s catalog, needs to demonstrate value.
“Outliers make ridiculously more money, but they’re also doing things differently,” he said. “I hope it continues to grow, because it’s where I get to focus on whatever people need help with, kind of like an outsourced sales leader. It’s challenging for me, because I want everyone to feel, every single week, that they’re getting so much value that they want to continue to be in it.”
Seeking Perfection
He is constantly setting goals. In fact, every 12 weeks, Shebby creates a new list of objectives, Inspired by Brian P. Moran’s “The 12 Week Year.” He frames the lists and hangs them on the wall by his desk. Shebby seems obsessed with learning from the very best and hunts for mentors whenever possible. When his son joined a chess club, Shebby began studying the strategy of professionals such as Magnus Carlsen of Norway, and played for an hour each day.
“I can now crush any amateur,” he said with a laugh.
Shebby and his wife, Jessica, have been married for 13 years and have three sons—Branson (9), Bodin (7) and Brendan (2). The boys are into club soccer and get individualized training. The Shebbys are foodies and wine connoisseurs who enjoy traveling, with Italy and Maui among their favorite haunts.
Reading is another passion for Shebby, particularly fantasy novels. “I love stories that allow your mind to escape and be in a different world,’ he added.
