There are as many reasons why dealers engaging in managed IT services succeed as there are reasons why they fail. One reason for failure is sales reps who have not bought into prospecting for IT opportunities because, well, because there’s nothing in it for them. They do the work; the IT specialist gets the glory and the compensation.
Compensation aside, and that’s a big aside, let’s focus for a moment on the sales skills of the average sales rep. Sure, they can sell traditional imaging equipment and services like MPS, but when it comes to IT, they’re sometimes befuddled, yet they are expected to find opportunities. As more companies realize this, wouldn’t it be nice if there were a sales training program to provide these reps with the skills necessary to sell IT services or at least identify opportunities?
Well, there is. The Kingston Training Group recently announced a strategic partnership with ConnectWise to provide this training. ConnectWise contributes up to 50% of eligible Kingston Training Group investments from ConnectWise Market Funds, reducing training costs for ConnectWise partners and, as stated in the press announcement, “accelerating their path to enhanced competency and business growth.”
The IT Factor in Sales Training
The curriculum covers service delivery, operations management, cybersecurity, and sales enablement, ensuring the dealership’s sales teams possess the technical knowledge, certifications, and strategic insights to excel. According to Kate Kingston, founder of Kingston Training Group, it’s about creating more net new opportunities and converting current imaging customers to managed IT. Kingston contends that after four months of training, a dealership can change the culture to be more IT-focused via the right talk tracks, time management, calendarization, and accountability.
Kingston worked closely with the IT team at Novatech, an office technology dealership that rebranded into a national IT service management company, to put this program together. “Having that education in my arsenal ensures a full understanding of what happens behind the scenes, which allows that business swagger into the pitch itself when we’re trying to schedule more meetings,” said Kingston.
Training will not be limited to general line sales reps but will also include subject-matter experts, territory reps, and major-account reps, basically everybody involved in driving a dealership’s IT initiative. “The subject-matter expertise role needs to support the down-the-street rep and drive their own net new 10 to 15 to 20% of the time,” observed Kingston. She is also training the managed services reps for Toshiba across the country, adding further credibility to the training.
Been There, Done That
This is not Kingston Training Group’s first rodeo in the managed IT segment. “What’s unique about me is that I never sold the boxes for a living,” explained Kingston, who has been exclusively focused on training the imaging channel for over 25 years. “I was never box mentality. I’ve been discussing how IT impacts your compliance, security, efficiency, and profitability goals from the get-go. I’ve watched that evolution and tried to stay in front of it. We always focus on what is next to bring value.”
IT Due Diligence
Doing her due diligence and monitoring the space for many years through her training and interactions with dealers, Kingston has seen it all, including those who have been unsuccessful in the IT space. And she’s got some opinions as to why. “I don’t want to mention names, but I’ve had a couple not compensating the territory reps effectively for bringing that opportunity into the fold,” said Kingston. “That’s a big mistake.”
She explained that a sales rep’s job is to sell all the solutions the dealership offers to run a customer’s company more effectively. “You have to let your subject-matter experts in,” she said. “That’s the biggest problem. We have reps saying, ‘I don’t want them to screw up the account or mess up the account.’ Well, it’s not your account; it’s the company’s.”
However, the onus of identifying opportunities isn’t the sole responsibility of the sales rep. The subject-matter expert needs to step up too. “One of the things I tell experts, including in managed IT, is to change the mindset of saying, ‘Are there any partnership reviews you think I might be right for?’” noted Kingston. The better question for subject-matter experts to ask sales reps at the beginning of the month is, what three partnership reviews are you bringing me in on this month? Or ask, which is the best prospect where we make sense in a net new for a ‘four-legged’ meeting or a partnership review?
Kingston said a dealership with 10 reps should have 30 current customer meetings a month, ideally for managed IT. “That’s almost all you would have to do,” she emphasized. “You turn those into an assessment or a paid assessment. It creates a commitment from the customer, which is harder to get, but a better commitment, and then the close, so you could easily see how that would increase the revenue folks are looking for from their managed IT solution suite.”
Talking the Talk
Kingston Training Group’s curriculum is designed to be understood by whoever is trained in the dealer organization. “From the beginning, I thought about talking in the customer’s language, French, to the Frenchman, if you will, so they understand you better,” noted Kingston. “Because we’ve done it before, we can be hyper-focused on a solution, a vertical, an executive, or the company.” She also claims to be the only training organization that has verticalized every selling solution from production print to cybersecurity, mailing solutions, and managed IT.
For example, when selling to a law firm, the training might focus on compliance matters that could be accomplished through managed IT. For an accounting firm, the training might center on securely archiving information. “That’s where we get into a redundancy plan and in the cloud and security,” Kingston said. “Compliance and security are big pieces of this puzzle in today’s climate. Since dealers are service providers, we must consider the company as a whole and that securing their data is a priority.”
The cliché “you get what you pay for” can certainly be applied to sales training. “If Kingston Training Group’s training were free, everyone would do it,” said Kingston. “If our training costs the dealer 50% because of market funds, it makes it easier for the dealership to jump in.”
However, she offered a caveat. “You still have to dedicate time and energy and be passionate about prospecting because it’s not a light endeavor to come into a dealership to say, we’re going to take that rock up the mountain, not just hold it there. You’re asking folks to work a little more for a lot more. Some sales teams want to flip their base and not add to it. That’s not where I fit in. I need people hungry for more and dealerships committed to more, just like ConnectWise is for dealers.”
IT Sales Optimism
Several dealerships have already signed up for the training. “We are going to be tracking these results for ConnectWise and the dealer community, and it’ll be fun to talk about it next year and see the increases in a dealership in not only net new business but also bringing some of their current customers along,” observed Kingston. “Everybody has high revenue goals for 2025, and this is an easy way to get it. We guarantee at least a 50% increase in meetings, including managed IT meetings, or our training is free.”
There’s also a benefit to ConnectWise besides more successful dealer partners—the potential to add more dealer partners. “Whenever I find a dealer that’s not using ConnectWise, I tell ConnectWise about it, and I connect them because it’s the best program I’ve seen thus far,” Kingston said. In mid-2026, “I’ll have 10 or 15 dealers with concrete numbers from start to finish,” she said. “And I’m going to be helping as many dealers as my calendar will permit because we’re going to guarantee the results.”
