There’s an interesting confluence of products, technology and people that’s taking place at Usherwood Office Technology. This year, the company is celebrating its 50th anniversary of serving the needs of New York state clients from its Syracuse headquarters as well as the northeast/New England corridor courtesy of its 18 additional locations. Consider that of the aforementioned trio of value propositions, there’s but one constant—its people—that will guide the fortunes of the company for the next 50 years.
Products come and go; after all, when the Usherwood family initially hung its shingle, the hottest office needs were cash registers, typewriters and calculators. Then came the MFPs, followed by security/access products, telephony and video conferencing. CEO Lou Usherwood isn’t the Pollyanna type; he’s been around long enough to know that there are elements in the company’s current portfolio that will, sooner or later, follow cash registers and calculators out the door. He’s seen that movie before, so to speak, and knows how it ends. That’s why people will be the wild card propelling the dealer’s success.
Replacing team members with AI isn’t happening. To take away the human element is to remove many of the qualities that give Usherwood Office Technology its personality and competitive edge. Its raison d’etre is demonstrating a care for customers, which is something only a developed and meaningful corporate culture can accomplish.
“At the heart of what we do is no matter what, we need to drop everything to help the client,” Lou Usherwood said. “Our people make the difference. They’re the ones who answer the phone calls within the first three rings. That’s the kind of culture people like and the reason they want to work for us. They’ve all either worked for companies that didn’t take care of clients or, as clients themselves, they’ve felt like a business didn’t really care for them.”
Technology has been kind to the dealership, particularly with the growth of managed IT and its increasing influence within cybersecurity circles. Chief Technology Officer Charlie Usherwood—Lou’s older brother—immersed himself in the computer movement from the beginning, cutting his teeth on the Microsoft Disk Operating System and remaining on the front line of learning. And now, as the dealer seeks to eclipse the $300,000 mark in revenue per employee, AI is positioning itself to be an efficiency catalyst in achieving that end.
Fine Line
As a family-owned company, there’s an added degree of difficulty for the Usherwoods: leveraging the best elements of a family-owned business with shared values and focus while avoiding the negative connotations of lacking resources/firepower associated with mom-and-pop shops. The dealer has its share of heavy hitters; the brothers are fortified by Lou’s three daughters—Lauren, Lindsay and Leslie—who play vital roles in shaping the company culturally and from an Xs and Os strategy standpoint.
Charlie’s extensive tech background has been invaluable. Having that historical perspective isn’t as much about the machinations of technology as it is the cadence of its emergence and anticipating shifts/sunsets before they become apparent to most. He remembers how contemporaries clung tightly to the belief that the typewriter wouldn’t fade away.
Charlie noted that experiencing 45-plus years of shifting tech paradigms “does have a way of putting an edge in your thinking.” Sound decision-making and the benefit of some luck help to mitigate occasional missteps. So, as the AI era continues to take shape (more on this later), he feels a deliberate approach is most prudent.
“We love AI, and we’re deploying it in different ways, but you need to be careful,” he said. “For one, you can frighten a lot of people. Our job isn’t to reduce head count. Some companies think they can capitalize on it by reducing staff to grow their business. That’s the worst choice, in my opinion. To me, it’s still people that make the biggest difference. If we can make people more efficient, we can grow without maybe needing to add more staffing. But that’s not hurting our existing people.”
Spiritual Beginnings
The Usherwood boys represent the second generation at the helm of their $46 million dealership. Childhood sweethearts Charlie Sr. and Carol Usherwood launched Ontario Business Machines in 1964. He began as a technician for National Cash Registers (now NCR Voyix) and moved to Oswego, New York, before deciding to start his own firm, partnering with another couple. In 1976, the Usherwoods left Ontario Business Machines and incorporated Usherwood Business Equipment, operating the company out of their family home, a former St. John’s convent.
“When Charlie and I came home from school, we had to use the back door because my parents didn’t want us traipsing through the office,” Lou remarked, noting he and his brother often ate breakfast with the employees. “The business was very intertwined with our home lives.”
The company became an authorized Canon dealer around 1979, and young Charlie joined the fray in 1982, helping place POS products into restaurants and other businesses. Lou came on board in 1986. They opened a facility in Syracuse, with the emergence of fax machines augmenting copier sales, and it helped feed into customers’ perception of the dealer as a technology hub.
“The competitors were all selling copiers, because they were comfortable with it and making money,” Lou said. “Offering fax machines enabled us to gain share in the new market rather quickly.”
Lou purchased the company from his parents in 1997, and brother Charlie returned to the company after a stint with Electronic Data Systems, an HP company then owned by former presidential candidate Ross Perot. Both men became Microsoft certified, anticipating the IT movement at the turn of the millennium.
Growth ensued quickly as new branches were added in Binghamton and Rochester (then Kodak’s back yard). Lou wanted to be in every city within the Empire State, with the exception of the Big Apple, by 2005; the goal was reached a few years later. He also bought a pair of dealerships, the first of many deals the company has made, the most recent being 2025’s PiF Technologies acquisition.
Evolved Offerings
Today, the company boasts 19 locations and carries the Xerox, HP and Ricoh lines in addition to Canon. Along the way, the Usherwoods added video conferencing and surveillance/access offerings (Axis Communications and Verkada products), eGoldFax solutions, Hypersign digital signage and Poly Inc. (an HP subsidiary) for video conferencing. In most instances, Usherwood was an early adopter. But its cornerstone service is managed IT (including cybersecurity products) and its branded Odyssey platform.
The 2025 campaign was a rousing success for Usherwood, which achieved organizational highs in revenue and profits. After 50 years in business, Lou feels the company really hit its stride and benefits from a mature organizational structure and leadership group that continues to effectively execute on its plans. The dealer made bold strokes to augment growth: a regional sales director was added for the Connecticut River Valley and 10 new account representatives were onboarded.
“One thing we’ve been able to do is fill in some geographies with account representation,” Lou said of the influx of offices. “We tried to buffer all our areas with more manpower, and that led to a significant spike in revenue, particularly in the New England offices.”
Striking a desired balance between organic and acquisition growth is important, Charlie notes. All deals are strategic in makeup, opting for the cultural fit over simply adding sales volume. While the brothers are always on the lookout for opportunities that mesh with what they’re trying to accomplish, he sees a danger in dwelling on acquisitions.
“We do really well when it comes to employee retention,” Charlie said. “If we get it wrong with an acquisition, then it creates animosity, and you don’t need that in business. You’ve got to have calm waters at all times, right?”
“Cold and Bold”
The PiF addition was an outlier in the sense that Usherwood wasn’t as successful in gaining a foothold in New Hampshire. Based in Hooksett, PiF allowed Usherwood to connect the dots with its Vermont office in Burlington (Williston).
Usherwood embraces a “cold and bold” approach when it comes to penetrating a new market. When reps go in cold, without any existing client relationships, it’s an indication that Usherwood feels the market is underserved. Lou believes it’s an opportunity that fits well within his company’s wheelhouse.
“We’re more unpredictable as a competitor,” he observed. “We’re willing to put a stake in the ground and say this is now our territory, we’re going to start doing business in this marketplace. We haven’t made a single acquisition in all of New England, and we’ve opened 11 offices there. And when we went into Burlington cold and bold, within four months a Xerox agent approached us and asked if we’d be willing to buy their business. The same thing happened with a wide-format business. We pulled the trigger on both because it made sense and was a good cultural fit. But obviously, we don’t need to rely on an acquisition to establish a presence in the marketplace.”
Managed Magic
From building their own PCs and servers in the early 2000s to its current full-fledged and ever-burgeoning catalog, managed IT represents Usherwood’s ongoing quest to solve technology’s next riddle. Odyssey is a seven-part assessment and tailored solution process that carries the mid-sized client from consultation to a forward-looking roadmap, also incorporating managed print, communications and security. The dealer provides hardware and software recommendations, security strategies and an implementation plan, providing peace of mind to companies that can’t justify a full-time, in-house IT staff.
“The Odyssey process enables us to bring a customer on board by helping them see what their challenges are and how we can climb the Mount Everest of fixing their network and making it strong,” Charlie said. “On the security side, we outline how we can deal with the vulnerabilities on their networks, protect them from the threat actors that are going to attack them eventually and prevent it from happening. That’s our Odyssey story of how we move a client forward.”
For the past few years, Usherwood has held cybersecurity conferences that feature security experts as well as speakers from area law firms and banks. Lou’s daughter, Lindsay—the company’s in-house counsel—spearheads the initiative, which was an ideal fit considering the compliance, liability and insurance issues that have taken center stage in cybersecurity and the overarching need to ensure clients are protected. The conference centers on education and awareness, and sets the record straight during an age when clients discover the hard way that their cybersecurity insurance policies aren’t as comprehensive as they believed.
Lou notes the impetus behind the conferences is educating the masses. In forging that trust with the community, the new business opportunities will take care of themselves.
“These conferences are brand-agnostic, so to speak,” he noted. “It’s more important to teach. We’ll continue to do these types of events because the public demands it. We can do our part to help keep businesses safe.”
Responsible AI
The age of artificial intelligence isn’t only concerning to the rank and file, it’s a genuine concern among the executive team at companies such as Usherwood. Charlie points out that the careless deployment of AI leads to the unintended consequence of giving it access to your company’s network data, making it incumbent upon firms to implement governance and regulatory edicts. Usherwood is leveraging AI strategically with a system of checks and balances, and the company has provided extensive guidance to team members on the professional use of AI.
As a Microsoft shop, the dealer is partial to Copilot, but it doesn’t discourage employees from using other platforms. It’s not about micro-managing its use; Charlie wants staff to grow and leverage the technology to not only be more efficient but also enjoy their job more.
Lou isn’t a fan of “dabbling” in technologies, least of all AI, and the dealer is in the process of getting select staff certified. That will benefit Usherwood internally and enable a consultancy approach to help clients enjoy more productivity and simplify processes that allow them to grow their businesses.
“After we’re done eating our own cooking, we’ll help clients benefit from that wisdom and the investment Usherwood has made in AI,” he said. “We see that as a huge business opportunity for the consulting side of our managed IT business.”
Charting Opportunities
Moving into six additional states has placed Usherwood on a solid growth trajectory, spurring a double-digit increase in contract revenue. Lou is bullish on the ability of his company to post similar and even more significant growth in managed IT, security and surveillance, video conferencing and telephony/unified communications. His team has crushed security and surveillance through the early stages of 2026, posting a 300% increase. The managed IT business is going to “carry the day,” and Lou feels the ancillary offerings will ride their coattails.
Ultimately, all roads to success are paved by the dealer’s team members, which includes multiple generations of families. Charlie concedes that it’s getting tougher to memorize all the names as the company grows. It’s a “tough, deft act” to create a company that feels like a family, his brother observes, but when you care about people, they tend to return the sentiment.
What does caring look like? Ten years ago, a member of the shipping team tapped Lou on the shoulder and expressed an interest in entering sales. The CEO pointed out the job isn’t as easy as it looks and has more than its share of stress. It takes someone with a tough skin who can bounce back from rejection. Still, Lou admired the inquisitor’s determination and provided the opportunity. Today, that team member is one of the top salespeople on staff, a multi-year president’s club qualifier. Furnishing opportunities for people to rise above their expectations was one of the values embraced by Lou and Charlie’s parents, and it will continue when Lou’s daughters one day assume the helm.
As Usherwood continues to bloom in the northeast, Lou hopes to see the day when his dealership has one contract that covers all its services. Maybe they’ll even eclipse $500,000 revenue per employee as a result. It all comes down to continuously executing on the plan, and that’s a job best left to people.
“We’ve built out several lines of business that are becoming very formidable,” he said. “We’ve taken on a large geographic area, and we’ll continue to filter in more people. We’re going to continue to take more share in the markets where we do business. We can always do a better job for our clients and take care of them in a way we can be proud of.”
Living the Dream: Usherwood Brothers Perpetuate Ideal Working Family Dynamic
We’ve all heard the idiom “familiarity breeds contempt.” It can be especially true when that familiarity is familial. Which brings us to the oft-encountered topic of working with one’s family members.
Making a family-owned business operate smoothly in the back-office end can be problematic. It requires members to respect boundaries and not trample on one another’s oversight, which is more easily said than done when livelihoods hang in the balance. It requires patience, a shared vision and the ability to collaborate at the highest level.
Lou and Charlie Usherwood have struck a balance in guiding Usherwood Office Technology with strong contributions from Lou’s daughters, Lindsay, Leslie and Lauren. They truly enjoy working with one another, which goes back to the days when the family business resided within the home. Being that intertwined perhaps conditioned them to operate in tandem effectively.
“The ability to have relationships with family members that are non-toxic and forward-thinking makes it special, and it feels like we’ve done a good job,” Lou noted. “I was fortunate to spend 10 years in the business with my mom and dad, having lunch and dinner with them as well. We went through some tough times, but I think it bonded us.”
Charlie, too, relishes being able to work alongside his brother and believes they complement each other. “Lou is goal-oriented, like our dad, and he’s the front man,” he added. “We’ve found a way to help each other at all times, and it’s been great. I like to stay in the background on a lot of things. We play hockey together; he’s a forward and I’m a defenseman. That kind of tells the story of our lives together.”
