Written by Emily Glaser | Photos by Anthony Harden (May 2017)
With relationships and range, Russ Stinehour and Troy Tolle of DigitalChalk are altering the landscape of Learning Management Systems.
“Traditional methods of learning are really changing,” Troy Tolle says, leaning back in his chair, which is sitting crooked in the corner of business partner Russ Stinehour’s office. Outside, the clouds above Biltmore Park skitter across the sun, marking soft shadows on the sides of the mountains.
It’s a scene that’s idyllically Ashevillian, and at first glance at odds with the strikingly modern one inside the office of this successful international technology enterprise called DigitalChalk. But in reality, the sentiments that are fostered here are as honest, natural, and thoroughly timeless as those very mountains.
Tolle (rhymes with “Sully”) is explaining the impetus and initiative for his business: learning in a modern era. His hands unconsciously return to the same gesture of genuineness, palms up and outstretched before him. “You no longer come out of high school, and this is the set of [college] courses you need to take. Kids in high school and junior high are learning to code by taking a class online.” Whereas learning has traditionally been so structured—ladderback chairs and ruler lashings—it’s now as ephemeral and shifting as the clouds outside.
The latest generation is balancing iPods and pacifiers, but technology has leeched into every age group, influencing the way we cook, read, and sleep, so of course it influences the way we teach and learn. The places people are going to learn are different—not lecture halls, but home offices—and the way they’re learning is also different—not through textbooks or dry lectures, but through engaging, interactive, and measurable digital interfaces.
Learning Management Systems (LMS)—platforms that host content such as videos and tests—are the modern-day equivalent of a schoolroom for both big businesses that need to streamline trainings and entrepreneurs who want to share their knowledge with a broader audience. Asheville’s DigitalChalk is the proprietor of one such LMS, providing a vehicle for learning that’s innovative not just in its structure, but in its goals. Traditional methods of learning are changing, and DigitalChalk is leading the charge with both innovation and compassion.

Troy Tolle
Tracing the Dotted Lines
“LMS is a place where you manage your user base and what they’re learning,” Tolle says. He translates the acronyms and appellations of his trade into laymen’s lingo with ease. “There are two different product types: LCMS (Learning Content Management System), where you’re managing the content that you’re going to deliver to your users, and LMS, where you’re managing what users are going to experience, and your user base and tracking the content that you’re going to deliver. DigitalChalk is a blend of these two.”
Today, Learning Management Systems are savvy, cloud-based software programs that bring knowledge to users in snappy, high-quality chunks, but they’ve taken many iterations over the decades. Folks have been integrating basic computer technology with learning since 1924, when Sidney Pressey invented the first teaching machine—a cousin of the typewriter—which posed multiple-choice questions to students.
As technology evolved, so did those first ancestors of modern-day LMS. There was 1956’s SAKI (self-adaptive keyboard instructor), which adjusted the level of the questions based on the performance of the user. MIT’s “Project Athena” was unveiled in 1983, a five-year plan for exploring the integration of computers and teaching. And in 1990, SoftArc launched LMS FirstClass, the first true LMS.
But those earliest LMS were the clunky, lethargic ancestors of their modern-day counterparts, swift and agile systems like DigitalChalk. Today’s LMS combine slides, videos, and tests in sleek, cloud-based systems that are simultaneously easy to navigate and genuinely engaging.
Veteran programmers and entrepreneurs, Tolle and Stinehour have tracked and contributed to the the progression of LMS over the years. Now you’ll find hundreds of platforms willing to curate and host your content, for small businesses and large; for schools and the military; for stay-at-home moms wanting to share their recipes and part-time pilots looking to give lessons in flying. In this field of competitors, DigitalChalk stands alone.
The Men at the Board
It’s hard to imagine these humble, relaxed men as business partners in an internationally-recognized technology company. Their interactions are as casually nimble as brothers; they complete each other’s sentences, proffer up compliments and accolades for the other with gusto and receive them with “aw, shucks” humility. It’s a relationship that’s developed over the course of two businesses and nearly two decades.
The company’s president and CEO, Stinehour, is a software engineer by trade and an entrepreneur by choice. With an MBA from the University of North Carolina at Chapel Hill and a BS in engineering and system science solutions from North Carolina State University, he’s long been uniquely situated for a life of technological innovation.
He earned his chops as a senior product manager for IBM, where he worked for 17 years, before founding his first software services company, CrossLogic, in 1995. The boutique tech company built approachable interfaces for the back ends of systems that supported a host of businesses, ranging from banking to military. He grew the Asheville-based company to 50 employees (including Tolle) before selling the enterprise in 2005.
Stinehour outlines his accomplishments with methodical timelines, but the truths of his success are far less sterile. “He’s wicked good at math in his head,” Tolle interjects, eliciting a smile from Stinehour, who nods. “I can see in my head the chalkboard. I used to have this bad habit of actually writing on the chalkboard. I’ve had to learn how to do things differently.”
Learning how to do things differently isn’t just definitive of Stinehour’s business, but his life too: The entrepreneur has been legally blind, having lost 97 percent of his vision due to Retinopathy of Prematurity, a disease that afflicts premature babies. He works actively in that community, serving on the Advisory Board to the Industries for the Blind in Asheville and, previously, on the North Carolina Commission for the Blind.
His blindness has in many ways provided Stinehour with a unique set of opportunities and abilities often absent from the tech world. “If people are presenting slides or something, I don’t even pay attention, I just listen. It serves me well because I don’t read ahead,” Stinehour notes. In a tech world dominated by fast paces and short attention spans, Stinehour takes the time to slow down and observe, much to his advantage.
It’s a trait that he’s passed on to Waynesville native Tolle. The Chief Technology Officer found computer science largely by accident. “I wanted to do special effects in movies, and my guidance counselor in high school said, ‘Go into computer sciences, it’s all done on computers.’ Which was the wrong advice, but it served me well because I really loved it,” Tolle says with a laugh.
Tolle received both his BS and MS in computer sciences from North Carolina State University, and it was when he was finishing up his final degree and teaching at the university that he met Stinehour. He didn’t want to teach forever, and he’d already begun the job hunt but found many of the opportunities available deficient. Though it was, as Tolle says, “a hot time in the market for computer scientists,” gigs at big tech companies like Microsoft didn’t appeal to Tolle, who wanted an opportunity to stay engaged. He found such an opportunity with Stinehour, who offered him a job at CrossLogic. Five years later, that opportunity would expand with their founding of DigitalChalk.
There are 650,000 active users on the system who work with the 69,978 courses hosted on the platform. DigitalChalk is active on six continents and in seven different languages.
The First Sketch
While still part of CrossLogic, Tolle and Stinehour worked with a small private college in Georgia to build a learning management system. At the end of the project, and their tenure with CrossLogic, the college posed an interesting question: Would you like to take that learning management system into the marketplace?
It proved to be the impetus for DigitalChalk. Stinehour frames the process of founding the business with bullet-point finality: “I did the business planning; Troy did the technology work; we found angel investors; and in January of 2007, we launched the company.”
But in truth it was a much more nuanced, even artful, chain of events. “I can remember sitting on my couch coding what would become DigitalChalk, just me and Russ, just coding,” Tolle remembers, with a touch of wistfulness. “You just don’t know what that software is going to turn into.” At that moment, their faces lit with the cool light of a computer screen, neither Tolle nor Stinehour guessed that their idea would turn into a cross-industry, international LMS with hundreds of thousands of users.
DigitalChalk works primarily with small and medium-sized businesses (about 100 to 125 employees), and currently, those businesses number 650 active customers every month—a number that, thanks to seasonal trainings, bumps the annual monthly average to 1,300. A few of those clients are local, but the majority (about 90 percent) are national, and the other 10 percent overseas.
There are 650,000 active users on the system who work with the 69,978 courses hosted on the platform. DigitalChalk is active on six continents and in seven different languages. They’ve delivered over 42 million questions to those hundreds of thousands of users over the course of the past ten years. And all of this from their small headquarters located in our own Blue Ridge mountains.

Russ Stinehour
Drawing Something New in Scope
So what, exactly, does DigitalChalk do? At its core, DigitalChalk is unique in that it offers two distinct product lines of LMS: e-commerce and corporate. “There’s no competition in the marketplace with two products in one,” Tolle explains. “We service people who want to sell their knowledge online, as well as the corporate entity that wants to train their employees, and we do it elegantly within the same platform.”
Whereas most LMS platforms cater to one or the other—online courses or employee education—DigitalChalk accommodates both. Though the system works essentially the same for both sides of the business, the clientele are starkly different and cover an inestimable spectrum of potential users.
On the e-commerce side, which makes up about two-thirds of their business, DigitalChalk works with the largest variety of clients. “There are a lot of continuing education courses—everything from eyebrow waxing to heart surgery to flying airplanes to harnessing horses,” says Tolle. DigitalChalk works with these e-commerce entrepreneurs to get their knowledge out into the world in appealing and accessible packages.
The corporate side of the business is also varied, but those clients share similar objectives. The companies Stinehour and Tolle are working with genuinely want to train their employees, and train them well—and, in the process, track that training. “If you look at corporate investment [into] training, the estimates are somewhere around $160 billion,” says Stinehour. “There are three reasons: They want to mitigate risks, increase productivity of employees, and retain their best people.”
Regardless of their specific industry or business sector, many of these companies need the same types of trainings. “They have to spend a lot of time and resources to create these courses, but a lot of corporate customers need courses that are common to every business—things like safety, sexual harassment, diversity, and active shooter on site,” says Stinehour. DigitalChalk noticed these shared needs in their corporate customers and created a solution.
DigitalChalk subsequently worked with eight different business partners to curate a set of courses that are available for the entire spectrum of their clients. These partners, Stinehour and Tolle note, represent some of the most knowledgeable and experienced in their own industries. “If [our customers] want to mitigate HR risks, increase productivity, etcetera, not only do we have the right LMS to extend and deliver their training, we’ve got the total solution because we’ve got the content from the best of the industry,” says Stinehour. These programs are sold separately, but because of their high-volume demand, they’re affordable. The DigitalChalk website breaks down the pricing plans: a three-tiered one for e-commerce at $10 per month (the “Essential” level), $29 per month (“Professional”), or $99 per month (“Premiere”); and a plan for corporate LMS set at $249, $399, $549, and $699 monthly tiers, depending on how many users there will be. And that new curated content is already leading to more and bigger opportunities (and clients) for DigitalChalk.
When asked if their spectrum of customers and services is ever a disadvantage for the company, the response is an immediate “no.” “We help people get their content ready; we’re not the subject matter experts.” Tolle says. “Our customers are looking for a software solution. They’re saying, ‘I need to be effective with my training.’ Do we know every nuance about how to fly a plane? No, but you bet your bottom dollar we can tell you what the most effective delivery method is, how you need to style your slides or your video, who are the best people to go to, what the best length is, when or when not to use voiceover. We don’t have to know everything to be able to help somebody.”
From banks to bakers, from pilots to plastic surgeons, DigitalChalk can, and does, work with a huge range of businesses and enterprises—and that’s what makes them thrive as a business and as individuals. “I had a choice to go work for a large company,” Tolle remembers. “You could go to work for Microsoft, any of those companies, and you’d work on one project. Working with Russ broadened everything… Not only do you learn a brand new industry in a short amount of time, you have to stay on top of technology because you’re helping people do things that haven’t been done before. You have to be really fast at learning and you get to learn so much.”
Drawing Something New With Relationships
Though DigitalChalk is defined as a business by its cross-industry span, Stinehour and Tolle themselves are defined by their authenticity and appreciation of relationships. It’s apparent in the lolling lilt of Tolle’s Appalachian accent and in the slow, measured cadence of Stinehour’s voice. Their conversations include a lot of pausing, reflecting, and smiling. And those conversational idiosyncrasies always seem to drift back to relationships with each other, their employees, and their customers.
Stinehour says more than once, “We’re a relationship-driven company that just happens to have innovative technology.” It’s the unofficial tagline of DigitalChalk, and it begins with their customers. “We put the relationship with them before the technology,” he says. “You can’t have a successful small business if you don’t take care of the people who are paying you.” It’s old-fashioned business at its best: Good customer service makes for good customers.
“Our customers, when they call into support, they know who that is, and they know them personally,” Tolle says, noting that customers and support staff are on a first name basis, alluding to that old-world “mama ‘n’ dem” charm on which, in an earlier era, businesses used to thrive. And those conversations and level of compassion continue long after the phone receiver clicks. “We talk about our customers and making them successful all the time. Is it something we have that they need? If we can make them successful, then we’ll be successful.”
Stinehour poses an example. A local health company created a program and distributed it to their employees via DigitalChalk. After reviewing, the team at DigitalChalk offered a suggestion: Though the program was effective, it would be even more effective as a video. DigitalChalk introduced them to local marketing and video production company Bclip Productions. and now their content is wowing competitors at conferences across the nation.
Stinehour points out, again, that in interacting with hundreds of clients and thousands of users, it’s not just the sheer number of relationships the company is building, but the depth of them, that differentiates DigitalChalk from other LMS platforms. “We sell to businesses that train their staff, and we also get to talk to their employees. We talk to businesses that want to sell their courses online, and we’re also the first level of support for students who are buying their courses. So we talk to a lot of people.”
Stinehour and Tolle’s obvious respect for their clients is mirrored by their affection for their staff, many of whom have been with them—as DigitalChalk, CrossLogic, or in some other capacity—for decades. They consider DigitalChalk a family, and an extended family if you include the businesses they support and partner with, like Bclip, and a whole intricate spread of a family tree, with roots and leaves and stretching limbs, if you count their customers. “The only thing of any value is relationships,” Stinehour says, with a smile. “That’s what makes the business fun.”
We condemn iPhones and social media as ironic bearers of disconnection, decry the modern digital age in which we connect more often with our phones than our friends.
Erasing the Board
There’s a theory that divides the effectiveness of learning into three percentages. According to this theory, 70 percent of learning is done through experience, 20 percent through some type of live training (like a conference), and a mere 10 percent through courses delivered by LMS.
Stinehour and Tolle are both aware that LMS have not traditionally been the most effective of teachers, so they are working to change that with DigitalChalk. “We don’t want to be the 10 percent. We want to be able to capture everything for you,” says Stinehour, and Tolle chips in, “We want to be the 100 percent.” The company is intentionally integrating new facets of learning with their LMS to make it as powerful as possible.
“We’re the first LMS in the industry to fully integrate our LMS with a learning record store (LRS) through XAPI (Experience Application Programming Interface), so that we can pass experiences from LMS to the data store, so that these companies can do big data analysis,” Stinehour rattles off. In laymen’s terms, DigitalChalk allows companies to track their students’ progress, not just through traditional methods like testing, but by analyzing how they experience the LMS. When did they hit pause; what did they re-watch; how long did they spend on a certain page? These are all relevant questions that, when analyzed and digested, can allow LMS to adapt its methods and become more effective.
DigitalChalk is also actively pursuing blended learning, which combines classroom learning (or an equivalent) with online learning, whereby students have partial control of the timing and pacing of instruction. “Our LMS supports on-demand courses (video, PowerPoint, etc.), but it also supports courses that are live, like webinars and GoToMeeting,” explains Stinehour. Blended learning also means collaborating, whether that is through the chat feature already present on DigitalChalk, or the new discussion forum they’re currently working on.
Being the first to use XAPI and LRS with an LMS, or being the first to offer blended learning within an LMS—those are just the first steps in keeping their LMS relevant and effective. “It’s in our DNA to innovate,” notes Tolle. “We’re not going to sit still and say, ‘An LMS is an LMS.’ We’re going to innovate and make sure whatever is around that box is cool.”
Standing Before the Classroom
Stinehour might be described as a true entrepreneur. He refers to himself as a “blank sheet guy,” the one who makes something from nothing and does so with a smile. He recounts the founding of DigitalChalk with unfiltered pride. “When we came up with the name DigitalChalk, it had no recognition, no traction, no clients. To take it from a blank sheet of paper to something that is growing, alive, that people recognize…”
Tolle interrupts. What he says goes beyond that boastful draw of entrepreneurship and taps at something more, something that defines the purpose of DigitalChalk.
“…that supports families,” he says, picking up the thread. “When you think about it, people start their own small businesses on top of us—they can’t survive without us.” Stinehour, returning to the thread, continues, “Look at the entrepreneurs we support—that’s about two-thirds of our business. Hundreds of businesses started because we gave them the platform. How many families are being supported by DigitalChalk?”
It all goes back to those relationships—to people. So often, technological advancements are viewed in stark contrast to personal development, a weighted seesaw that pits one against the other. We condemn iPhones and social media as ironic bearers of disconnection, decry the modern digital age in which we connect more often with our phones than our friends.
But companies like DigitalChalk prove that’s not necessarily the case. They’ve taken the most modern of technologically-driven programs and turned it into a platform not just for learning, but for fostering human connection. That’s as timeless and beautiful, as shifting and evanescent, as those mountainous shadows outside.
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