For many years, the conversation regarding how to enter the field of managed IT discipline centered on three options: buy, build or partner. How does that equation apply to personnel? Is there an ideal scenario?
Hiring experienced managed IT professionals is, as everyone knows, a pricey proposition and rightly so. Once a dealership has scaled its IT department, it can be methodical and deliberate in cultivating talented personnel. The fear is always that you’ll invest a decent amount of coin in coaching up IT pros, and risk having them export their talents to parts unknown. It’s the cost of doing business; some organizations take it as a compliment that their team members are coveted, as it validates their development system.
This week’s State of the Industry report canvasses dealer insights on the grow-versus-import question. We also ask them to weigh in on the skill sets/positions that prove most tricky to staff.
A certain timber of personality can lend itself to being an ideal persona for managed IT leadership. David Carson of Plus Inc. tells an interesting story in that regard. Back in the 1990s, Plus had a pair of newcomers who had recently completed their hitch with the U.S. Navy. By the early 2000s, both had moved on to become IT directors for large entities. Roughly 15 years ago, both returned to the fold at Plus, having picked up skills elsewhere in addition to the education they received from the Greenville, South Carolina, dealership.
“We like to train people our way, we want them to have good instruction,” Carson noted. “Most of our IT team is guys out of college with a degree, and we train them on up-and-down-the-street operations. We also get plenty of training and certifications from the lines of business we represent.”
Blended System
Some companies opt for the hybrid approach, such as Marco of St. Cloud, Minnesota. Shelly Caldwell, the company’s managed service director, notes the dealer grooms talent through structured leadership, upskilling and specialized training. Experienced professionals are scouted out for scenarios where advanced skill sets are needed—cybersecurity, cloud architecture and AI enablement, to name a few.
Not surprisingly, those skills are difficult to source. Caldwell cited cloud and security architecture, AI engineering and automation, advanced detection and incident response, and strategic IT maturity consulting as being most coveted.
“By combining internally developed talent with strategic external hiring, we maintain the scale, expertise, and agility required to support our growth,” she said.
Blending company-developed and outside expertise has been the MO employed by Les Olson IT, the venerable Salt Lake City firm. Keith Adams, the vice president of IT, notes the company is always monitoring rising stars who demonstrate a desire to improve their skillsets or advance their capacity, and will also look outside the office to source impact players.
“When it comes to higher skillsets, it can be harder (but not impossible) to find the right people,” Adams noted. “What is harder to find are people who understand MSP-style work and have the mental flexibility that is required.”
While Watchkeep—the managed IT division of Fraser Advanced Information Systems of West Reading, Pennsylvania—is always open to importing personnel when needed, the preference has long been to cultivate its managed IT talent. The upshot, according to Travis Jack, the vice president of service delivery, is guaranteeing a team that is technically strong and, perhaps more importantly, deeply aligned with the organization’s culture and commitment to client outcomes.
To that end, the dealer created the Watchkeep Ramp Program, which Jack describes as a structured platform bolsters the engineering team’s skills across core disciplines like cloud, cybersecurity and infrastructure. “The program is designed around industry best practices and mapped to specific job rules,” he noted. “It’s been running for over three years and has delivered outstanding results both in employee growth and service quality.”
Jack points out that senior-level engineering personnel are among the most difficult roles to hire. It’s at this level where the onus is placed on finding professionals who “combine deep operational awareness with the agility and mindset to serve multiple clients in a fast-paced environment” as opposed to technical gaps. That’s expertise that tends to be highly specialized, he says, and matching their strengths with the demands on the role can be a challenge.
This is why organizations like Watchkeep invest in talent early via culture, training and mentorship. “We’re proud to have a high-performing team that has grown up inside Watchkeep, with a shared understanding of what it means to deliver service that goes beyond expectations,” Jack added.
Shaping Clay
Seeking out the ideal fit for a team can be a tricky proposition. Lindsay Usherwood, general counsel for Usherwood Office Technology, points out that it’s not always the case where the “right person has the right skills.” In other words, the more culturally-fit individual could be molded into the job.
“Some of our best success stories have been finding the right person for our culture and enabling them to learn and grow,” she said. “We have a strong education program in the IT space where employees can earn pay increases or one‑time bonuses for furthering their education. The goal is to support growth at every stage of a career, whether someone is just starting out or has decades of experience.”
