{"id":68827,"date":"2026-03-19T15:39:08","date_gmt":"2026-03-19T22:39:08","guid":{"rendered":"http:\/\/www.enxmag.com\/twii\/?p=68827"},"modified":"2026-03-20T07:10:35","modified_gmt":"2026-03-20T14:10:35","slug":"to-grow-or-source-homespun-managed-it-professionals-pivotal-to-dealer-success","status":"publish","type":"post","link":"http:\/\/www.enxmag.com\/twii\/feature-articles\/2026\/03\/to-grow-or-source-homespun-managed-it-professionals-pivotal-to-dealer-success\/","title":{"rendered":"To Grow or Source: Homespun Managed IT Professionals Pivotal to Dealer Success"},"content":{"rendered":"\n
\"\"<\/figure><\/div>\n\n\n\n

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?<\/p>\n\n\n\n

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\u2019ll invest a decent amount of coin in coaching up IT pros, and risk having them export their talents to parts unknown. It\u2019s the cost of doing business; some organizations take it as a compliment that their team members are coveted, as it validates their development system.<\/p>\n\n\n\n

This week\u2019s 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.<\/p>\n\n\n\n

\"\"
David Carson, Plus Inc.<\/figcaption><\/figure><\/div>\n\n\n\n

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.<\/p>\n\n\n\n

\u201cWe like to train people our way, we want them to have good instruction,\u201d Carson noted. \u201cMost 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.\u201d<\/p>\n\n\n\n

Blended System<\/strong><\/p>\n\n\n\n

\"\"
Shelly Caldwell, Marco<\/figcaption><\/figure><\/div>\n\n\n\n

Some companies opt for the hybrid approach, such as Marco of St. Cloud, Minnesota. Shelly Caldwell, the company\u2019s 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\u2014cybersecurity, cloud architecture and AI enablement, to name a few.<\/p>\n\n\n\n

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.<\/p>\n\n\n\n

\u201cBy combining internally developed talent with strategic external hiring, we maintain the scale, expertise, and agility required to support our growth,\u201d she said.<\/p>\n\n\n\n

\"\"
Keith Adams, Les Olson IT<\/figcaption><\/figure><\/div>\n\n\n\n

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.<\/p>\n\n\n\n

\u201cWhen it comes to higher skillsets, it can be harder (but not impossible) to find the right people,\u201d Adams noted. \u201cWhat is harder to find are people who understand MSP-style work and have the mental flexibility that is required.\u201d<\/p>\n\n\n\n

\"\"
Travis Jack, Fraser\/Watchkeep<\/figcaption><\/figure><\/div>\n\n\n\n

While Watchkeep\u2014the managed IT division of Fraser Advanced Information Systems of West Reading, Pennsylvania\u2014is 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\u2019s culture and commitment to client outcomes.<\/p>\n\n\n\n

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. \u201cThe program is designed around industry best practices and mapped to specific job rules,\u201d he noted. \u201cIt\u2019s been running for over three years and has delivered outstanding results both in employee growth and service quality.\u201d<\/p>\n\n\n\n

Jack points out that senior-level engineering personnel are among the most difficult roles to hire. It\u2019s at this level where the onus is placed on finding professionals who \u201ccombine deep operational awareness with the agility and mindset to serve multiple clients in a fast-paced environment\u201d as opposed to technical gaps. That\u2019s expertise that tends to be highly specialized, he says, and matching their strengths with the demands on the role can be a challenge.<\/p>\n\n\n\n

This is why organizations like Watchkeep invest in talent early via culture, training and mentorship. \u201cWe\u2019re 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,\u201d Jack added.<\/p>\n\n\n\n

Shaping Clay<\/strong><\/p>\n\n\n\n

\"\"
Lindsay Usherwood, Usherwood Office Technology<\/figcaption><\/figure><\/div>\n\n\n\n

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\u2019s not always the case where the \u201cright person has the right skills.\u201d In other words, the more culturally-fit individual could be molded into the job.<\/p>\n\n\n\n

\u201cSome of our best success stories have been finding the right person for our culture and enabling them to learn and grow,\u201d she said. \u201cWe have a strong education program in the IT space where employees can earn pay increases or one\u2011time 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.\u201d<\/p>\n","protected":false},"excerpt":{"rendered":"

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\u2019ll invest a decent amount of coin in coaching up IT pros, and risk having them export their talents to parts unknown. It\u2019s 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\u2019s 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. \u201cWe like to train people our way, we want them to have good instruction,\u201d Carson noted. \u201cMost 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.\u201d Blended System Some companies opt for the hybrid approach, such as Marco of St. Cloud, Minnesota. Shelly Caldwell, the company\u2019s 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\u2014cybersecurity, 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. \u201cBy combining internally developed talent with strategic external hiring, we maintain the scale, expertise, and agility required to support our growth,\u201d 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. \u201cWhen it comes to higher skillsets, it can be harder (but not impossible) to find the right people,\u201d Adams noted. \u201cWhat is harder to find are people who understand MSP-style work and have the mental flexibility that is required.\u201d While Watchkeep\u2014the managed IT division of Fraser Advanced Information Systems of West Reading, Pennsylvania\u2014is 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\u2019s 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. \u201cThe program is designed around industry best practices and mapped to specific job rules,\u201d he noted. \u201cIt\u2019s been running for over three years and has delivered outstanding results both in employee growth and service quality.\u201d Jack points out that senior-level engineering personnel are among the most difficult roles to hire. It\u2019s at this level where the onus is placed on finding professionals who \u201ccombine deep operational awareness with the agility and mindset to serve multiple clients in a fast-paced environment\u201d as opposed to technical gaps. That\u2019s 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. \u201cWe\u2019re 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,\u201d 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\u2019s not always the case where the \u201cright person has the right skills.\u201d In other words, the more culturally-fit individual could be molded into the job. \u201cSome of our best success stories have been finding the right person for our culture and enabling them to learn and grow,\u201d she said. \u201cWe have a strong education program in the IT space where employees can earn pay increases or one\u2011time 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.\u201d<\/p>\n","protected":false},"author":166,"featured_media":68828,"comment_status":"open","ping_status":"open","sticky":false,"template":"","format":"standard","meta":[],"categories":[1650,82,87,1638],"tags":[2738,4400,545,2242,3932],"_links":{"self":[{"href":"http:\/\/www.enxmag.com\/twii\/wp-json\/wp\/v2\/posts\/68827"}],"collection":[{"href":"http:\/\/www.enxmag.com\/twii\/wp-json\/wp\/v2\/posts"}],"about":[{"href":"http:\/\/www.enxmag.com\/twii\/wp-json\/wp\/v2\/types\/post"}],"author":[{"embeddable":true,"href":"http:\/\/www.enxmag.com\/twii\/wp-json\/wp\/v2\/users\/166"}],"replies":[{"embeddable":true,"href":"http:\/\/www.enxmag.com\/twii\/wp-json\/wp\/v2\/comments?post=68827"}],"version-history":[{"count":1,"href":"http:\/\/www.enxmag.com\/twii\/wp-json\/wp\/v2\/posts\/68827\/revisions"}],"predecessor-version":[{"id":68829,"href":"http:\/\/www.enxmag.com\/twii\/wp-json\/wp\/v2\/posts\/68827\/revisions\/68829"}],"wp:featuredmedia":[{"embeddable":true,"href":"http:\/\/www.enxmag.com\/twii\/wp-json\/wp\/v2\/media\/68828"}],"wp:attachment":[{"href":"http:\/\/www.enxmag.com\/twii\/wp-json\/wp\/v2\/media?parent=68827"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"http:\/\/www.enxmag.com\/twii\/wp-json\/wp\/v2\/categories?post=68827"},{"taxonomy":"post_tag","embeddable":true,"href":"http:\/\/www.enxmag.com\/twii\/wp-json\/wp\/v2\/tags?post=68827"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}