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MSP Spotlights, News

March 21, 2024 |

Hard Work Pays Off: One Chicagoland MSP’s Story

The story of a technologist turned business owner that successfully switched from break-fix to managed services.

The origin story of an MSP, like that of a superhero, often is compelling. Sometimes it begins with a nontechnical businessperson embracing the challenge of entering the world of IT and learning technology on the fly.

Not Jeffrey Chang.

In 2001, his final year as a student at the University of Chicago, he took a work-study job with Chicago Microsystems of Libertyville, IL, working as an outsourced help desk for a customer on campus grounds. “When I graduated from college, I decided to continue working with them full time,” Chang recalled.

His immersion in the world of full-time technology services was intense. “All kidding aside, I was spending like 100 hours a week working. But to get ahead, you’ve got to put in the time.”

That worth ethic enabled him to advance from junior tech to senior tech and eventually to director of technology for Chicago Microsystems, which was founded as a break-fix shop and VAR in 1988 by John and Mary O’Shea. The beginnings were humble, with the office in a basement in Chicago’s suburbs.

After a long run, Chang was given the opportunity to purchase the business in 2011. He took the owners up on the offer and has been president ever since.

“I’m very technical, but being a business owner, you have to run all the other facets as well: sales, marketing, clean up duties, all of the above really,” he said. “It’s been an interesting journey — and a good one.”

Addressing the Expectation Gap

Under Chang, Chicago Microsystems slowly transitioned towards the MSP model, despite keeping some legacy clients.

Initially, the idea to evolve the break-fix shop model caused major trepidation because the company was doing fine with the old model, Chang shared. “You don’t want to bite the hand that feeds you, but we could definitely see that the the future was in managed services.”

Under the prior model, sending techs to customer sites on a regular basis was a large revenue driver. But when the economy slowed, customers started canceling their weekly recurring visits. “When we did go on site, we asked if they realized that their backups weren’t working or things like that,” Chang said. “Although it was their obligation to stay on top of that, they couldn’t because they were busy running their own businesses.”

The break-fix model left customers with an expectations gap. There was also a disconnect for some customers who knew they weren’t paying for tech support monthly but still thought Chicago Microsystems was responsible when things broke. That was exacerbated by years of complimentary services that customers came to expect during onsite visits, he explained.

“So, we started off with the basics. We mandated managed antivirus, managed patch, managed backups. We started developing all-you-can-eat plans. We rolled out an RMM tool and a PSA tool to manage it all.”

The business grew but didn’t become overly specialized or narrowly focused. Although Chicago Microsystem’s clientele is similar in size, it spreads across many industry verticals.

“That provided us with natural diversification,” he noted. “When COVID hit, some customers were struggling while others were going like gangbusters. That balanced with some net benefit for us. I think it’s important to insulate yourself from a downturn in any one industry.”

From Owner to Leader

Although the IT industry is competitive, it’s a community that Chang is proud to be a part of. “At the end of the day, I’m not afraid of the competition. There’s plenty of business out there and you realize that you can definitely make a good living while still making friends,” he explained.

He’s also passionate about contributing wherever he can, including at events like the recent ChannelPro LIVE: Chicago event near his home.

“I love to share; that’s just part of my DNA. If I can help other businesses and other people who are struggling to grow, that’s good for everybody. That willingness is an important part of leadership,” Chang remarked.

The importance of openness and candid conversation carried forward as he shared his thoughts on vendor relationships.

“The expo hall time here [at ChannelPro LIVE: Chicago] has been helpful because I can meet vendors and engage with them. It’s not just a pitch; we can talk about business issues. I can have a direct conversation. It’s important to stay on top of solutions. Events like this are great for that because there just isn’t time to do it the rest of the year.”

100% Satisfaction Guaranteed

One of the prominent features of Chicago Microsystem’s homepage is a satisfaction guarantee. It’s an age-old approach in sales and marketing that has been extremely successful for some MSPs.

“The sales pitch I use, it’s very much a representation of me and my approach to things,” Chang shared. “We’re a small business, but we’re thorough and we communicate well. To win over other small businesses, we work with the stakeholders to articulate their needs. I really try to understand their businesses. My mantra is that technology is just a tool to achieve their goals.

“The satisfaction guarantee is part of that, a little extra assurance that we’re trusted advisors and we’ll help them weigh the pros and cons and make the right choices.”

Breaking the $2M Barrier

As a result of the hard work, Chicago Microsystems in 2023 eclipsed the $2 million mark in revenue for the first time. His advice is to IT businesses that are hovering around the $1 million mark and can’t seem to break through to the other side was to be introspective and look at what you’re doing to earn the money. Here are several of his insights related to taking things to the next level:

  1. As you grow, you realize that time is a resource: “Be conscious of where you devote your time. If you’re gaining efficiencies and closing tickets faster, you intuitively think that customers will be happier. But there’s the other side of the coin, where it’s like you’re just punching a clock. It’s important to not devalue the value prop by not giving the customer service attention, the personal touch that they’re looking for. So, for a newer MSP, start to study where the numbers are coming from. How time and money is being spent.”
  2. Take on new lines of business: “We added telephony, physical cameras, physical security access controls. They aren’t a strategic focus of our business, but we take advantage of the opportunities that crop up from our existing business.”
  3. Pick up MRR where you can: “For example, we do referrals for payment processors. There are master agent relationships to sell Comcast or AT&T. Once you book those things, the commissions keep coming in and you don’t have to do anything extra to earn them.”
  4. Invest in tools: “In the beginning, it might look like a tool costs too much, but if you’re using them smartly, they earn that back and more. It can take many months, but a mature stack can really bear fruit.”


President, Chicago Microsystems

  • Founded: 1988
  • Location: Libertyville, IL
  • No. of Employees: 6
  • Website:
  • Company focus: We are a managed service provider that seeks to empower our clients for success through the better use of technology.
  • Professional memberships: ASCII
  • Recommended book: “The Pumpkin Plan”
  • Favorite part of my job: Learning the business of my customers and solving their issues.
  • Least favorite part of my job: Not having enough time to do all that needs to be done.
  • What people would be surprised to know about me: While I appreciate technology, I might be even happier if most of it did not exist.

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Hard Work Pays Off: One Chicagoland MSP’s Story

March 21, 2024 |

The story of a technologist turned business owner that successfully switched from break-fix to managed services.

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