28 February, 2022

Profiles in IT – Jason Ross

As we continue to profile and highlight our IT technicians, we keep learning new things about the people we’ve worked with, even the longest-tenured among us!

As we continue to profile and highlight our IT technicians, we keep learning new things about the people we’ve worked with, even the longest-tenured among us! This week, we sat down with Tech Superpowers (TSP) Senior Engineer Jason Ross to discuss his beginnings in IT, his current role, and what excites him about the future. A “grizzled tech veteran” (in his own words), Jason is a constant source of information and mentorship for our newest employees. Check out our conversation with him below and see why Jason is one of our most valued team members!

What sparked your interest in IT?

As far back as I can remember, I’ve always been interested in computers, even as a little kid. When my friends and I used to play Teenage Mutant Ninja Turtles, I was always Donatello because I always wanted to hack the computers, get into the systems, and be the technology guy. Early in life, I was always tinkering with stuff. My dad was an engineer, so our basement was filled with tools and toys. I would always try to make these really elaborate Rube Goldberg devices in my bedroom to turn off my lights or radio from my bed.

So I think I’ve always been interested in computers, just absorbing what I can. I remember buying this Macworld Mac Secrets book by David Pogue in the 90’s and poring through it page by page.

By the time I got to high school, I kind of just fell into maintaining the Apple computers at school. I was the one kid who was super interested in them. That led to me starting my own small business when I was in my late teens and early twenties. I would do basic Mac repair around the North Shore, just driving around in my car helping users with their computer problems. After doing that for a bit, I became the Mac guy at CompUSA. I left tech for a while doing other jobs like working for Home Depot, Line Cook at an Italian restaurant, and Bed Bath and Beyond (where I met my wife). One day I received a call out of the blue from a recruiter at Apple for a position at the Genius Bar. I stayed with Apple for almost 8 years before I came on board at TSP.

How did you transition to help desk support with your history in hardware repair?

I’ve always enjoyed talking with people and helping them out. I attribute that to my mother, who raised me with very traditional oldschool manners. I quickly learned that good manners get you far with people and open the doors of understanding when working on problems. Gaining those soft skills early in life set me up for success in IT. Troubleshooting has always been fun for me because I enjoy working with people to solve their problems. The training I received at Apple was really paramount, too, for learning how to troubleshoot and fix software issues. Working there for eight years really prepared me for TSP’s managed services. I love tinkering and working on hardware, but as the industry has shifted away from technicians doing physical repairs, I’ve had to adjust as well.

Beyond helping clients, what is it you do at Tech Superpowers?

My role at TSP consists of not only working the help desk, but I also operate as the help desk Dispatcher. I run the ticketing system and assign tickets to technicians depending on the level of skill required and the time needed. Outside of the day-to-day responsibilities, I’ve also been involved in many networking projects at TSP. Right now that’s my current passion, architecting network redesigns or finding solutions to existing network issues for our clients.

Being one of the more senior techs at TSP, I also take on the role of mentorship for new employees. When new team members come on board, I actively reach out to them and offer my support, not just for technical knowledge but also for emotional and moral support. This job can be very tough mentally and emotionally at times. Fixing people’s tech issues is not always easy or straightforward, and you’re helping clients when they are at their most frustrated. When i first started at Apple, they had a mentorship program, and my mentor left a big impression on me. I wouldn’t have lasted at Apple if it wasn’t for him. He gave me the tools and tips to survive and thrive in the IT workplace. So I like to pay that forward and be that person for other people in the industry.

What’s one project at Tech Superpowers you have been particularly proud of?

We did the network design with the Celtics at their new practice center in Allston. I was heavily involved with that and actually went on-site and help set up and configure all the Meraki gear. I was there at the practice center when they were doing the wiring and had thousands of contractors on site. We were just one in a sea of people, and it was cool to see it all come together. Being a local Bostononian, it was really cool to work with the hometown basketball team. It is always a fun bragging point in conversations!

What is something on the horizon for IT that interests you?

I think the world is going to have a reckoning when it comes to cloud-based solutions and online services. Especially as the web becomes more and more centralized. We all think the of the web as this decentralized platform. But when AWS goes down, you see hundreds of websites and services go offline. I think we’re going to see that more and more as the infrastructure of the US starts to fail. Our electrical grid is ancient. As more systems begin to go down and become unreliable, I think you’re going to see a trend of companies coming back to internal systems and servers. You’ll see companies dropping cloud platforms and building their own solutions. There’s an old saying in tech that the cloud is just somebody else’s computer. As this computer fails, people will start focus more on keeping everything in-house.

What advice would you give to someone who is interest in IT or just starting out?

Tinker, tinker, tinker. Get yourself a Raspberry Pi and mess around with it. Try installing Arch Linux on a system. You’ll learn so much about how a computer works and how things operate in it. Even though it’s Linux, the fundamentals are still the same. My other advice would be to find yourself a mentor and really lean on their knowledge and experience. Having a mentor was instrumental to my growth in IT, and they prepared me for success in this field.


At Tech Superpowers, we believe IT is a human issue. That’s why you won’t find our techs hiding out in server closets or typing away in a dark room. They’re client-facing and happy to help you with your tech problems, no matter how large or small. Our techs are what makes Tech Superpowers great, and we love putting them front and center, putting a face to the name you talk to whenever you have computer issues. If you haven’t already, check out our profiles on Adam Fisk and Paulo Rodrigues. Ready to bring Tech Superpowers to your organization? Contact us to get started!

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