Member Profile: PathWise IT

As a trusted Managed Service Provider (MSP), PathWise IT delivers the proactive support, protection, and clarity organizations need to thrive, including managed IT services, co‑managed IT support, cybersecurity, cloud services, and disaster recovery solutions. We sat down with CEO Christopher Olson to talk more about the company.

Tell us a little about PathWise IT.
PathWise IT is a local IT and cybersecurity company serving businesses in the Springfield/Eugene area. At a basic level, we help keep technology running the way it should so it is not slowing people down. The name PathWise IT is inspired by Sherpas, the people who help others reach the summit. They are not the ones in the spotlight, but they play a critical role in helping others succeed – that idea really stuck with me. Our job is to support our clients, guide them, and help them move forward.

“We are not just there to fix issues as they pop up. We are there to help businesses stay organized, think ahead, and make better use of their time.”

– Christopher Olson, CEO, PathWise IT

How did you get started in your industry?
I have been in IT for over 20 years now. Like a lot of people in this field, it started with helping fix things, building websites, troubleshooting computers, and just figuring things out as they came up. That led to time at the University of Oregon, working with a local nonprofit refurbishing computers, and eventually into Managed IT Services. Over the years, I have been involved in supporting, building, and growing IT environments for businesses ranging from local organizations to larger companies. PathWise IT is really about bringing that experience back to the local community and doing things the right way.

What services do you offer and what makes PathWise IT different?
We help businesses with their day-to-day IT support, cybersecurity, phone systems, and planning around how everything fits together. But the difference is really in how we approach it. We are not just there to fix issues as they pop up. We are there to help businesses stay organized, think ahead, and make better use of their time. A phrase I come back to a lot is “highest and best use of time.” Business owners and their teams should be focused on what they are great at, not chasing down tech issues or trying to piece things together. We take that off their plate so they can stay focused on what actually moves their business forward. At the end of the day, it comes down to doing the right thing. Always. That guides how we support people, how we communicate, and how we make decisions.

What do you like most about your work?
The people are a big part of it. Every business has its own way of operating, and getting to understand that is something I really enjoy. But what stands out the most is the impact. IT tends to only show up when something is broken, so it gets a bit of a bad reputation. And honestly, that is understandable. What I enjoy is being on the other side of that. When things are set up well and supported the right way, it actually makes people’s lives easier. Teams are less frustrated, things run smoother, and there is just less stress around it all. Being able to help create that kind of environment for a business is what makes the work meaningful.

Any advice for others?
Do not wait until something turns into a big problem before dealing with it. Small issues in IT have a way of snowballing. What could have been a quick fix can turn into downtime or a much bigger headache if it sits too long. Also, do not feel like you have to fight your technology or figure everything out on your own. The right partner should make it easy to ask questions and get help without hesitation. A quick call at the right time can save a lot of time, money, and stress.

Anything else you’d like to share?
We are proud to be part of the Springfield/Eugene business community. A lot of what we do comes down to relationships, and that is something we really value. Even if it is just a conversation, I always encourage business owners to ask questions and make sure they understand what they have in place. A little clarity can go a long way.

More about PathWise IT
PathWise IT was founded on a simple belief: technology should serve people – not the other way around. They deliver holistic strategies that empower organizations to reach peak performance with confidence and clarity. With over 20 years of foundational industry experience, they bring a grounded, strategic focus to every partnership – helping organizations operate, evolve, and lead with purpose.