Before chatting with Ann Roberts, systems administrator at Webroot, I had a pretty narrow view of what her role in the IT department required on a day-to-day basis. As it turns out, a systems administrator must wear many hats and support multiple areas of the business. Read on to learn more about this tech career path.

Webroot: Ann, tell me a bit about yourself.

Ann Roberts: I grew up in Boulder, went to the University of Colorado at Denver, and graduated with a degree in music business. I moved to New York and ended up working in the IT department at Carnegie Hall. I missed Colorado, so I moved back to Boulder after having my first child. I freelanced for a while, worked at a now defunct startup for a while, and then began my role at Webroot. I currently live in Lafayette, Colorado, with my husband, our two kids, and our dog, Max.

Carnegie Hall, that sounds amazing. Was this your entry into tech?

Yes, but by accident! I started as the assistant in the IT department at Carnegie, but there was only one technician, and I enjoyed filling in the gaps when he wasn’t around. We were a two-person team, which meant that I ended up learning a lot more than I expected, and discovered that I had an aptitude for understanding tech and systems. The rest is history!

What do you do at Webroot?

I am a systems administrator. I am responsible for the care and feeding of the systems that make up Webroot’s corporate infrastructure.

Take us through a ‘day in the life’ of a systems administrator.

It is different from day to day, but it all starts with a big cup of coffee. First thing in the morning, I check email to see if anything has gone haywire overnight. Next, I take care of any urgent requests that need attention. After that, I work on projects as time allows. One project I’ve done quite a bit of work with is with our vRealize Automation environment (Partly Cloudy, as we call it). This system allows people to create their own virtual machines on demand. It has proven especially useful for the quality assurance engineers, because it gives them a disposable platform on which to do their product testing. It has also been interesting to have a window into their role in the company.

Have you seen anything surprising or an unexpected in your field?

My previous company was the sort of environment where every time there was a technical problem, everyone flew into a grouchy panic. After the problem was resolved, inevitably there would be a rush to place blame on someone or something. The result was an environment that made you afraid of messing up. It was a great surprise after starting work at Webroot to find that when problems happen, as they do everywhere, everyone takes it in stride and works together to find solutions.

What has been your biggest challenge working in tech?

Because I found my profession by accident, I have not done any “formal” training. For much of my career, I’ve relied on what I’ve gleaned from coworkers, Google, and trial and error.

What is your biggest takeaway or lesson learned from working in the field?

Don’t panic! Keep a level head and you’ll figure it out.

Love that advice. What about students in your field, any guidance to share?

Get as much real-life experience as you can. There is only so much that can be learned by reading about a subject. The whole point of this job is to expect the unexpected, and the unexpected is what you encounter on the job.

What about professionals looking to get into tech?

If you find a subject you’re interested in, then just find a way to be around it. Take a class on it, do research on it, or set up the environment and play around with it.

What’s it like to work for Webroot?

Webroot is a fun company to work for. There is a strong emphasis on work/life balance, which is important to me.

Thanks, Ann. I think your great attitude on tackling challenges must be a great asset in your line of work.

If you’re interested in a career like Ann’s, check out our careers page at You may be particularly interested in our openings for a QA Engineer.

Ashley Stewart

About the Author

Ashley Stewart

Senior Communications Manager

Ashley Stewart has more than ten years of experience in public relations and communications, helping companies share their story with external and internal audiences. She has a passion for cybersecurity, corporate social responsibility programs and crisis communications.

Share This