Staff & Training

The Operations Journey with Caitlyn Young-Gilbert

Ryan Chan

We talked with Caitlyn Young-Gilbert, UpKeep’s Chief of Staff, to hear her journey from working in social impact to suddenly working at a tech startup, where she built an entire department from the ground up. We are excited for you to hear her story!

The Secret Master Plan

Until 2018, I had never worked in the tech-space before, nor had I worked a day in maintenance and reliability. When I told my friends and family about my new gig at a tech-startup called UpKeep, I got quite a few excited, but flummoxed, expressions.

Up to that point, I had spent all of my career in the social impact space. I had helped celebrities start and run their own philanthropic organizations, coordinated Fortune 500 companies’ partnerships with non-profit organizations, and ran a national non-profit organization on a shoe-string budget. Everything up until my career at UpKeep screamed, “I’m going to start a non-profit pretty soon!” And, here I was telling my friends about this really nifty CMMS software.

”From the outside looking in, the switch seemed like a wild detour. But, my jump to UpKeep made total sense to me in my secret master plan.”

How It All Started

I was the company’s first full-time Operations hire and my responsibilities could be broken into two major buckets:

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  1. Keep the business running by acting as the glue that keeps it all together.
  2. Foster a culture of learning and caring at UpKeep.


I teamed up with Ryan, the CEO, to start a tag-team Operations Department that did everything from submitting employee parking forms, to throwing celebratory lunches and running board meetings. We did every and any task needed to keep the business running smoothly, no matter how big or how small. We learned a lot in those early days – like how you should always have back up office supplies and how to move an entire office 10 floors overnight.

Once we settled into our first official headquarters and got into a rhythm of keeping the company’s Operations running in the background, Ryan and I started dedicating ourselves more and more to experimenting as much as possible. Any new idea that didn’t fit nicely into a department’s responsibilities was ours to take on. Running social media, implementing accounting software, recruiting new teammates, launching a podcast, designing swag – we tried everything at least once!

As a department, our responsibilities now included trying new things quickly to establish if it could work for our business or not. We laid the foundation for other departments to do things even better once we validated success. Some of our experiments were big wins – like banking on the hypothesis that high-quality content would be valuable to our community – but not all of them. I’ve never been someone comfortable with failure, but at UpKeep, every experiment is taken on with such a positive spirit that even when you ‘fail,’ you feel excited about the work that went into at least trying.

Expanding the Ops Team

”One of the best parts of my job has been hiring and mentoring incredible talent.”

New Ops members were never required to have Operations or tech experience, but they all joined with a passion for helping their team and taking on big ideas. We grew the Operations team as our experiments worked. And slowly but surely, our Project Coordinators have become owners of entire business functions – from office management to content and social media. I’m so proud when one of my direct reports is promoted, even when it’s to a different department, because I know they will always bring the Ops’ spirit of “Assist, Appreciate, Anticipate” to all that they do.

Building a World-Class Company Culture

UpKeep was named one of Inc.’s Best Workplaces of 2020!

Establishing a people-first culture at UpKeep has always been one of Operations’ most important responsibilities. We’ve made it a priority to focus on fostering a culture that puts customers first, demonstrating the gold-standard of transparency, prioritizing progress over perfection, and allowing people to experiment without fear of failing.

We know that creating this culture starts with recruiting and onboarding. It is our departments’ responsibility to make sure that every single new hire at UpKeep receives a high-quality, fun, and educational two-week onboarding experience.

”My goal was to always have a new hire leave their first day excited to call their friends and family to gush over how great their introduction to the company was.”

Every time we make a new hire, we as a company are so incredibly thrilled to have a new teammate. We want to make sure they feel that excitement from the moment they walk in. Establishing a great onboarding experience for our entire company is one the accomplishments I’m most proud of.

Obstacles to Overcome

Throughout this journey, there were also some hurdles we had to overcome. One problem we’ve run into as the Operations Department has grown is that because Ryan and I moved fast in the early days, we never made a ton of documentation to help others pick up the processes quickly. So, much of our Project Coordinators’ onboarding was shadowing me and me answering questions as they came up. Where does a certain paperwork live? Third shelf, yellow folder. Who do we contact to get this fixed? I usually just YouTube it. What’s the process for doing that? Only so-and-so knows, ask them – and so on. An Ops team members’ onboarding period is critical, and I realized that it was time to slow down and start creating documentation so others can take on responsibilities and make them 1,000% better. We’re progressing here each day! 

Where We Are Now

Two years, three offices later and the Operations Department is still acting as the glue that keeps the company together. We’re still fanatically focused on culture, we’re still trying new things, and we’re still having a ton of fun. Now, our sights are set on taking our experimental mindset and people-first culture and bringing it to our wider maintenance and reliability industry.

Through our community efforts, we want to create spaces where individuals in the maintenance industry lean on each other to learn and thrive. We want to go above and beyond to serve our industry’s people base – a notoriously underserved group. We want to walk the walk by supporting causes that uplift the entire maintenance industry.

”We have a responsibility to continuously honor the important work happening in our industry, and to signal boost these wins to the outside world.”

All the while, we’re focused on fostering the next generation of great innovators in maintenance.

Back to The Secret Master Plan

This brings me back to my secret master plan: I wanted to make a difference in the world, and I wanted to build something from the ground up. But, I had a feeling that nonprofits, with their dedication to convention and risk-averse nature, weren’t the future of doing good. I wanted to prove that doing good, and doing well as a business were not inherently at odds. In fact, both are needed for true success. What better way to be a force for good than to help build a start-up that cares about people above all else? If a business is motivated to innovate constantly in order to make schools safer, wastewater treatment facilities more effective, and hospitals more efficient – isn’t that one of the most powerful examples of impact a group of people can have?

I guess my secret master plan isn’t so secret anymore…

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