Melanie Osio

When I joined CI Web Group, I was hired as Director of HR.

I stopped being HR a long time ago.

Nobody handed me a new job description. The company kept evolving, and I evolved with it. Today my title is Chief of Staff, but the real story is everything that happened in between.

Before CI Web Group, I came from ad tech. The work was fast, data driven, and built for scale, but somewhere along the way I'd lost the connection between what I was building and the people it affected. Here, every system we improve helps a contractor grow a business, hire another technician, support another family. That changes how you approach your work — and it's a big part of why I stayed through everything that came next.

When our CFO departed, someone had to keep the finances running. That someone turned out to be me. I'm not a finance person, and I didn't pretend to become one. I worked alongside our fractional bookkeeper, took over managing what the CFO had managed, and put systems in place so the financial side of the business could keep moving. I never became the expert. What I learned is that you don't always have to be — you have to be willing to sit in the seat, ask the questions, and build the structure until things run without you.

When we shifted systems and built a few of our own, I could have watched from the sidelines. HR doesn't build websites. But I wanted to understand what this company was actually building, how it worked, and what we needed to do to succeed. So I learned alongside the tech team, and I built the front end of a few websites myself. Not expert work — but enough to speak the language, enough to understand what our team lives every day. I'm on all the production calls now, not just the people-related ones, because you can't help lead a company you only understand from one department's view.

Somewhere in all of that, a lesson took hold: your job isn't something you protect. It's something you improve until it no longer needs to exist in its current form. Then you help build what's next.

That sounds exciting on paper. Living it is harder. There were weeks I questioned whether I could keep up, and days that felt like rebuilding the airplane mid-flight. The speed here is real. It forces decisions before you feel ready, exposes weaknesses quickly, and demands you learn faster than you thought you could. Through all of it, I tried to be the person who kept spirits high on the team — partly because they needed it, and partly, if I'm honest, because I did too.

But growth rarely feels comfortable while it's happening. Every one of those uncomfortable stretches was quietly turning me into someone who could handle problems that would have overwhelmed an earlier version of me. Confidence, I've learned, arrives after you've done the difficult thing. Not before.

Working alongside Jennifer changed how I think about leadership. Leaders aren't there to preserve what exists. They're there to challenge assumptions, question what no longer serves the mission, and rebuild even when what's already there is good. Watching her do that — and being pushed to do it myself — rewired the question I ask every day. It's no longer “How do I do my job better?” It's “How do I build a company that doesn't depend on me doing this job forever?”

I'm proud of the systems we've built, the problems we've solved, and the people we've grown. But that's not what I'll remember most. I'll remember becoming someone more adaptable, more resilient, and more willing to step into uncertainty than I ever thought I was.

I joined to help build a company.

Somewhere along the way, the company started building me too.