CompanyCam

In June 2019, I was happily freelancing as a consulting product designer and developer. I’d known Luke at CompanyCam for a long time, and asked if he needed an extra Product Designer to augment his team.

He said, “That sounds cool… but it’d be cooler if you came to work for CompanyCam full-time, maybe even running the product team.”

And so began my wild-but-fun, relentlessly resourceful, 4-year journey at CompanyCam. I joined the 30-person team, shipping design improvements to the app.

Time to Scale: Ops Leadership

Soon, Luke and I realized he needed help on the administrative side of the business. I’d done generalist operational work “on the side” for startups (I’m naturally a responsible organizer). But now it was time to put those skills to work.

We needed to scale, attract investment, and achieve the big visions Luke had.

I stepped into a product and operational leadership role, standing up systems like OKRs and Core Values to keep us aligned, a Notion-powered intranet, a scalable org structure on both the product+engineering team, scalable hiring processes, continuous performance reviews, and the like.

Luke stayed in front with the vision, and I “kept the trains running on time” as they say. I built out a Product Management team. I hired designers, engineers, and administrative roles. I managed the day-to-day of the company so Luke didn’t have to. I promoted a Director of Engineering and Director of People to continue to scale.

We kept growing. We raised a Series A and Series B (in which the company was valued at ~$550MM). We went from 30 people to 200 people, from $3.5MM ARR to $24MM+ ARR three years later. (Fun fact: they’re now well over $50MM ARR.)

As we continued to grow, I handed the reigns of product back to Luke and Tifany. Kevin and Chad were capable of running engineering. We hired an excellent, seasoned COO (and later President) in Hank. I moved into a VP of Operations role to continue to help us achieve our goals.

Back to Product

But soon, my roots in product design and development proved too strong to ignore. I wanted to get my hands dirty again. I rejoined the Product Design team and immediately began working on our new Trusty product: providing the best way for people to work with good contractors.

After a few months, it became clear that Trusty needed holistic and generalist (resourceful?) leadership. Luke once again put me in charge of the small but mighty team to help it become what it needed to be. I got the product and first few key features off the ground, setting a vision and path forward for the team.

Discovering What I Really Wanted

While I was happy to help CompanyCam, and loved the people I’d met and worked alongside, I increasingly felt an itch.

I’d proved I could do well in a high-stakes leadership position at a scaling startup. People told me I was doing great, every day. But the work left me too drained to enjoy my family and the most important parts of my life. I realized I needed to get back to making things independently, at least for a while. I amicably parted ways with CompanyCam after four years, knowing they were on the path to continued success.