The night before my in-person interview with York IE, I pulled up the address to map out my route.
Google didn’t just give me the address, it gave me a photo of the building, and something about it stopped me: I know that building. A second later, it got even stranger. I know that floor. Just over ten years earlier, I’d walked onto the sixth floor of 175 Canal Street for my first day at a completely different company, and now, a decade later, I was headed back to interview for a new one, in a new role, in the exact same spot.
Getting back to the 6th floor has been a journey that can be summarized by one line: you miss 100% of the chances you don’t take. Heading into college, I never knew what I wanted to do. But, I took every opportunity that came my way. I started down the path of being a farm hand to joining the National Park Service as a Park Ranger, to ultimately landing in Tech Support for a Behavioral Health software company nearly 15 years ago.
Little did I know at the time that a tech support job would send me on a journey to find what I enjoyed most; working with clients and users to identify problems to solve and work with engineers, founders, teams collaboratively to meet the need.
Over time I navigated the path from Tech Support through Quality Assurance and landing in Product Management, learning as much as I could along the way. Each time I was given a new opportunity, whether that be to learn how to code or stand up on stage in front of 1000 members of a sales team to pitch a concept that had been put together in less than 24 hours in a Hackathon, I walked in with an open mind, a good pen (yes, despite all of the modern day tooling, I still take notes with pen and paper) and ears ready to listen.
As I navigated further into my product career, a pattern started to repeat itself: companies that had already found real traction, real revenue, real customers, but had hit a ceiling they couldn’t quite explain.
At Appcues, that meant sitting with why free-trial customers signed up and then quietly disappeared, and rebuilding onboarding so the right customers found their own value faster, instead of guessing at what might convert.
At Crayon, it meant giving customers a clearer window into their own win-loss data, work that made the product harder to imagine living without, which is its own kind of growth.
Most recently, it meant helping a growing platform stop only chasing the next sale and start keeping the customers already in the door, because no company outgrows a leaky bucket.
That one shift, planning to keep customers as deliberately as you plan to win them, is often the difference between a company staying stalled and finally breaking through. None of it came from a new tool or a clever framework. An open mind, listening ears, and a good pen were usually enough to find where the friction actually lived, align a roadmap around it, and get a stalled company moving again.
So when I stepped into 175 Canal Street, I already knew the floor before I ever stepped off the elevator. The layout is different now, the decor is different, and my old desk is now a table for lunch. Yet everyone felt familiar, like I had known them for years. Funny enough, during our conversations, Evan York and I had just missed each other at multiple companies over the years, and Mike Veilleux and Todd Dyer had worked with a previous team of mine on a large initiative back during their time at Dyn. I walked out of those conversations knowing this was a team I wanted to be part of, one where an open mind, listening ears, and yes, still a good pen, would fit right in.
That same habit, open mind, listening ears, good pen, is really the closest thing I have to a philosophy. It’s less a line and more a practice: understand the user, the business, and the people, whether they’re in the next room or several time zones away, well enough to guide gently instead of pushing hard. Build unity. Remove blind spots. Keep things visible. And once a strategy is set, the real work is only beginning.
I’ve sat in enough rooms where everyone agreed on a plan and then nothing happened to know that a plan is just a plan until someone executes it. Execution is how a plan takes shape, evolves, and becomes something real. That commitment to doing the hard work drew me to York IE as much as the people did.
That’s what I’m looking forward to at York IE: helping clients move their goals forward, and letting the strategy grow as it meets the real world, one page of notes at a time. Fate has a funny way of working, and I’m glad it did.
