Katie Fitzgerald has over 15 years of experience as an investor-turned-operator and has made a career out of helping businesses grow, most recently with Faire. She joined Waystation AI as Chief of Staff.
Connect with her on LinkedIn.
10 years and 1 day in the making.
I recently spent a day with Ryan Caldbeck at Waystation AI’s office shadowing him through a typical day: calls with customers, prospects, advisors, candidates; team huddles. In between, we talked about AI-native services and the conference room camera that was bugging him.
A few meetings in, Ryan started introducing me as though I already worked there. I think we both knew how the day was going to end. Here’s why:
Waiting for the right problem
Ryan and I worked together at CircleUp ten years ago. We’ve been saying we should do it again ever since — in the way people do when they mean it.
The theme across my career has been empowering great companies, many in consumer, to be successful. At CircleUp, we provided growth capital to consumer companies. Most recently, I spent 5 years building Faire, which helps brands and retailers grow sales. At Waystation AI, we are focused on margin, arguably the one that matters the most.
Imagine a $200M snack brand running $80–100M in ingredient spend through a shared inbox, a couple of Google Sheets, and memory. Quotes as PDFs. CoAs with inconsistent naming. Spec revisions sent as reply-all. None of it is structured, so none of it is usable when it matters. This has real consequences. The impact on margin when RFPs or price comparisons aren’t effectively actioned. The loss of the Costco account because the ingredients didn’t show up in time. The loss in revenue from a product that hasn’t launched because the right ingredient is hard to find. This is what Waystation AI is built for.
The inbox problem
Procurement already has a system of record: email. Quotes, spec sheets, CoAs, lead times, terms, the price change a supplier mentioned in the third paragraph of a Tuesday reply — it’s all there, spread across thousands of threads and a few hundred spreadsheets.
To fix this, others have asked suppliers to work differently — but suppliers won’t change their behavior. Waystation AI doesn’t try to fight this. Instead, we take what’s already flowing and turn it into something procurement teams can seamlessly act on — every quote you’ve ever received, comparable; every document you need for an audit, organized; every certification that’s about to expire, surfaced before it does.
The result: a sourcing team that runs several times the volume without adding headcount.
Energy is the signal
I’m a problem solver at heart, and I love to build things. By early afternoon, it was clear there was a high density of interesting things to tackle that give me energy.
The other thing that stood out was trust. The Chief of Staff role runs on it, and Ryan and I have a massive head start here. That trust comes from years of building together — both celebrating the highs and navigating the lows — and from staying close in the decade since. Ryan is still my most active champion and mentor — he’s someone I have gone to with big questions, personal and professional. He’s always both challenging and supporting me.
At the end of the day, together, Ryan asked me how I thought I’d feel that night when I got home and replayed it.
Energized. Excited.
Sometimes the formula really is that simple: problems worth solving, with people you trust and actually enjoy being in the trenches with.
