Exploring new opportunities · St. Petersburg, FL
Where I've built
About
I lead customer operations teams — support, onboarding, escalations — in SaaS companies that are growing faster than their playbooks can keep up. I started at HubSpot in 2011 as employee #92, stayed eight years, and helped scale the support org from a single room in Cambridge into a global function.
Since then I've worked across the stack: independent consulting for early-stage teams, leading customer support at Tapcheck, and building onboarding and operations programs at Deel. The through-line is the same — translate messy customer reality into operations that are calm, fast, and humane. Cut the noise. Find the signal. Build the team that can run it.
My management style comes from a simple belief: people grow when they're seen. I coach, I mentor, I write the action plan with you. The recommendations on this site aren't quotes I picked because they sound nice — they're from people whose careers I had the privilege to be part of, and that's the work I want to keep doing.
I moved from Boston to St. Petersburg in 2019, which is why my Slack status often involves a sailboat. More on that further down.
Selected work
One of the first 100 employees. Eight years, multiple roles, watched headcount grow more than 50x and the support org grow with it. Managed customer-facing teams through dozens of org changes, mentored ICs into managers, and stayed in the manager seat longer than almost anyone in the function.
Took over a queue-driven support function and rewired it around root cause, self-service, and quality. The numbers moved with the culture.
Built repeatable implementation motion for new customers and led root-cause work on the gnarliest customer escalations — aligning product, engineering, and CX on what actually has to change. Less "fix the ticket," more "fix the system."
DoodleDo
Mobile app
A field guide for new pet owners — built after bringing home my first dog and realizing the onboarding experience for humans-with-puppies was missing.
stpeteortampa
Web
A practical guide for Northeast transplants weighing St. Pete against Tampa. Less SEO bait, more "here's what your weekend actually looks like."
What people say
“Cait was instrumental to the career growth of countless employees. She was one of the most tenured Support managers at HubSpot, and led her teams through company growth and dozens of organizational changes. Cait builds strong relationships with her reports, putting her people first and being deeply committed to their success and growth.”
“Cait provides a working environment that is productive, fun, and motivating, all at the same time. She finds a way to promote and recognize individual contributors creatively and thoughtfully… Cait has an uncanny ability to support her peers and mentees, and she has my highest recommendation.”
“I reported to Cait for nearly two years and she has been one of the most influential leaders I've worked with in my career. Cait will not only listen to your feedback, but will actively help you work on your skill set and put together an action plan to address whatever concerns you may face.”
“Cait was instrumental in helping me grow a career pivot from sales to more technical roles in support and product at HubSpot. She took me under her wing and helped me develop projects to target pain points the team I was looking to join was experiencing. She could brilliantly layer in sports analogies that would hit her teaching points home.”
“I really was thankful that Cait helped coach me when I was applying for a promotion outside of our department. With her networking advice, help with mock interviews, and overall support, I got the job!”
Off the clock
I moved to St. Petersburg for the water and stayed for the sailing. Most weekends you'll find me on the boat, on the courts, or yelling at a Boston or Tampa Bay sports broadcast. Lennon — a Labradoodle, professional supervisor — is usually nearby.
Resume
Contact
I'm open to Support Manager, Client Support Manager, Onboarding Manager, Escalations Manager, and Customer Experience leadership roles.
