Happiness Doesn’t Have to be a Heavy Lift
Photo Credit: Matt Chase / The New York Times
CityPickle is your home for pickleball. Find the club nearest to you.
Clinics, open play, leagues, tournaments… We have something for everyone.
We’re excited to share that our Co-Founder and Co-CEO, Mary Cannon, was featured in Where the Boss Got Started, the CEO Diet feature in Bloomberg Businessweek.
Before building CityPickle, Mary’s first role was as a packer for Bekins Moving Co. Long days on the job taught her that work isn’t finished until the team crosses the line together. Once she wrapped her own packing assignments, she jumped in to move boxes alongside everyone else. That early exposure to shared responsibility, attention to detail, and true teamwork has stayed with her and continues to shape how she leads today.
Now that we know where the boss got started, naturally, we had to ask… what were the rest of us doing before this?
General Manager
In high school, my first job was a busser and food runner at my family's restaurant, where I mastered the art of balance (literally carrying full trays of food on my fingertips, and figuratively staying calm under pressure). It gave me a real appreciation for the hospitality industry and the people who make great experiences happen. Later, working at an advertising agency on Ford and Lincoln taught me how to blend business strategy with creativity - something I use every day at CityPickle.
Senior Sales Manager
My favorite summer job was bartending on Block Island right after college. It taught me how to stay calm under pressure, think dynamically, and communicate clearly- skills that have stayed with me ever since. As a bonus, I can still make a top-notch mudslide if the occasion calls for it!
Chief Operating Officer
My favorite summer and weekend job in high school was working as a cocktail server at a catering hall. I somehow became the most emotionally invested staff member, crying happy tears at nearly every wedding as if I were part of the family. Looking back, it was probably less about the open bar and more foreshadowing a full-blown career in hospitality.
Director of Retail
I grew up playing tennis and discovered my competitive spirit around age seven. In high school and college, I spent my summers teaching tennis for my longtime coach and running programs across New Jersey. Those summers also doubled as a crash course in navigation, long before Google Maps, when finding the right court often meant getting lost first. I was responsible for showing up, delivering a good experience, and representing my coach’s program—similar to owning store performance and brand standards today.
Director of F&B Operations
My first job at 16 was at a store that sold floral tablecloths in 23 different sizes, each with its own very specific, non-negotiable folding method that I was expected to have memorized. I became a keyholder within six months, which I'm convinced was less about my leadership potential and more about the fact that I could fold a 60x120 without being asked twice. To this day my linen closet looks like a retail display, and I have Ava, my former boss, to thank, or blame, for that.
Head Chef
My favorite job during college breaks was working for a company that rented bounce houses and slides for kids’ events. Safe to say, I found a better fit, and bring the same pride, precision, and high standards to everything I create at CityPickle.
From packing trucks and bouncing houses to folding tablecloths with suspicious precision, the early days of our team were a mix of trial, error, and skill-building.
All of which add up to a team that knows how to jump in, adapt quickly, and get things done without taking ourselves too seriously.
Interested in joining the team? Check out open positions here.
Photo Credit: Matt Chase / The New York Times
An accomplished sales and marketing executive with deep experience in partnership development, Anna will be an immediate asset to the CityPickle...
Official paddles of our team. And maybe your next go-to on the court.