Jenny Chiles

My Story

I grew up in Oklahoma, which isn’t exactly where you’d expect a career in yachting to begin. After moving to South Beach, a friend asked me to answer the phones for a day at a yacht brokerage. I remember thinking, “What’s a yacht brokerage?” I stayed for three years, and it turned into a career that’s now lasted more than 30.

Early in my career, I was involved in several iconic new-build projects at a time when brokers, shipyards and designers were all learning new digital systems together. Since then, I’ve worked across brokerage, yacht management, media and commercial leadership. It’s given me a broad view of the industry and helped me build wonderful relationships along the way. After this long in yachting, I usually know who to call when something needs to get done.

Today, as Commercial Director at Y.CO, I work closely with our Yacht Sales, Charter Retail and Charter Management teams on growth, revenue strategy and keeping the wheels turning.

I love the commercial side of the business, solving problems and working with people. And however serious things get, I still think yachting should be fun

Beyond yachting

I was born in Kansas and spent my childhood in Oklahoma in the 70s. It was, in my opinion, an awesome time to grow up - the music, the freedom, all of it. Summers were spent on the family farm, with plenty of road trips and ski trips too.

After college, I moved to South Beach. In the 80s, working in a well-known nightclub restaurant, life looked very different from Oklahoma. It was very Miami Vice. Not long afterwards, I started spending months at a time sailing around the Caribbean. The BVIs are still one of my favourite places in the world.

I’m still attached to Oklahoma, particularly when it comes to basketball. For years I was a Lakers fan, but these days it has to be Oklahoma City Thunder. Home wins eventually.

Mostly, I’m happiest cooking for friends and family, travelling somewhere new and having people around me. I’ve pretty much always had a dog in my life too. A home doesn’t feel quite right without one.

What has experience changed my mind about?

I’ve learned to step back and look at the bigger picture. And to remember that, however complex things get, yachting is supposed to be fun.

What's my hidden talent?

I'm double-jointed in both my hips and fingers. I'm also an intensely competitive backgammon player.

What's one thing still on my bucket list?

Hawaii. Once I get there, I’ll have visited all 50 US states.