A woman in white pants and a striped shirt stands on the deck of a yacht, with a helicopter and a red flag against a clear blue sky.

Jenny Chiles

Commercial Director | Fort Lauderdale

“I grew up in Oklahoma, so yachting wasn’t exactly the obvious career path. More than 30 years later, I’m still here, and still loving it.”

– Jenny Chiles, Commercial Director

My Story

I grew up in Oklahoma, which isn't exactly where you'd expect a career in yachting to begin. After I moved 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?" After that, I stayed three years, and that's grown into a career of 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, which has given me a broad view of the industry and some 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 no matter how serious things get, I will always believe that yachting should be fun.

Experience

30+ years in the yachting industry
Leadership experience across brokerage, management, media and commercial operations
Managed global teams and multi-office operations
Extensive experience working with yacht owners, buyers and sellers
Lived and worked throughout the US and Caribbean

Beyond yachting

I was born in Kansas and grew up in Oklahoma in the 70s, which was, in my opinion, an awesome time to grow up. After college, I moved to South Beach, where life was very Miami Vice, before spending months at a time sailing around the Caribbean. I’m still an Oklahoma girl at heart, especially when it comes to basketball, and these days it has to be Oklahoma City Thunder. I’m happiest cooking for friends and family, travelling somewhere new and having people around me. And I’ve pretty much always had a dog in my life. A home doesn’t feel quite right without one.

What industry myth would I most like to retire?

That change is something to fear. Embracing change keeps you on your toes but also helps you to thrive.

What's in my suitcase?

My phone, AirPods, passport and a doorstop. I sleepwalk, so the doorstop is essential!

What do I enjoy most about my role?

Working with the Y.CO team is the best. It’s a genuinely authentic group of people who care about our clients and about one another. That’s very special and unique in our industry.

A woman in white stands on the deck of a luxury yacht in the foreground, with a white helicopter and a yellow banner against a blue sky in the background.
A smiling woman in a striped shirt and sunglasses stands behind a yellow banner on a boat under a clear blue sky.
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.

My Favourite Place

18°29’57”N 64°21’27”W

My Favourite Yachts

The gleaming white superyacht Lunasea glides through calm blue waters under a clear sky.

Lunasea

  • 73 M

  • 12 Guests

  • 2017

Please enquire
The sensational amenities include an 8m infinity pool, a large beach club with sea level terraces, a cinema and wellness centre.
A magnificent three-masted schooner glides across the vast, blue ocean under a sky dotted with fluffy white clouds.

Sea Eagle

  • 81 M

  • 10 Guests

  • 2020

From €550,000  p/w
Epic sailing combines with luxury comfort on board Sea Eagle, a yacht offering a fresh perspective on breathtaking locations.
A majestic white sailboat with a compass rose on its sail glides across the deep blue ocean under a clear sky.

Windrose of Amsterdam

  • 46 M

  • 10 Guests

  • 2002

Please enquire
A beautiful classic schooner with an updated interior, comfortable deck spaces which are ideal for relaxation and a knowledgeable crew.
A sleek green yacht named Pink Shadow cruises on calm blue waters near a lush, mountainous coastline.

Pink Shadow

  • 58 M

  • 12 Guests

  • 2023

From $510,000  p/w
Iconic design and exceptional spaces, including the Tahiti Plage beach club which opens on both sides, set Pink Shadow apart.
A sleek, modern yacht cruises through the deep blue sea under a bright, cloudy sky.

Come Together

  • 60 M

  • 12 Guests

  • 2022

From $490,000  p/w
Come Together's outstanding spaces, including a vast sun deck with jacuzzi and large swim platform, wow guests every time.
A large, sleek sailing yacht with tall masts and sails glides across a calm, blue ocean against a backdrop of a cloudy sky.
Relax in the turquoise waters of this yacht's jacuzzi, surrounded by the stunning blue sea and a rugged coastline.

Aquijo

  • 86 M

  • 12 Guests

  • 2016

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The world’s largest ketch, combining agile handling with an underwater viewing pool for a truly iconic sailing experience.

Moodboards