Madeline Gill: Grads doing great

Published on March 17th, 2022

As Executive Director of Oakcliff Sailing, Dawn Riley knows a thing or two about burning a path, and while Scuttlebutt Sailing Club boasts about Madeline Gill representing the burgee, Riley stakes an earlier claim in this trailblazer.

The Sapling program is Oakcliff Sailing’s offering for sailors who are considering sailing as a career, and Riley gives this shout-out to one of her protégés from the training center:


Madeline Gill was one of Oakcliff’s first graduates, back when the bunk house didn’t even exist, 10 years ago. She was also the only female Sapling that year. “I actually didn’t think about it much at the time, though, because Dawn and the team did such a good job of treating us all equally. I felt that the expectations of me and opportunities given to me were the same as for all of the guys.”

Oakcliff opened her eyes to the breadth of careers in the marine industry. “I had never considered sailing to be something I could carry more than peripherally into my adulthood until then… I would say that my Oakcliff experience has been foundational to my current life.”

Madeline believes strongly in maintaining a diverse skill set, which is clear, looking at her recent sailing accomplishments: Winning the 2019 VX One North American Championship as spinnaker trimmer, getting 2nd at the 2021 US Women’s Match Race Championship as main trimmer and tactician on a J22, competing in the Newport Bermuda Race on a modified Tripp 41, winning the 2019 Camden Classics cup and Vineyard Cup on a Sparkman & Stephens 53 built in 1935, among many others.

Madeline currently works as a sail designer. “I am really enjoying my current job as a sail designer at North Sails. My primary career goal is to grow within that role. In terms of sailing, I hope to continue gaining experience on boats of all sizes and across multiple disciplines. More specifically, I would love to have any role within a grand prix or America’s Cup team.”

Perhaps what stands out most about Madeline is her passion for diversifying the sport in a meaningful and sustainable way. “I believe that true gender equality will only be achieved when women are adequately represented not only as active crew members onboard race boats, but also as naval architects, rig engineers, sail designers, riggers, boat captains, shore crew members, coaches, performance analysts, race officers, rules administrators, etc.

“If the boats aren’t designed with us in mind and the rules aren’t written with us in mind, we will never have equal representation on the race course.”

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