One of the first graduates of Oakcliff Sailing’s Sapling program, Madeline Gill is a Sail Designer at North Sails in Charleston, South Carolina, an accomplished racer with success in multiple classes, and a fervent advocate for equality in sailing.

“I grew up in Norwalk, Connecticut and started sailing at Cedar Point Yacht Club when I was six, as crew for my dad on a Vanguard 15,” says Madeline. “I have so many fond memories of junior sailing at CPYC. It was the first individual sport I had participated in and I remember that feeling of independence being partially exciting, but also very scary. Sailing on windy days was completely anxiety-inducing for a long time. I would try to hide from my instructors so I wouldn’t have to go out, and I have a vivid memory of crying while learning to trapeze on a 420. The majority of my memories are very happy, though. The environment surrounding the sailing was fun and relaxed, which definitely allowed me to enjoy competition on the water.”

Madeline graduated from the University of Virginia. “The UVa club sailing team was a great fit for me. There were a handful of other sailors who had experience racing and were dedicated to getting good results. We had strong allies in people like Eddie Wolcott and KC Fullmer who played pivotal roles in the team’s growth from a fledgling underdog when I arrived on campus to a strong contender at the college sailing semi-finals the year after I graduated. Fall semester of my senior year, I studied at the University of New South Wales in Sydney. Fortunately, I was able to join their sailing team and represent them at the 2011 Australian University Games. Sailing regularly on Sydney Harbor was great, but definitely made me grateful for the uniquely robust schedule of high-level racing that the Inter-Collegiate Sailing Association continues to offer American college students.”

“When I enrolled as an Oakcliff Sapling, it was a brand-new program that presented the opportunity to sail frequently, learn from prominent sailors, and gain new skills. After four years with the UVa team where I was nearly always teaching, I loved the idea of dropping to the bottom of the totem pole and becoming a sponge. I had less than a clear idea of what the marine industry encompassed and no concept of where I could fit into it. [Oakcliff Executive Director] Dawn Riley has, without doubt, been the primary mentor in my journey to where I am now. Dawn’s presence in my post-grad life showed me that there are infinite paths to achieving success in sailing. One of the strongest values she has instilled in me is the importance of self-awareness and introspection. The environment that Dawn created gave me a feeling of empowerment that I haven’t encountered anywhere else. I felt that I was an equal human capable of achieving whatever I wanted. With the right focus and effort, the sailing industry was my oyster.”

“Working with the Vestas 11th Hour Racing shore crew in Newport as they prepared for one of their first ocean crossings and again in Cape Town between the longest consecutive legs of the Volvo Ocean Race was such a fun experience. I had never appreciated the full extent of prep work that goes into offshore sailing. Helping to provision the boat was a highlight for me. I love cleaning and organizing, so making sure everything was packaged properly and stored in a smart way was fun, though I won’t be sad if I never have to wax another 65-footer again!”

“Moving to Newport in 2014 opened my eyes to another level of competitive sailing. Weeknight racing in PHRF, Shields, J/24, Thistle, and VX One fleets allowed me to both make friends and meet people who eventually helped me get hired by the North Sails Design Department. New York Yacht Club’s premier events for IRC/ORC and one-design racing were always highlights of the summer.”

“I have been with North Sails for over four years now,” says Madeline (pictured with her dog Millie), who lives in Charleston. “I started out mainly working on one-design sails, but have transitioned almost entirely to custom racing and cruising boat sails. Designing sails for boats with inventory limitations and sizing restrictions can be a fun challenge, but finding the right flying shape for a sail that has no confines (other than attachment points) allows for creativity that can be just as rewarding.”

Madeline is passionate about diversifying the sport. “The yacht club nearest to me as I write this has a by-law prohibiting women from even applying for membership,” she explains, “and the America’s Cup has fewer women racing now than it did when I was two years old. I was turned away from the first sailing job I applied for because they had just hired a girl and didn’t think having another on the coaching staff was necessary. I’ve been overlooked by competitive teams because they already had one girl onboard, and the idea of having more than one girl continues to be outlandish in 2022. These experiences, and countless others in the same vein, have both beaten me down and inspired me to do all that is in my power to move the sport forward.”

“My current motivation is this: I owe it to my family, educators, coaches, and mentors to mobilize the strength and initiative they all instilled in me. And I owe it to all the young girls about to step into an Opti for the first time this summer, to make sure that when they grow up there are more than enough meaningful spaces for them in our sport.” ■

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