The owner of Longshore Sailing School in Westport, Connecticut, an accomplished sailing educator and the recipient of two prestigious US Sailing awards, Jane Pimentel loves her work…and “her people.”
“I’m originally from Dartmouth, Massachusetts and now live in Wilton, Connecticut with my partner Benjamin and dog Grady…yes, named after Grady-White Boats,” says Jane. “I learned to sail at Community Boating Center and also at Sea Lab, both in New Bedford. Most of my ‘learn to sail’ was on Catalina 14.2s and Laser Picos before moving on to C420s and Sonars.”
“I sailed at Tabor Academy, but had to put competitive small boat sailing on hold due to numerous ankle surgeries. I’ll never forget sitting in an auditorium in the academic building, preparing to take my Racing Rules test. I’m fairly certain I was more nervous about that exam than the SAT!”
“I was lucky enough to go to college on the West Coast of Florida and stay in a property my family had in Sarasota. I much preferred being outside of a classroom working, instead of inside studying something I thought I’d never need. Between classes I searched online for boating-related positions in the area, as I was seeking a way to justify cutting back my course load. I figured as long as I was being productive, my parents couldn’t possibly care what I was doing!”
“I saw a listing for an instructor position at Sarasota Youth Sailing Program. They were starting a new weekend learn-to-sail course, and were looking for someone to create and lead the new venture. I was given kids, Optis, powerboats and two volunteers to assist me. It was the first time I was on my own to create and implement curriculum and lesson plans – I was sold.”
“Weekends were my world at SYSP. They’d sometimes call me to lend a hand with Red, White and Blue Optis, Lasers or 420s, and I’d say ‘yes’ to any opportunity. Venice Youth Boating Association was looking for a new coach, which required weekdays and weekends. I worked for both programs for a bit, but ended up focusing on VYBA’s Opti program. It was eye opening to see the ‘Opti scene’ on the Gulf versus Buzzards Bay. Culture shock for sure! Events were laid back, and I had full rein of my team without parental interference. This is where I started to become more confident in my coaching skills as well as my ability to manage a fleet, team members, travel, and sailor/parent expectations.”
“I first time I knew I would make sailing my career was the day after I finished my US Sailing Instructor Trainer course, taught by Kim Hapgood and Guy Fleming. At the time I was the youngest Instructor Trainer US Sailing ever had, and I certainly felt the honor and also the burden of that. After spending time with Kim throughout the course and during US Sailing’s National Sailing Programs Symposium, I realized I too could make sailing education the focus of my life.”
“I’ve had the luck and privilege to create bonds with many incredible women through sailing education. I have three in my life that are Sailing Directors and the Head Coach of a college team: Jessica Koenig, Brianna Grenier and Tara Foster, respectively. I’d be remiss if I didn’t share their names, as we mentor each other on a regular basis. We’ve chosen this ‘odd’ life, and having people who can guide you but also relate to you on so many levels is a gift. While it’s definitely not a ‘girls only’ club, there’s something about thoughtful, kind and intelligent women always being in your corner that’s so meaningful in an industry where being female and under 50 may be seen as a detriment to one’s success.”
“It’s not just about the ladies, though. Peter Durant was the Executive Director at Community Boating Center when I was hired as a sailing instructor for the first time, in 2006. As a strong willed – albeit stubborn – teen, I watched how Peter interacted with the staff, truly listening to their struggles, providing constructive feedback, and helping build ‘game plans’ in the most nonjudgemental way. I know I pushed boundaries, always having good intentions. Peter had the most graceful way of keeping me ‘in line’ while fostering my want for more responsibility, more say in what my duties were…more of everything!”
“I spent fifteen seasons as a student, instructor and manager at CBC, working my way up from Junior Instructor, Instructor and Head Instructor to Program Manager. I knew it was an opportunity for me to push myself and create space for myself within the organization. I spent a lot of time working on outreach, making contacts with housing authorities, school administrators, and teachers. I was working outside my comfort zone, and absolutely loving it.”
“When Peter departed CBC, I claimed a specific chair that
was in his office. That chair was where I literally laughed and cried, planned lessons for the first time, and sat just minutes after I performed CPR on the father of two of my junior students. Peter and I had been through a lot together. He taught me how to foster a collaborative work environment, to lift everyone around me up, and to be a leader without being a ‘boss.’ Without Peter allowing me the freedom to work within set boundaries, while pushing said boundaries, I most certainly would not have made sailing education my career.”
“I was responsible for fleet maintenance, program registration, program creation, implementation of US Sailing’s REACH program, US Powerboating’s Safe Powerboat Handling courses, and hiring, training and managing staff for CBC’s two locations. I also created a pipeline for CBC’s sailors to have opportunities to travel to local regattas. Leaving CBC was what was best for my professional and personal growth, but I still get a pang in my heart when I’m in town and drive by Clark’s Cove, where I learned to sail.”
“In April 2014, I was hired by Longshore Sailing School as General Manager at their satellite location in Greenwich. I was GM for three seasons, while also assisting with the Westport location’s off-season responsibilities. When the former owner initially asked if I was interested in taking over the company, in 2015, I immediately said no. In my mind, I had not been there long enough to make an educated choice. The next year I was asked the same question. This time, my answer changed. I’d made a home in Connecticut, with my family only three hours away. I knew I wanted sailing education to be in my life forever, and this was a sure way of making that happen.”
“Longshore Sailing School has a staff of forty-five people, two of whom work year-round. About 50% of our instructional staff come from other programs along Long Island Sound; the other half are ‘homegrown.’ Our staff ranges in age from 16 to 82. We currently have twenty-nine instructors, nine beach/dock hands, five office clerks, one general manager and one business manager. When interviewing staff, they often ask why I like working at LSS. My answer is always the same: I love the people. Our staff are what make LSS great. I strive to cultivate and maintain a positive workplace culture where it’s OK to ask for help, and where learning from mistakes makes us a stronger unit.”
“While Longshore doesn’t have a traditional scholarship program, I do set aside classes for those that may not be able to otherwise afford them. We don’t have a formal application process, as I choose to believe that those requesting help with providing a safe summer for their child truly need the support. Families sometimes ask for help, but I personally reach out to the majority of them through online parent groups. I post an offer welcoming people to contact me directly if they’re in need of programs for their children. We do our best to make programming as accessible as possible. As of last month, we’ve given the value of $25,000 of programming to those in need. We have never been asked about this before, so this is the first time we’ve put a dollar value to programs ‘gifted.’”
“The Longshore Sailing School family is what keeps me motivated each season. I look forward to their spring return and dread their fall departure. Our staff retention rate is pretty great. Being able to watch someone’s personal growth from age 16 to 22 is both a nightmare and a privilege. I have a former staff member that went to grad school in Italy. He came back to LSS on his visit home just to check on me. Another brought his girlfriend to meet me, then she became his fiancee and now I’ll be going to their wedding in October. Many staffers have told me that they have deferred the ‘real world’ or came back to have ‘one more year’ because of their love for the school and for me. I will never take their love, support, and blood (oyster shells), sweat (gross, humid days) and tears (laughing until you cry) for granted.”
“I’ve been honored to receive two US Sailing awards. The first was in 2012 when I received the ‘Excellence in Instruction’ award. I was shocked that someone thought to nominate me, and even more shocked when I received the email stating that I’d been chosen. This was a huge milestone for me, as the award was presented the same week I became an Instructor Trainer. Three former recipients were my instructors at Community Boating Center, so I felt I did them proud.”
“This year, I was honored with the Virginia Long Sail Training Service and Support Award. I was at a loss for words when I was told I’d be receiving this award, and for those that know me, words are something I always have. Part of the description of the award is “support excellence and safety in sailing instruction and/or programs.” I take my role in sailing education very seriously. While I have my own facility, staff and students to be concerned with, I also have the 188 sailing instructors
from 2023 and ’24 that came through my Instructor Certification courses plus their students on my mind. I do not take the responsibility of teaching, evaluating and certifying sailing educators lightly. While sailing may be looked at as ‘just a sport,’ it’s a place where people learn to build trust, exercise both physically and mentally, make friends for life, and have a sense of freedom I’ve yet to find elsewhere. To top it all off, to have Kim Hapgood presenting ‘The Ginny’ to me with my biggest supporters in the room, I could not have asked for anything more fulfilling.”
“When not ‘in season’ or doing what I call being a ‘fun facilitator,’ I’m often driving Route 95 from my house to Dartmouth to visit my parents, my family and the two greatest humans, my niece Rhea and nephew Cooper.”
“While I’m not a cruiser, I am a traveler. My travels just happen to bring me to the water quite often. My absolute favorite place to sail is on the southern coast of Ilha de São Miguel, Açores, Portugal. My father is from the Açores, and my favorite place to visit is the small village of Ribeira Quente. I was able to form a relationship with a small sailing program named Clube Naval da Povoação. I’ve led fundraising efforts for their program, helped with coaching, and had the pleasure of sailing with their students. The biggest waves and wind I’ve ever sailed in was this past March, in an ILCA 6 below the cliffs of Povoação. It’s an incredible location. The best thing about sailing has nothing to do with sailing. The best thing is the people you meet.” ■
