Greg Gaillard

Senior marine industry executive and licensed U.S. Coast Guard Master with extensive experience in yacht brokerage, operations leadership, training & development, and customer experience. Proven leader with a track record of building teams, launching new locations, driving sales, and managing complex multi-site operations. PROFESSIONAL EXPERIENCE Yacht Broker – Oyster Harbors Marine (2024 – Present) • Sell and represent premium yacht brands including Viking, Valhalla, Mag Bay, Everglades, and Princess. • Launched and manage a new Milford, CT location at Dockside Brewery, overseeing six slips of new and brokerage vessels. • Advise clients through purchase, negotiation, sea trial, survey, and delivery. Director of Training & Development – Barton & Gray Mariners Club (2018 – 2025) • Hired, trained, and professionally developed over 300 captains and employees nationwide. • Designed and implemented comprehensive training programs across all divisions. • Led onboarding, leadership development, and compliance training; managed training budgets. General Manager – Freedom Boat Club (2016 – 2019) • Directed all sales and operations for six Connecticut locations. • Oversaw dock staff, fleet logistics, on-water training, and new boat deliveries. • Built strategic partnerships with Brewer Yards, Mystic Shipyard, and regional vendors. • Led member events and represented the brand at regional boat shows. Regional Sales Executive – POP Yachts (2015) • Managed vessel listings, buyer inquiries, showings, negotiations, surveys, and deliveries. • Created high-quality MLS advertisements and coordinated seller communications. Educational Leader – Suffield & Derby High Schools (2001 – 2014) • Progressed from teacher to Athletic Director, Assistant Principal, and High School Principal. • Led school operations including budgeting, staffing, evaluations, scheduling, and compliance. • Awarded $500,000 state grant to design and implement a high school redesign focused on personalized learning.

Captain Gregory A. Gaillard
Milford, Connecticut | 860-655-2033 | greggaillard1414@gmail.com
PROFESSIONAL SUMMARY
Senior marine industry executive and licensed U.S. Coast Guard Master with extensive experience in yacht
brokerage, operations leadership, training & development, and customer experience. Proven leader with a track
record of building teams, launching new locations, driving sales, and managing complex multi-site operations.
PROFESSIONAL EXPERIENCE
Yacht Broker – Oyster Harbors Marine (2024 – Present)
• Sell and represent premium yacht brands including Viking, Valhalla, Mag Bay, Everglades, and Princess.
• Launched and manage a new Milford, CT location at Dockside Brewery, overseeing six slips of new and
brokerage vessels.
• Advise clients through purchase, negotiation, sea trial, survey, and delivery.
Director of Training & Development – Barton & Gray Mariners Club (2018 – 2025)
• Hired, trained, and professionally developed over 300 captains and employees nationwide.
• Designed and implemented comprehensive training programs across all divisions.
• Led onboarding, leadership development, and compliance training; managed training budgets.
General Manager – Freedom Boat Club (2016 – 2019)
• Directed all sales and operations for six Connecticut locations.
• Oversaw dock staff, fleet logistics, on-water training, and new boat deliveries.
• Built strategic partnerships with Brewer Yards, Mystic Shipyard, and regional vendors.
• Led member events and represented the brand at regional boat shows.
Regional Sales Executive – POP Yachts (2015)
• Managed vessel listings, buyer inquiries, showings, negotiations, surveys, and deliveries.
• Created high-quality MLS advertisements and coordinated seller communications.
Educational Leader – Suffield & Derby High Schools (2001 – 2014)
• Progressed from teacher to Athletic Director, Assistant Principal, and High School Principal.
• Led school operations including budgeting, staffing, evaluations, scheduling, and compliance.
• Awarded $500,000 state grant to design and implement a high school redesign focused on personalized
learning.
EDUCATION & CREDENTIALS
• U.S. Coast Guard Master 50-Ton Captain License – The Nautical School (2017)
• Sixth Year Degree, School Administration – Sacred Heart University (2009)
• Master of Education, School Principal – Westfield State University (2006)
• Bachelor of Arts, Social Science – Keene State College (2001)

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