Lead Optimist Coach - Full Time

Position Overview & Details

The Davis Island Youth Sailing Foundation (“DIYSF”) Lead Optimist Coach is responsible for leading the development, training, and day-to-day coaching of the DIYSF Optimist Race Team while also supporting and helping guide the Educational sailing programs that serve as the primary pathway into long-term sailor development.

This position is a leadership coaching role focused on building a strong Optimist pipeline from beginner sailors to competitive racers. The Lead Optimist Coach will oversee the Optimist coaching environment, plan and deliver high-quality practices, support assistant coaches and instructors, communicate professionally with families, and help ensure that DIYSF sailors progress through a clear, positive, and developmentally appropriate pathway.

The ideal candidate is an experienced youth sailing coach with strong Optimist knowledge, a development-first mindset, and the ability to work with sailors across a wide range of ages and ability levels, from beginner educational sailors to competitive Optimist racers.

• Supervision 
  • Received: Executive Director and/or Performance Programs Manager
  • Exercised: Assistant Optimist coaches, educational instructors, junior instructors, and volunteers as assigned
• Compensation: Salary, commensurate with experience
• Time Requirements: Full-Time (40+ hours per week)

Key Responsibilities

Optimist Program Leadership

Lead DIYSF’s Optimist pathway, including Green Fleet, and RWB sailors. Set expectations for practice structure, safety, sailor engagement, sportsmanship, and coach professionalism. Coordinate assistant coaches, instructors, junior instructors, and volunteers to ensure consistent instruction and a positive team culture.

Optimist Race Team Coaching

Plan and run organized, age-appropriate practices that include chalk talks, land drills, on-water training, racing scenarios, games, and debriefs. Teach Optimist boat handling, sail trim, body positioning, steering, tacking, gybing, mark roundings, starting, tactics, rules, and racecourse strategy while emphasizing long-term sailor development over short-term results.

Educational Program Support

Support and help guide DIYSF’s Educational sailing programs by reinforcing safe boat handling, confidence, independence, and readiness for continued sailing. Help align Educational curriculum with the Optimist pathway and identify sailors who may be ready for Green Fleet, private lessons, Homeschool Sailing, or other DIYSF development opportunities.

Sailor Development

Track sailor progress, provide individualized feedback, and help sailors set realistic short- and long-term goals. Serve as a positive role model while promoting independence, resilience, accountability, sportsmanship, and a lifelong love of sailing.

Regatta Coaching & Competition Support

Prepare sailors for appropriate local, regional, and travel regattas. Provide on-site coaching, pre-race briefings, on-water observation, post-race debriefs, and constructive performance feedback. Assist with regatta logistics, including equipment preparation, loading, unloading, towing coordination, and family communication.

Safety, Risk Management & Equipment

Maintain and enforce DIYSF safety standards, including PFD use, weather awareness, supervision, emergency procedures, incident reporting, and on-water risk management. Ensure boats, sails, rigging, coach boats, marks, radios, and safety equipment are prepared, maintained, organized, and used responsibly.

Parent & Staff Communication

Communicate clearly and professionally with sailors, parents, coaches, instructors, and staff regarding schedules, expectations, sailor progress, regattas, and program updates. Use DIYSF’s official communication platforms and escalate sensitive concerns to the Executive Director or Performance Programs Manager when appropriate.

Summer Camp & Introductory Program Support

Assist with Summer Sail Camp and other introductory programs as assigned. Help identify sailors who may be ready for educational, Green Fleet, or future Race Team participation, and help families understand the next steps in the DIYSF sailor development pathway.

Qualifications

• US Sailing Smallboat Level 1, 2 or 3 Coaching Certification (or equivalent) is highly desirable.
• Proven experience in race management, including organizing and running regattas at various levels.
• Extensive experience in competitive sailing as both a sailor and a coach. This should be demonstrated by a proven track record of success at the regional, national, or international level. Include specific achievements and levels of competition.
• Familiarity with Optimist racing, Green Fleet development, RWB competition, and youth sailing progression. 
• Strong leadership skills, with the ability to effectively manage and motivate a diverse team of coaches, staff, and volunteers.
• Excellent communication and interpersonal skills, capable of building strong relationships with athletes, parents, coaches, and other stakeholders.
• Exceptional organizational and time-management skills, with the ability to prioritize tasks, manage multiple projects, and meet deadlines.
• Proven ability to develop and implement strategic plans, set goals, and evaluate program effectiveness.
• Strong problem-solving and decision-making skills, with the ability to adapt to changing circumstances and resolve conflicts effectively.
• Proficiency in using data analysis tools and techniques to assess athlete performance and program outcomes.
• Knowledge of current trends and best practices in sailing, coaching, and youth development.
• Current CPR and First Aid certification.
• Must pass a thorough background check.
• Valid driver's license.
• Ability to work a flexible schedule, including weekends and evenings, to accommodate training sessions, regattas, and other events.
• Must be able to lift and move equipment.
• Passion for the sport of sailing and a commitment to fostering a positive and supportive environment for young athletes.
• Ability to serve as a positive role model for youth, demonstrating sportsmanship, integrity, and ethical conduct.
• Strong work ethic, with a high degree of initiative, responsibility, and accountability.
• Ability to work independently and as part of a team.