Chicago Yacht Club Sailing School Director

Chicago Yacht Club
Chicago Yacht Club 300 W. Belmont Ave.
Chicago, IL 60653
United States

Sailing Management
Manages Others
Experience Required
Housing Provided
Employment Type
Full Time
Work Schedule
Some Travel

Job Description

The Chicago Yacht Club’s Sailing School is currently on the lookout for a dedicated Full-Time Sailing School Director. As we approach our 150th anniversary in 2025, we continue to offer a wide array of 10 distinct summer classes designed to cater to children aged 7-18, ranging from sailing novices to advanced race teams.

The Chicago Yacht Club takes pride in its rich heritage as the city’s foremost sailing destination. It has been the launchpad for numerous esteemed sailors, including Olympians, top match racers, and College All-Americans. The Chicago Yacht Club is also recognized on the Platinum Clubs of America list, a testament to our commitment to excellence in the private club sector.


We invite you to be a part of an environment that nurtures young sailors’ passion for the sport. We expect our director to be enthusiastic, motivated, and ready to share their knowledge and passion with our students and their families.




  1. Program Development: Develop and implement comprehensive sailing/boating programs for all age groups and skill levels. Develop a curriculum and implement four seasons of sailing/boating, which would include training clinics in suitable climates for winter sailing. Work with the Chicago Yacht Club Foundation to further their mission of bringing sailing/boating to youths from underrepresented communities.
  2. Coaching: Assist and provide coaching for both double-handed and single-handed coaching during the fall and spring sailing programs, as well as high school practice and regattas throughout those academic semesters.
  3. Staff Management: Support the General Manager and the On the Water Director in hiring, training, and supervising program managers, sailing instructors, and other staff members.
  4. Safety Compliance: Ensure all activities comply with safety regulations and standards (US Coast Guard/US Sailing). Maintain safety equipment and conduct regular safety drills.
  5. Budget Management: Assist the On the Water Director in managing the school’s budget, including forecasting and financial reporting. Support the Controller during the budgeting process.
  6. Customer Service: Address inquiries and concerns from students and parents promptly and professionally.
  7. Equipment Maintenance: Work in conjunction with Bosun for maintenance and repair of sailing, powerboat, equipment, and sailing school facilities.
  8. Marketing and Promotion: Work with the Communications Department to promote the school and its programs through various channels including social media, community events, and partnerships.



  1. Experience: Previous experience in sailing instruction and program management is required.
  2. Certification: Certification from a recognized sailing association is preferred such as: US Sailing Small Boat Level 1 preferred Level 3 or international equivalent
    SafeSport, CPR and First Aid, NASBLA Safe Powerboat Handling or equivalent
  3. Skills: Strong leadership, communication, and organizational skills.
  4. Physical Requirements: Must be physically fit and able to participate in sailing activities.
  5. Availability: Must be available to work weekends, holidays, and during peak sailing season.


As a salaried Chicago Yacht Club team member, you will be eligible to participate in our comprehensive medical plan, with access to dental and vision care, supplemental life insurance, short-term disability insurance, and other club programs. After one year of service, you will also be eligible to contribute to our 401k retirement fund, which includes a matching contribution from the club.

Please submit a resume and cover letter to be considered for this position.  Materials should be submitted via e-mail and be addressed to:

Applications will be accepted on a rolling basis.  Please apply no later than March 1, 2023, to receive full consideration.

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