Assistant On-the-Water Director (Youth Sailing)

Columbia Sailing School/Columbia Yacht Club
111 N Lake Shore Dr Chicago
Chicago, IL 60601
United States

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

Job Description

Position: Assistant On-the-Water Director (Youth Sailing)

Supervisor (Reporting To): On-the-Water Director

Job Summary:

The Columbia Sailing School's Assistant On-the-Water Director plays a crucial role in the overall success of our youth programs. Managing and overseeing operations of the Sailing School, including fleet management, youth program operations, communications, volunteer coordination, programming, budgeting, and marketing, they ensure the smooth functioning and growth of our sailing initiatives. Collaborating closely with the On-the-Water Director and Assistant On-the-Water Director (Adult Sailing) on all school activities to foster a cohesive and dynamic learning environment for our students. With a dedicated and certified staff, the Director ensures safety, fun, and effective learning experiences for our students. Additionally, they actively participate in coaching during high school and middle school seasons, as well as coordinate and assist with regattas. This position entails a year-round commitment, with occasional national, regional and local travel. The Assistant On-the-Water Directors contributions extend year-round as they engage in shaping the future of our youth sailing programs.

Principal Duties and Responsibilities:

  • Directly manage all programs in compliance with the On Water Director’s guidelines.
  • Develop and execute a year-round marine education program following US Sailing’s program and Stem/REACH Program guidelines.
  • Recruit, hire, and supervise seasonal staff.
  • Provide ongoing training and education for staff throughout the year.
  • Set up and maintain student registrations for all sailing programs.
  • Coach during high school and middle school seasons.
  • Collaborate with the On the Water Director to oversee, register, and inventory all School assets, coordinate maintenance schedules.
  • Uphold best practice safety standards for all Sailing School programs.
  • Assist with regattas and adult coaching as required.
  • Occasional regional and overnight travel to regattas.
  • Lead racing programs for members and students.
  • Ensure updated registrations for all club assets.
  • Perform fleet repairs, including fiberglassing and basic engine repair of sail and power fleet.
  • Coordinate more extensive repairs and maintenance with local vendors.


  • Organize external recruiting activities with a focus on sailing education, race committee, and regattas for all levels.
  • Create high-quality marketing materials for direct distribution.
  • Identify suitable opportunities to promote the Club, including membership and facility rentals.
  • Continuously identify opportunities to enhance the experience for members and potential members.
  • Develop sponsorships and cross-promotions to promote the brand with an emphasis on educational events.
  • Communications:
  • Ensure consistency in all internal and external communications.
  • Promote all educational events in a professional and timely manner.
  • Manage Columbia’s online presence for on-water programs, including website updates and social media communications.
  • Provide requested reports and data to the General Manager, Committee Heads, and Board of Directors.
  • Make recommendations and collaborate with the Board of Directors to establish financial goals for the Sailing School.
  • Attend/participate in daily staff meetings, weekly manager meetings, and committee meetings as required.

Essential Qualifications (Minimum):

  • At least 4 years of coaching experience required.
  • At least 1 year managing a youth sailing school required.
  • US Sailing certifications for Level 1 Small Boat Instructor.
  • CPR/First Aid certification.
  • SafeSport certification.
  • Satisfactory completion of a background check is required.

Application Instructions

If interested, please email with “Assistant On-the-Water Director” in the subject line attaching a resume and cover letter.

At Columbia Sailing School, our highest priority is finding the best candidate for the job. Research has shown that people of color and women are less likely to apply for jobs if they don't believe they meet every one of the qualifications described in a job description. We encourage you to apply, even if you don't believe you meet every one of our described qualifications or have a less traditional background.

About Columbia Sailing School

Columbia Sailing School, a distinguished 501(c)(3) nonprofit organization, boasts an exceptional location on the picturesque docks of the Columbia Yacht Club, nestled alongside Randolph Street on the shores of Lake Michigan. With an unwavering commitment to safety, enjoyment, and education, our seasoned coaches provide a nurturing environment for children to embark on a sailing journey, starting with introductory summer camps and progressing to elite racing teams. The invaluable skills and enduring friendships forged by our youth alumni pave the way for further achievements in high school, college, and even international competitions. For adults eager to embrace the art of sailing, our comprehensive programs cater to both novices and intermediates and are conducted aboard our Colgate 26 sailboats. Our accomplished team of instructors, comprised of both experienced volunteers and certified US Sailing professionals, guide participants through the intricacies of sailing and racing.

Kurt Thomsen
111 N Lake Shore Dr Chicago
Chicago IL 60601
United States
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