Volunteer Sailing Instructor Jobs in Chicago, IL

Description Are you passionate about sailing, coaching, and helping sailors grow. The City of Lake Forest is seeking an energetic Program Supervisor - Assistant Head Sailing Coach to help lead Lake Forest Sailing's community programs, youth racing teams, rentals, regattas, clinics, and special events. This is a rare opportunity in the sailing world: a regular, full-time, year-round City position with a full benefits package, paid time off, and participation in the IMRF pension system.

This is not seasonal or contract coaching work. It is a long-term opportunity for someone who wants to build their career while helping shape the future of sailing in Lake Forest. Lake Forest Sailing is a U.S

Sailing Certified Community Sailing Center focused on growing the sport and helping sailors reach their full potential. The program has a strong relationship with the award-winning Lake Forest High School sailing program, which has a long tradition of competing at the highest level in Midwest scholastic sailing. Sailors represent Lake Forest at regattas throughout the Midwest as part of the Midwest Interscholastic Sailing Association circuit, developing skills in race tactics, boat speed, teamwork, communication, boat handling, and high-level competition.

With coach boats, prams, Optis, ILCAs, 29ers, C420s, small keelboats, and recreational watercraft, Lake Forest Sailing offers a dynamic lakefront environment for someone who loves coaching, thrives on the water, and wants to support sailors in a committed team culture built on camaraderie, sportsmanship, and pride in representing Lake Forest Sailing. Why Join the City of Lake Forest. This is a regular, full-time, year-round City position with a full benefits package, not a seasonal or contract coaching role.

Be part of a recreation team that creates meaningful, active, and welcoming experiences for residents of all ages. Help lead a U.S. Sailing Certified Community Sailing Center that is focused on growing the sport and supporting sailors at every level

Support a strong scholastic sailing tradition through Lake Forest High School's award-winning sailing program and participation in the MISSA circuit. Work in a beautiful lakefront setting with a team that is passionate about sailing excellence, community recreation, and high-quality instruction. Play a leadership role in shaping the future of sailing in Lake Forest while supporting staff development, program expansion, youth racing, community sailing, and waterfront opportunities.

Examples of Duties Assist with planning, coaching, and supervising community sailing programs, youth racing teams, rentals, regattas, clinics, and special events Coach and support race team participants while promoting a positive, safe, competitive, and welcoming sailing environment Support the Lake Forest High School sailing program and youth racing teams through seasonal training, travel, regatta preparation, and race-related logistics Recruit, train, schedule, supervise, and support seasonal sailing staff, dockhands, race coaches, and volunteers Support Sailing Center operations, including equipment, supplies, rentals, facility use, setup, and maintenance coordination Assist with program budgets, purchasing, records, participation tracking, and program evaluation Respond to participant, parent, sailor, and patron questions or concerns in a timely and professional manner Help promote and grow Lake Forest Sailing through community engagement, marketing support, staff development, and program improvement Support citywide and department special events as needed Qualifications High school diploma or GED required; bachelor's degree preferred Experience teaching, coaching, or supporting sailing programs required; previous youth sailing coaching experience strongly preferred U.S. Sailing Level 1 Instructor certification required; Level 2 or Level 3 certification preferred SafeSport certification required, or ability to obtain Additional U.S. Sailing certifications, including Instructor Trainer, Powerboat Instructor, or advanced Keelboat training, preferred Strong communication, leadership, organization, customer service, and problem-solving skills Ability to train, motivate, supervise, and support seasonal staff and volunteers Ability to work effectively with participants, families, staff, community organizations, schools, and other City departments Ability to travel frequently, tow trailers, and work weekends, after-school hours, and seasonal peak periods, especially during the March through November sailing season Valid driver's license required CPR, AED, and First Aid certification required within 90 days of hire and must be maintained Supplemental Information Full Benefits Package Full salary range: $52,061 - $74,675, depending on qualifications Insurance: Medical (PPO/HMO), dental, vision Leave: 13 paid holidays, front-loaded vacation and sick time, parental leave Retirement: IMRF pension, plus 457(b) and Roth options Additional Benefits: Tuition reimbursement, Employee Assistance Program, legal and life coverage, Public Service Loan Forgiveness eligibility, longevity bonuses, and annual merit bonus opportunities based on exceptional performance The City of Lake Forest is an Equal Opportunity Employer

We welcome applicants of all backgrounds and experiences.