Reports To: Caitlyn Ridgley, Adult Program Director
Status: Full Time
Description Last Updated: August 15, 2025
Courageous Sailing
Courageous Sailing is a nonprofit community sailing and youth development organization committed to providing people of all ages and backgrounds with opportunities to learn, sail, and enjoy the waterfront. We work at two locations in Boston: the Charlestown Navy Yard on Boston Harbor, and Jamaica Pond. Our mission is to transform lives through sailing programs that inspire learning, personal growth, and leadership.
Position Overview
We are looking for an Adult Program Manager to help guide and support our members, students and staff. Our Adult Program Manager is often the first member of our leadership team that our members and students interact with before ever arriving on site, welcoming them to our community and helping them meet their individual sailing goals.
The Adult Program Manager assists the Adult Program Director (APD) in planning, managing, and implementing all adult programming, including the supervision of 30-40 seasonal staff. Their primary focus is to manage and grow a large sailing program while maintaining the highest standards of safety and quality–attracting and cultivating a strong base of members and students, and developing the robust staff needed to consistently deliver a high-quality sailing program.
Schedule
In season (May-Oct), this position is expected to work weekend days and/or evenings with regularity. During our off-season, the schedule will largely shift to normal business hours M-F, with some Saturdays required to support the racing program. When weekend days are worked, we will aim to shift the schedule so that the employee will have two concurrent days off later in the week.
Responsibilities
Adult Program Officer in Charge (20%)
- Manage the Charlestown site and serve as Officer in Charge regularly on weekdays during AP shifts and one weekend day per week unless otherwise scheduled.
- Prioritize and promote the highest standards of safety and risk-management.
- Model safe, respectful, and responsible behavior to participants and peers at all times.
Member and Student Communication and Engagement (25%)
- Respond to member and student questions; guide and support them in their sailing education and opportunities; ensure highest-possible levels of customer satisfaction, engagement and retention.
Staff Development (30%)
- Staff Recruitment – recruit potential new staff both through online platforms and in-person opportunities through yacht clubs and colleges\career fairs, etc.
- Staff Retention – retain/rehire current and former staff; work to keep them positively engaged, motivated and satisfied with their jobs.
- Staff training – create and implement a training plan and schedule for on-water sailing and staff that will
- Help staff to understand and meet expectations, including the skills and certifications they will need for different roles.
- Support staff with the opportunities to develop, practice and refine those skills.
- Create pathways for staff to work cross-programmatically, grow in their roles, and advance into new ones
- Staff Scheduling – oversee the scheduling process while maintaining clear communications/expectations with staff and ensuring that staffing shifts are filled.
- Create or review and revise curriculum and lesson plans for existing and new programs. Train staff on core objectives and standard practices to ensure a consistent educational experience for all students.
Program Planning and Communications (25%)
- Partner with APD to set annual Adult Program (AP) goals and expectations
- Support the APD in marketing and and fulfilling AP memberships, course offerings; and group events; Work with APD to meet or exceed revenue targets while ensuring program expenses remain within budget.
- With the APD, update and disseminate AP member/student manuals or information resources, detailing what members/students can expect from Courageous, and what we expect from them.
- Participate in strategic and operational planning for Courageous Sailing as a whole.
Qualifications
At Courageous Sailing, 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 you have a less traditional background. We are looking for applicants with the following qualifications:
- Strong sailing/racing instruction skills and experience required
- Program management experience strongly preferred
- Degree from four-year college or university and or equivalent combination of education and experience preferred
- Experience with scheduling preferred
- Committed to cultivating a kind, diverse, equitable, and inclusive community
- Must be highly detail oriented and organized with the ability to manage multiple concurrent projects and initiatives
- Strong judgement, situational awareness, and analytical skills
- Excellent written and verbal communication skills
- Comfortable giving and receiving feedback and resolving disputes
Certifications
- CPR / First Aid / AED
- Preferred: US Sailing Basic Keelboat Instructor
Compensation
The pay range for this position is $55,000-$60,000, depending on experience and relevant certifications.
To apply, go to https://courageoussailing.org/employment-application/
*Flexible Start Date