Youth Program and Outreach Director

Courageous Sailing, Inc.
197 8th Street
Boston, MA 02129
United States

Job Start Date
Manages Others
Experience Required
Degree Required
Security Clearance Required
Housing Provided
From $55,000 To $70,000
Per Year    
Employment Type
Full Time
Work Schedule
No Travel

Job Description
Position Overview:
Courageous Sailing transforms lives through sailing programs that inspire learning, personal growth, and leadership. Since our inception as a 501(c)(3) nonprofit in 1987, our programs have utilized sailing and the marine environment as platforms for social-emotional development and out-of-school-time learning. We are committed to making sailing accessible to metro Boston youth from all walks of life, and we hold true to our founder’s conviction that “Every child’s perspective is improved fifty yards offshore.”

The Youth Program and Outreach Director position reports to the Operations Director, works closely with the Operations Coordinator, and supervises (directly or indirectly) approximately 70 seasonal staff. They are responsible for the planning and implementation of all youth programming and outreach. They are focused on supporting Courageous youth and safely/effectively delivering the Courageous mission to a diverse and inclusive community of families; on building and leading the team needed to make that possible; and on cultivating a safe, engaging, and respectful culture.

Courageous Sailing Leadership Team Qualities:

Courageous strives to be a workplace where employees of all identities and backgrounds can thrive in any role or position. When assessing candidates to join our organization, we are not looking for someone who is "perfect" but someone who will be an ideal team member that is also excited about the Courageous mission. Ideal Leadership Team member qualities include but are not limited to:
  • Ability to participate in and contribute to a safe, engaging, and respectful work environment

  • Ability to promote safety by exercising sound judgement and decision-making and able to assess and mitigate foreseeable hazards

  • Ability to promote respect by cultivating a kind and inclusive community and assisting with supporting and ensuring everyone can be successful

  • Ability to promote engagement by helping to create systems that clearly articulate expectations and empower our staff, students, and patrons

Youth Program and Outreach Director Responsibilities:

Outreach and Social Emotional Learning:

  • Guide organizational efforts to effectively reach and serve Courageous kids and families from low-income and marginalized backgrounds; continue to assess community needs and adapt programs where necessary

  • Build and maintain supportive relationships with students and families

  • Partner with Boston Public Schools to recruit and support students vulnerable to of summer learning loss for our Swim Sail Science program

  • Support students’ transitions and progress through our Swim Sail Science, Steps To Lead, and Instructor-in-Training programs

  • Be a behavior management support and resource for staff; train staff to work effectively with children, manage behavior and support their social-emotional growth

  • Continue to implement diversity and inclusion best practices within all programming

Planning & Implementation:

  • Participate in strategic and operational planning for Courageous Sailing as a whole

  • Set annual youth program goals and expectations

  • Assemble annual youth program budget for board approval and grants

  • Plan and schedule all youth program course offerings in alignment with annual budget and goals

  • Ensure program spending within budget

  • Plan and coordinate program registration process

  • Lead youth program curriculum development, in-season implementation and off-season refinements

  • Respond to parent and community requests and concerns

  • Oversee youth program events, promotional materials, website and calls; maintain up-to-date youth program content on website and social media

Hiring, Training and Staff Development:

  • Recruit, hire and supervise 60-70 seasonal sailing instructors, supervisors, educators, and other program staff, consistent with staffing guidelines

  • Promote staff culture consistent with the values of the program: continuing education, teamwork, mentorship and modeling of positive life skills

To apply, please send a thoughtful cover letter and resume to

Job Requirements
-Degree from four-year college or university and five years related experience or equivalent combination of education and experience preferred
-Enthusiasm and passion for the mission of Courageous
-Must be detail orientated and organized with the ability to manage multiple, concurrent projects and initiatives
-Strong personnel management skills
-Strong analytical skills
-Excellent written and verbal communication skills
-Comfortable giving and receiving feedback and resolving disputes
-Advanced Microsoft Office skills
-Strong desire to provide equitable access to education and enrichment is a must
-Prior teaching experience preferred
-Prior experience working with marginalized populations preferred
-Sailing experience preferred but not required
Ashton Wollett
197 8th Street
Boston MA 02129
United States
Courageous Sailing, Inc. Jobs Courageous Sailing
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