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Job DescriptionJob DescriptionSalary: $59,000-$61,000
Start Date - 8/18/2025
Who are we? Cathleen Stone Island Outward Bound School is a and State Park located in the heart of theBoston Harbor Islands, With a 200-year legacy of serving children in Boston and a 48-year partnership with the Boston Public Schools (BPS), the Island is a beacon for experiential education, empoweringyoung people through hands-on learning and skill building and outdoor adventure and exploration. We are a proud member of the network of 11 Outward Bound schools in the U.S., with a shared mission tochange lives through challenge and discovery.
Education is at the forefront of our work. Funded by a combination of philanthropy and a robustprivate events business, our outdoor educational programs are offered at no cost to families.
What is our mission and how do we achieve it?
Cathleen Stone Island Outward Bounds core mission is to build stronger, more equitable schoolcommunities by delivering free experiential learning programs that boost academic success and foster personal growth. Our research-based programs blend STEM, social-emotional, and challenge-basedlearning, giving students a unique opportunity to build life skills alongside academic ones.
Whom do we serve (students, clients, customers) We offer programs for Boston Public School middle school and high school students, -for-serviceprograms for school and youth groups, and leadership development programs for professionals. We also fund our transformational programs by hosting private and corporate events and weddings.
What is the opportunity? The Program Manager is responsible for managing school partnerships and the delivery of Connectionsprograms with a focus on safety and quality of student outcomes. Moreover the role will focus ondeveloping and updating high quality science and Social Emotional Learning resources for our programming with Boston Public School students on island and in the Boston community.
Primary responsibilities include managing aspects of planning, delivery, and day to day operations of theassigned programs including client relationships, the oversight of staff, management and communication of program schedules, program content development, and clearly reporting onprogrammatic outcomes.
This role is responsible for informal management and coaching a team of up to 30 facilitators and coursedirectors to deliver high-quality Outward Bound programming to our retail clients and school partners.The program manager team is part of a larger, dynamic, and collaborative team of managers and directors who share the responsibility of delivering mission-driven programming on Cathleen StoneIsland while maintaining the highest levels of safety and quality. This role reports to the Director ofSchool Programs. This position will manage members of our course director team and instructional staff.
What will you do?
Program Management
Oversee the direct partnership management for a portfolio of Connections school partners.
Build and cultivate strong relationships with teachers, principals, school officials, and stakeholders within the Boston Public Schools and the community.
Work collaboratively with school administration, teachers and CSIOBS staff toimplement our programming.
Develop, maintain and communicate program operations and schedules, in conjunctionwith Program Manager team, to appropriate departments (ie. Kitchen, Operations, etc.)
Ensure programs are delivered safely and in a high-quality manner quality as evidenced bysurveys, observations and data.
Collaborate with Director of School Programs on developing new and updating existing Connections SEL & science curriculum.
Identify helpful resources to assist in creating place based, experiential, outdoor education curriculum.
Support Course Director with programmatic needs for the duration of the course
Support the distribution, collection, and processing of student enrollment paperwork.
Collaborate with the Admin team to analyze survey results and implement subsequentchanges based on results.Ensure that all course and incident data is entered into the appropriate databases.
Collaborate with Family Engagement manager on student outreach and recruitment.
Ensure that school-based programs are operating in accordance with Boston Public School policies
Personnel Management
Lead, manage, and coach a team of course directors and instructors to support studentsthrough social emotional learning.
Develop instructors as strong facilitators and leaders through their OutwardBound experience.
Model leadership that reflects Outward Bounds culture and values and create spaces thatempower instructors and course directors.
Conduct regular observation and coaching sessions with instructors to assess, strengthen,and grow their skill set.
Complete performance reviews and individual development plans (IDP).
Oversee timecards for course directors and instructors, ensuring overtime policies and expectation of hours worked is accurate and aligned with staffing schedule.
Other duties as assigned.
QUALIFICATIONS
A bachelors degree and 5 years of commensurate experience.
Knowledge and field experience with urban school-based programs and/orOutward Bound.
At least two years of experience supervising employees.
At least three years of program management experience.
Passion for social justice, environmental stewardship, climate change responsiveness,natural resource and facilities management, and the outdoors.
An understanding and commitment to the implementation Culturally andLinguistically Sustaining Practices.
Fluency (writing and speaking) in Spanish is a plus.
Familiarity with computer-based systems like Microsoft Outlook, Word, Excel, Teams andGoogle Drive.
Experience with Customer Relations Management databases i.e. Salesforce or booking system (Triple Seat) a plus.
WORK CONDITIONS
While the position will work primarily on the island, expect to spend some time workingremotely or at our partner schools.
Environmental fluctuations are typical of the New England coast, and can include hot,humid weather, and unseasonably cool, rainy, and windy coastal weather; must becomfortable working outside in either of these extremes for extended periods of time.
All positions reporting hours to the island are asked to assist loading/unloading cargo fromthe boat as able. This involves lifting and walking with parcels upwards of 50 lbs on and offmoving docks and up/down ramps
Must be able to be on feet an average of 5+ hours per day.
Must be comfortable on board a variety of boats and working around the water.
Must have the mental and physical stamina to maintain a high quality of job performance while working in a dynamic fast-paced environment, often performing hours exceeding typical workday
COMPENSATION AND BENEFITS
Competitive salary, commensurate with experience. Employer sponsored health insurance with the option to select between three comprehensive plans. Premier dental and vision plan. 401(k) retirement plan with competitive match. Generous paid time off including, vacation, holidays, personal days, parental and sick leave. Flexible scheduling, pursuant to position. Work that engages a diverse and dynamic community of educators and other professionals, with the shared vision of shaping a better future for Bostons youth. A quality work life in Bostons vibrant Seaport district with frequent access to the natural wonders and positive impacts of Cathleen Stone Island.
Cathleen Stone Island Outward Bound School is an equal opportunity employer and actively seeks staff as diverse as the communities it serves. All qualified applicants will receive consideration for employment without regard to , , , , , , , status, protected veteran status, or any other characteristic protected by law.
Outward Bound has a zero-tolerance policy for incidents of child abuse and neglect. Protecting our minor students against abuse and neglect is of the highest priority.
Start Date - 8/18/2025
Who are we? Cathleen Stone Island Outward Bound School is a and State Park located in the heart of theBoston Harbor Islands, With a 200-year legacy of serving children in Boston and a 48-year partnership with the Boston Public Schools (BPS), the Island is a beacon for experiential education, empoweringyoung people through hands-on learning and skill building and outdoor adventure and exploration. We are a proud member of the network of 11 Outward Bound schools in the U.S., with a shared mission tochange lives through challenge and discovery.
Education is at the forefront of our work. Funded by a combination of philanthropy and a robustprivate events business, our outdoor educational programs are offered at no cost to families.
What is our mission and how do we achieve it?
Cathleen Stone Island Outward Bounds core mission is to build stronger, more equitable schoolcommunities by delivering free experiential learning programs that boost academic success and foster personal growth. Our research-based programs blend STEM, social-emotional, and challenge-basedlearning, giving students a unique opportunity to build life skills alongside academic ones.
Whom do we serve (students, clients, customers) We offer programs for Boston Public School middle school and high school students, -for-serviceprograms for school and youth groups, and leadership development programs for professionals. We also fund our transformational programs by hosting private and corporate events and weddings.
What is the opportunity? The Program Manager is responsible for managing school partnerships and the delivery of Connectionsprograms with a focus on safety and quality of student outcomes. Moreover the role will focus ondeveloping and updating high quality science and Social Emotional Learning resources for our programming with Boston Public School students on island and in the Boston community.
Primary responsibilities include managing aspects of planning, delivery, and day to day operations of theassigned programs including client relationships, the oversight of staff, management and communication of program schedules, program content development, and clearly reporting onprogrammatic outcomes.
This role is responsible for informal management and coaching a team of up to 30 facilitators and coursedirectors to deliver high-quality Outward Bound programming to our retail clients and school partners.The program manager team is part of a larger, dynamic, and collaborative team of managers and directors who share the responsibility of delivering mission-driven programming on Cathleen StoneIsland while maintaining the highest levels of safety and quality. This role reports to the Director ofSchool Programs. This position will manage members of our course director team and instructional staff.
What will you do?
Program Management
Oversee the direct partnership management for a portfolio of Connections school partners.
Build and cultivate strong relationships with teachers, principals, school officials, and stakeholders within the Boston Public Schools and the community.
Work collaboratively with school administration, teachers and CSIOBS staff toimplement our programming.
Develop, maintain and communicate program operations and schedules, in conjunctionwith Program Manager team, to appropriate departments (ie. Kitchen, Operations, etc.)
Ensure programs are delivered safely and in a high-quality manner quality as evidenced bysurveys, observations and data.
Collaborate with Director of School Programs on developing new and updating existing Connections SEL & science curriculum.
Identify helpful resources to assist in creating place based, experiential, outdoor education curriculum.
Support Course Director with programmatic needs for the duration of the course
Support the distribution, collection, and processing of student enrollment paperwork.
Collaborate with the Admin team to analyze survey results and implement subsequentchanges based on results.Ensure that all course and incident data is entered into the appropriate databases.
Collaborate with Family Engagement manager on student outreach and recruitment.
Ensure that school-based programs are operating in accordance with Boston Public School policies
Personnel Management
Lead, manage, and coach a team of course directors and instructors to support studentsthrough social emotional learning.
Develop instructors as strong facilitators and leaders through their OutwardBound experience.
Model leadership that reflects Outward Bounds culture and values and create spaces thatempower instructors and course directors.
Conduct regular observation and coaching sessions with instructors to assess, strengthen,and grow their skill set.
Complete performance reviews and individual development plans (IDP).
Oversee timecards for course directors and instructors, ensuring overtime policies and expectation of hours worked is accurate and aligned with staffing schedule.
Other duties as assigned.
QUALIFICATIONS
A bachelors degree and 5 years of commensurate experience.
Knowledge and field experience with urban school-based programs and/orOutward Bound.
At least two years of experience supervising employees.
At least three years of program management experience.
Passion for social justice, environmental stewardship, climate change responsiveness,natural resource and facilities management, and the outdoors.
An understanding and commitment to the implementation Culturally andLinguistically Sustaining Practices.
Fluency (writing and speaking) in Spanish is a plus.
Familiarity with computer-based systems like Microsoft Outlook, Word, Excel, Teams andGoogle Drive.
Experience with Customer Relations Management databases i.e. Salesforce or booking system (Triple Seat) a plus.
WORK CONDITIONS
While the position will work primarily on the island, expect to spend some time workingremotely or at our partner schools.
Environmental fluctuations are typical of the New England coast, and can include hot,humid weather, and unseasonably cool, rainy, and windy coastal weather; must becomfortable working outside in either of these extremes for extended periods of time.
All positions reporting hours to the island are asked to assist loading/unloading cargo fromthe boat as able. This involves lifting and walking with parcels upwards of 50 lbs on and offmoving docks and up/down ramps
Must be able to be on feet an average of 5+ hours per day.
Must be comfortable on board a variety of boats and working around the water.
Must have the mental and physical stamina to maintain a high quality of job performance while working in a dynamic fast-paced environment, often performing hours exceeding typical workday
COMPENSATION AND BENEFITS
Competitive salary, commensurate with experience. Employer sponsored health insurance with the option to select between three comprehensive plans. Premier dental and vision plan. 401(k) retirement plan with competitive match. Generous paid time off including, vacation, holidays, personal days, parental and sick leave. Flexible scheduling, pursuant to position. Work that engages a diverse and dynamic community of educators and other professionals, with the shared vision of shaping a better future for Bostons youth. A quality work life in Bostons vibrant Seaport district with frequent access to the natural wonders and positive impacts of Cathleen Stone Island.
Cathleen Stone Island Outward Bound School is an equal opportunity employer and actively seeks staff as diverse as the communities it serves. All qualified applicants will receive consideration for employment without regard to , , , , , , , status, protected veteran status, or any other characteristic protected by law.
Outward Bound has a zero-tolerance policy for incidents of child abuse and neglect. Protecting our minor students against abuse and neglect is of the highest priority.