Program Manager (Discovery, Expeditions, and Training)

CATHLEEN STONE ISLAND OUTWARD BOUND
Boston, MA

Job Description

Job Description

Description:

The Program Manager (Discovery, Expeditions, and Training) is responsible for managing program logistics and the delivery of Discovery and Expedition programs with a focus on safety and quality of student outcomes.

Primary responsibilities include managing aspects of planning, delivery, and day to day operations of the assigned programs including client relationships, the training and oversight of staff, management and communication of program schedules, program content development, and clearly reporting on programmatic outcomes.

This role is responsible for informal management and coaching a team of up to 30 facilitators and course directors 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 Stone Island while maintaining the highest levels of safety and quality. This role reports to the Associate Director of Group Programs and Training. This position will manage members of our course director team and instructional staff.

This role is responsible for informal management and coaching a team of up to 30 facilitators and course directors 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 Stone Island while maintaining the highest levels of safety and quality. This role reports to the Associate Director of Group Programs and Training. This position will manage members of our course director team and instructional staff.

Program Management

  • Oversee the direct partnership management for a portfolio of school partners and expedition partners.
  • Develop, maintain and communicate program operations and schedules, in conjunction with Program Manager team, to appropriate departments (ie. Kitchen, Operations, etc.)
  • Ensure programs are delivered safely and in a high-quality manner quality as evidenced by surveys, observations and data.
  • Support Course Director with programmatic needs for the duration of the course
  • Build and maintain positive working relationships with community and school partners.
  • Support the distribution, collection, and processing of student enrollment paperwork.
  • Collaborate with the Admin team to analyze survey results and implement subsequent changes based on results.
  • Assist Program Director in developing and reconciling an annual budget.
  • Ensure that all course and incident data is entered into the appropriate databases.
  • Collaborate with Family Engagement manager on student outreach and recruitment.

Personnel Management

  • Lead, manage, and coach a team of course directors and instructors to support students through social emotional learning.
  • Collaborate with the Associate Director of Training and Group Programs to plan, develop, and facilitate regular training and professional development opportunities.
  • Develop instructors as strong facilitators and leaders through their Outward Bound experience.
  • Model leadership that reflects Outward Bound’s culture and values and create spaces that empower 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.

General Workplace Responsibilities

  • Attend and participate in CSIOBS Staff Meetings and other site activities/events.
  • Course direct, facilitate, site manage (if certified), and/or belay monitor (if certified) as needed or requested by a supervisor.
  • Other duties as assigned.
Requirements:

Qualifications

  • A bachelor’s degree and 5 years of commensurate experience.
  • Knowledge and field experience with urban school-based programs and/or Outward 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.
  • Fluency (writing and speaking) in Spanish is a plus.
  • Familiarity with computer-based systems like Microsoft Outlook, Word, Excel, Teams and Google 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 working remotely 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 be comfortable working outside in either of these extremes for extended periods of time.

Physical Requirements:

  • All positions reporting hours to the island are asked to assist loading/unloading cargo from the boat as able. This involves lifting and walking with parcels upwards of 50 lbs on and off moving 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.
Posted 2026-07-16

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