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Associate School Director

Tres Rios, Costa Rica

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Option for partial remote work

Reports to: Executive Director, OBCR

Updated: April 2026


ORGANIZATIONAL OVERVIEW

Outward Bound Costa Rica (OBCR) operates in strategic partnership with the US-based Hurricane Island Outward Bound School (HIOBS) to expand its geographic reach and deepen program impact within Costa Rica and Central America. As a nonprofit leader in experiential education, OBCR provides transformative outdoor expeditions that inspire leadership, resilience, environmental stewardship, and cultural awareness. OBCR is entering a period of growth focused on strengthening operations, financial sustainability, and expanding program offerings across Costa Rica and the broader region.


POSITION SUMMARY

The Associate School Director (ASD) is a senior management position responsible for providing day-to-day leadership across operations, finance, and administration while driving strategic growth through new revenue-generating educational partnerships. This role serves as the primary integrator across OBCR functions and ensures alignment between program delivery, financial performance, and organizational strategy within a matrixed structure with HIOBS. The ASD works closely with the Executive Director, the OBCR Board, and the HIOBS leadership team to execute the mission of OBCR, and directly supervises an OBCR management team of three (program operations, finance/administration, and facilities).

ESSENTIAL DUTIES AND RESPONSIBILITIES

Organizational Leadership

  • Collaborate with the OBCR Executive Director to provide senior-level oversight of program operations, administration/finance, and facilities
  • Translate strategic priorities into operational execution plans
  • Ensure alignment across Program, Admissions, Marketing, and Educational Partnerships functions
  • Support annual planning, budgeting, and organizational goal-setting

Financial Management & Performance

  • Oversee budgeting, forecasting, and financial performance
  • Monitor key drivers including enrollment, revenue, and cost structure
  • Drive operational efficiency and resource allocation
  • Ensure compliance with Costa Rican and U.S. nonprofit standards

Revenue Growth & Educational Partnerships

  • Develop new Costa Rican and regional (Central America) revenue streams through institutional partnerships
  • Build and manage a pipeline of schools, universities, and NGOs
  • Lead partner acquisition, relationship management, and retention
  • Collaborate with program operations and marketing to align offerings with partner needs
  • Represent OBCR at conferences and external events

Collaboration

  • Work closely with Program Leadership on course design, scheduling, and logistics
  • Collaborate with Marketing on outreach, brand positioning, and lead generation
  • Coordinate with Admissions to ensure seamless enrollment and partner experience
  • Serve as liaison between OBCR and partner institutions pre- and post-course

Operations & Systems

  • Improve internal systems including CRM, administrative workflows, and reporting
  • Ensure accurate and timely information flow across departments
  • Drive continuous improvement in operational processes and data systems
  • Support program delivery logistics and quality assurance

Risk Management & Program Oversight

  • Participate in on-call and emergency response systems
  • Support risk management protocols and incident response
  • Ensure program quality, safety, and student experience standards are upheld

Team Leadership

  • Lead and develop staff within a matrixed organizational structure
  • Provide coaching, performance management, and professional development
  • Foster a culture of accountability, collaboration, and continuous improvement


 KNOWLEDGE AND SKILLS

  • Commitment to OBCR and HIOBS mission and values
  • Strong leadership across multiple functional areas
  • Proven experience in revenue generation and partnerships
  • Systems thinker with ability to improve processes
  • Excellent communication and relationship-building skills including proven success in managing teams and individuals
  • Ability to operate effectively in a matrixed environment
  • Fluency in English and Spanish required
  • Comfortable working in both professional and outdoor field environments

EDUCATION AND EXPERIENCE

  • Bachelor’s degree required
  • 5-7+ years of progressive leadership experience
  • Experience in education, nonprofit, or experiential learning sectors preferred
  • Experience working internationally or cross-culturally preferred

COMPENSATION PACKAGE

This position offers a competitive compensation package and benefits.


Applications are due by June 6, 2026.

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