The Executive Director (ED) at the Chesapeake Bay Outward Bound School serves as the senior staff member overseeing the execution of strategy, mission, policies, organization, funding, programs, and operation within Outward Bound National’s philosophy and guidelines. The Executive Director reports, and is accountable, to the CBOBS’s Board of Trustees. The Executive Director is expected to report to the board on strategy and budget, and to work collaboratively with board members to assure the school is responsive to local interests.


  • Establish and implement operating plans, organization structure and programs to achieve significant lasting life skills impact on participating students and organizations.
  • Provide effective leadership, motivation, and direction to the CBOBS’s staff and volunteers to enable the school to deliver rich, varied and comprehensive programs to reach a wide spectrum of students from the greater Baltimore-Washington, DC metropolitan area.
  • Develop a “full line” of programs in service to the operating region, consistent with community needs, which help make the community a better place to live.
  • Lead the CBOBS’s fundraising initiatives from individuals, foundations, corporations, government agencies, community leaders and schools with the assistance of the Board of Trustees. Meet annual fundraising objectives and cultivate longer-term sources of funding.
  • Plan for, hire, train and professionally manage top quality staff.
  • Provide effective leadership, motivation, and direction to school, staff, and volunteers.
  • Ensure that all programs are designed to effectively teach to Outward Bound’s established outcome measures and are run in accordance with Outward Bound National Safety Policies and Standards.
  • Build strong long-term relationships with the school’s customers (local school districts, charter schools and youth organizations) and its support structure (the CBOBS’s Board of Trustees, National senior management and local community leaders).
  • Establish partnerships with local youth development and outdoor activity organizations that can add capabilities and experiences to enrich the CBOBS’s programs with limited incremental cost.
  • Plan for and manage school operations and facilities efficiently and effectively to best balance cost minimization and quality program delivery.
  • Prepare challenging, yet achievable, plans and budgets and manage within approved budget.
  • Solidify and grow operations, program, partnerships, and staff in the Washington, DC office.

Minimum Qualifications / Requirements

  • Demonstrated strong leadership, people management and motivation ability.
  • Entrepreneurial zeal with a passion for the Outward Bound mission and a commitment to the value of service.
  • Energetic, self-starting and resourceful attitude
  • Effective working in a group environment requiring team building, flexible multi-tasking and careful time and expense management.
  • Ability to represent self and Outward Bound effectively with strong presence in diverse public situations.
  • Comfortable and effective relating to potential significant individual donors and requesting donations.
  • Computer literate (Microsoft and Google Suite, database proficiency).
  • Ability to learn and become proficient with emerging technology

Desirable Qualifications:

  • Knowledge of legislators and legislative process in Maryland and DC.
  • Knowledge of the communities in the Baltimore-Washington metro area and the Baltimore and DC school systems.
  • Experience in managing small group outdoor experiential life skills learning programs

Education and Work Experience: 

  • Bachelor degree required. Masters degree preferred.
  • Experience in community service organizations serving city youth. Experience with outdoor education/experiential learning or other education or youth development organizations desirable.
  • Some Outward Bound experience is preferred.
  • A minimum of five years in a managerial position with P&L responsibility.
  • Experience in, and success at, fundraising from individuals and organizations.


  • Employer contribution of 75% for Medical, Dental, & Vision insurance through CareFirst BlueChoice for the employee and their children, if applicable.
  • Paid Time Off (15 days is the base starting accrual, our handbook allows for us to offer Director-level positions a starting accrual of 20 days)
  • Up to Eight (8) weeks of paid Family/Medical leave
  • Eleven (11) paid holidays.
  • 401(k) with a match. Employees are eligible for participation after 6 months of employment. Current match is 6% of the employee’s salary.
  • Long-term disability, short-term disability, AD&D insurance, and a $25,000 life insurance policy at no cost to the employee.
  • Pre-tax Saving Cafeteria Plan: Healthcare Flexible Spending Account (FSA), Dependent Care Flexible Spending Account (FSA), Health Savings Account (HSA)
  • Pre-tax Commuter/Transit Benefits.
  • Employee Assistance Program (EAP).
  • Mutual of Omaha Supplemental Insurance.
  • Pro Deals: Discounts from outdoor industry vendors for outdoor professionals.
How to Apply

Chesapeake Bay Outward Bound School has retained Higher Talent, Inc. to manage the recruitment process. Candidates will complete comprehensive reference and background checking. Interested candidates should direct inquiries to:

Laurie Sloss, Executive Search Consultant,, 301-395-9714.

Chesapeake Bay Outward Bound School prohibits discrimination against any student or applicant because of race, color, religion, sex, gender, ethnic or national origin, sexual orientation, qualified individuals with disabilities on the basis of disability, or any other category which may be protected by applicable state or federal law. Chesapeake Bay Outward Bound School also promotes respect for all people and will not tolerate harassment based on any of these characteristics nor on differences based on gender identity or expression.