Founded in 1986, Baltimore Chesapeake Bay Outward Bound School’s (CBOBS) mission is to change lives through challenge and discovery. Outward Bound is an international educational movement, founded by Kurt Hahn, dedicated to the idea that people are capable of far more than they know.

More information about CBOBS can be found at 

Position Summary

The Chief Operating Officer (COO) oversees the organization's finances and leads Human Resources (HR), Administration, and Facilities. The incumbent is pivotal in steering the organization's financial and operational strategies. As a core member of the Leadership Team, the COO collaborates closely with the Executive Director (ED), offering strategic insights and operational expertise to drive the organization towards its goals. By effectively managing financial resources, optimizing HR processes, and ensuring smooth administrative and facility operations, the COO plays a vital role in enhancing organizational efficiency and sustainability.

The COO position is a hybrid position located in the Baltimore/Washington metropolitan area.

Essential Duties and Responsibilities 

The essential functions include, but are not limited to the following:

Finance and Accounting Leadership

  • Oversee all accounts, ledgers, and reporting systems ensuring compliance with appropriate GAAP standards and regulatory requirements.
  • Maintain internal control and safeguards for receipt of revenue, costs, and program budgets and actual expenditures.
  • Coordinate all audit activity.
  • Analyze financial data and present financial reports in an accurate and timely manner; clearly communicate monthly, quarterly, and annual financial statements; monitor progress and keep Leadership Team abreast of CBOBS financial status.
  • Assist CBOBS leadership in the annual budgeting and planning process; administer and review all financial plans and compare to actual results with a view to identify, explain, and correct variances as appropriate.
  • Support the Board of Trustees’ Finance and Investment committees around issues and trends in financial operating models and delivery.
  • Oversee all financial, project/program, and grants accounting; ensure that expenditures are consistently aligned with donor intent; collate financial reporting materials for government, corporate, and foundation grants.
  • Collaborate with program leadership to assess the financial efficacy of program operations and establish finance and administrative systems to support program operations.
  • Manage and track the performance of invested assets in keeping with policies and investment guidelines.
  • Manage organizational cash flow and forecasting by working in partnership with the Leadership Team.

Leadership, Strategy and Planning

  • Collaborate with the ED in setting and driving organizational vision, operational strategy, and hiring needs.
  • Provide leadership in strengthening internal communications with staff at all levels throughout the organization; create and promote a positive and supportive work environment.
  • Effectively communicate and present critical financial matters to the board of trustees.

Human Resources

  • Manage day-to-day HR operations, including employee relations, payroll processing, benefits administration, and workers compensation.
  • Review and refine CBOBS’ human resources policies and processes, including compensation and benefits and performance management.
  • In collaboration with Leadership Team colleagues, develop and codify consistent processes for staff recruitment, onboarding, and professional development.
  • Serve as a resource for CBOBS’ managers.


  • Oversee facilities and security management for Baltimore and Washington, DC offices.
  • Oversee IT and technology.
  • Maintain and build trusted relationships with key stakeholders, clients, partners, and vendors.
  • Oversee risk and legal/compliance.
  • Establishes policies and practices that foster transparency and accountability.
  • Serve as the primary point of contact for contracts and contract negotiations.


Minimum Qualifications

CBOBS does not expect every applicant to have every skill and qualification listed here. A strong candidate interested in growing and learning in this role will possess at least 75% of the following qualifications. If this is you, then we strongly encourage you to apply for consideration.

  • Bachelor’s degree or equivalent work experience required. MBA, CPA, or similar credential preferred.
  • 7+ years of professional experience
  • Experience leading internal administrative aspects of an organization, including finance and human resources.
  • Excellent communication and relationship building skills.
  • Ability to prioritize and manage varied bodies of work with a variety of internal and external stakeholders.
  • Strong analytical and problem-solving skills.
  • Strong knowledge of HR and compliance landscape.
  • Prior experience engaging with Board of Directors.
  • Tech savvy with CRM and cloud accounting software experience.
  • Must be able to clear federal and state background checks.


Compensation & Benefits

Salary Range: $85,000-$110,000; commensurate with experience.


  • Employer contribution of 70% for Medical, Dental, & Vision insurance through CareFirst BlueChoice for the employee and their children, if applicable.
  • Fifteen (15) days of Paid Time Off (PTO) which accrue per pay period.
  • Up to Eight (8) weeks of paid Family/Medical leave
  • Thirteen (13) paid holidays.
  • 401(k) with a match. Employees are eligible for participation after 6 months of employment. The current match is 6% of the employee’s salary.
  • Long-term disability, short-term disability, AD&D insurance, as well as 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.

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.

Outward Bound has a zero-tolerance policy for incidents of child abuse and neglect and will report any suspected abuse or neglect.