Posted: Dec 24, 2025
APPLY

Director of Advancement

Chesapeake Bay Outward Bound School - Woodlawn, MD
Salary: $120,000.00 - $140,000.00 Annually
Application Deadline: N/A

The Director of Advancement is a senior leader responsible for driving CBOBS?s fundraising and communications strategy to support an annual philanthropic revenue goal of $2.5M and positioning the organization for continued revenue growth over the next three years. This role oversees donor cultivation, grant oversight, corporate and foundation partnerships, and all advancement messaging.

The ideal candidate is strategic, highly organized, and capable of building and analyzing campaigns to attract new donors and nurture existing ones for increased and regular giving. They must be comfortable with solicitation and possess an executive presence for collaboration with the Executive Director, Board and Development Committee. Strong leadership skills required to manage a team of five direct reports. Passion for youth, education, or the outdoors is a plus! This is a hybrid position and serves in Baltimore and Washington, DC.

Fundraising Strategy & Execution

  •  Develop and lead a comprehensive advancement plan to meet the $2.5M annual revenue target.
  •  Manage a portfolio of major donors, corporate partners, and foundations.
  •  Oversee grant strategy and proposal development.
  •  Lead donor cultivation, stewardship, and prospecting efforts, with an emphasis on in-person meetings in Baltimore and DC.
  •  Lead Board and Advisory Board engagement in fundraising efforts.
  •  Lead creative development and flawless execution of the annual Cornerstone fundraising event and other donor-facing initiatives.

Leadership and management

  •  Lead a team of five direct reports, overseeing effective and timely staff recruitment, onboarding, training, and performance management.
  •  Align advancement goals with organizational strategy and annual budget.
  •  Develop and monitor individual work plans and goals for each staff member that support the Development plan.
  •  Manage department budget, forecasting, and donor acknowledgement processes.
  •  Ensure effective team use of Salesforce, Workboard, iWave, and other tools for donor research, tracking, and reporting.

 

Apply Here


PI280914050