Director of Advancement

Company: Chesapeake Bay Outward Bound School Inc
Location: Gwynn Oak
Posted on: January 21, 2026

Job Description:

Job Description Job Description Description: 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 Director collaborates closely with the Executive Director, Board, and Development Committee to grow a diversified pipeline of supporters and elevate CBOBS’s visibility across Baltimore and Washington, DC. 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. Requirements: The essential functions include but are not limited to the following: 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; Lead philanthropic communications strategy and ensure consistent, compelling messaging across all advancement communications; and Partner with program staff to highlight impact stories for donor audiences. 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; Use CRM to monitor fundraising progress and report weekly and quarterly to the ED and Board; Manage department budget, forecasting, and donor acknowledgement processes; and Ensure effective team use of Salesforce, Workboard, iWave, and other tools for donor research, tracking, and reporting. Minimum Qualifications (Knowledge, Skills, and Abilities) At least 5–8 years’ leadership experience in advancement or development with a successful track record in: Securing six-figure gifts and managing a multi-million dollar donor pipeline; Meticulous grant oversight and proposal review skills; Experience leading cross-functional teams; Proficiency with donor databases (Salesforce preferred), reporting, and data analysis; Excellent communication, storytelling, and interpersonal skills; and Working knowledge of philanthropic communities in Baltimore and Washington, DC, and a willingness to travel regularly to both areas. Benefits Employer contribution of 70% for Medical, Dental, & Vision insurance 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) retirement plan with a match. Employees are eligible for participation after 6 months of employment. The current match is 3% of the employee’s salary. Long-term disability, short-term disability, 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. Physical Demands and Work Environment The physical demands described here are representative of those that must be met by an employee to successfully perform the essential functions of this position. Reasonable accommodations may be made to enable individuals with disabilities to perform the functions. Ability to sit at a desk or computer 90% of the time or greater; and Comfortable in outdoor settings with ability to contribute to CBOBS team tasks from time to time, such as organizing camping equipment. Note This job description in no way states or implies that these are the only duties to be performed by the employee(s) of this position. Employees will be required to follow any other job-related instructions and to perform any other job-related duties requested by any person authorized to give instructions or assignments. All duties and responsibilities are essential functions and requirements and are subject to possible modification to reasonably accommodate individuals with disabilities. To perform this job successfully, the employee(s) will possess the skills, aptitudes, and abilities to perform each duty proficiently. Some requirements may exclude individuals who pose a direct threat or significant risk to the health or safety of themselves or others. The requirements listed in this document are the minimum levels of knowledge, skills, or abilities. This document does not create an employment contract, implied or otherwise, other than an at-will relationship. 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.

Keywords: Chesapeake Bay Outward Bound School Inc, Wilmington , Director of Advancement, PR / Public Relations , Gwynn Oak, Delaware