Organization Summary

Founded in 1986, 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. The Chesapeake Bay Outward Bound School (CBOBS) is a non-profit, outdoor educational organization with programs that deliver character development and self-discovery in the wilderness, in the city, and in school. CBOBS operates programs in Baltimore City, the District of Columbia, the Appalachian Trail in MD and PA, the Potomac River, the Dolly Sods Wilderness Area in WV, and the Eastern Shore of the Chesapeake Bay.

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Position Summary

Reporting to the Executive Director (ED), the Development Director is a key member of the senior leadership team. Together with the ED, they develop and execute campaign and fundraising strategies for initiatives in Baltimore and Washington, DC. Collaborating closely with the leadership team, development staff, and board members, they strengthen CBOBS's financial resources by cultivating donor relationships, expanding the donor base, and diversifying prospects. The ideal candidate will have extensive fundraising leadership experience and a goal to generate $2M annually in the region.

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 three direct reports. Passion for youth, education, or the outdoors is a plus! This is a hybrid position and serves in Baltimore and Washington, DC. A bonus structure will be available, based on mutually agreed-upon metrics created in partnership with the Executive Director and the Board of Trustees.


Essential Duties and Responsibilities

Include, but are not limited to the following:

Strategy and goal-setting

  • Develop and execute a cohesive campaign strategy and annual fundraising plan for CBOBS in partnership with the ED, members of the Development team, and Board Development Committee, which will generate $2M per year from annual and monthly giving, major donors (individuals, companies and foundations), government grants, and planned gifts.
  • Contribute to the development and implementation of CBOBS’s overall financial and strategic plans by partnering with the ED and the Leadership Team.

Leadership and management

  • Lead a high-performing team of three direct reports, overseeing effective and timely staff recruitment, onboarding, training, and performance management.
  • Develop and monitor individual work plans and goals for each staff member that support the Development plan.
  • Communicate and collaborate effectively and regularly with the Sales and Marketing teams to maximize revenue and promotional opportunities for CBOBS across departments.


  • Develop and implement a high-performing fundraising strategy with a strong emphasis on prospect pipeline development for annual and major gifts. Focus on the cultivation and stewardship of prospects and donors to secure significant long-term contributions.
  • Personally manage a portfolio of high-net-worth individuals, and corporate and foundation donors, researching, cultivating, developing proposals, asking for, and stewarding support to meet annual fundraising goals.
  • Oversee the development, editing, and execution of Development team proposals, ensuring consistency and quality, and seeking ED approval where needed. Collaborate with the Development team, ED, Leadership Team and and other program staff regarding content development.
  • Organize and attend the Board Development Committee meetings including agenda preparation, identifying and advising on prospects for discussion, briefing the Committee co-chairs, etc. Engage Board members, and other volunteer leaders, in between meetings to ensure follow-up on actions identified.
  • Ensure the effective organization of CBOBS's annual 'Cornerstone' fundraising event, engaging the event consultant promptly and securing Development team support for board and donor engagement as sponsors and for ticket sales.

Monitoring and reporting progress

  • Oversee the Development team’s use of CBOBS's online management tools (Salesforce, SharePoint/OneDrive, MS Teams, WorkBoard, etc.) and ensure efficient and accurate record-keeping and communication.
  • Monitor and report monthly on the progress of fundraising revenue for the year, and provide further updates as needed for the ED and Development Committee.
  • Ensure donors are acknowledged and pledge reminders are prepared promptly.
  • Prepare cash flow forecasts and budget re-forecast for fundraising revenue and report as needed by the ED and Chief Operating Officer.
  • Present to the Development Committee and Board as required regarding Development performance.
  • Manage the Development department’s annual budget.

Minimum Qualifications (Knowledge, Skills, and Abilities)

At least 5-8 years’ fundraising leadership experience and a successful track record in:

  • Major gift programs and capital campaigns, including prospect research, cultivation, personal solicitation, acknowledgment, and stewardship.
  • Securing six figure major gifts.
  • Budgeting, work plan development, report preparation and analysis, and performance evaluation.
  • Managing staff effectively through annual goal setting, feedback, mentoring, and coaching.
  • Using a donor database (ideally Salesforce) to ensure strategic and effective administration of donations and pledges, donor engagement plans, and donor and prospect activity reporting.
  • Performing effectively under pressure and meeting deadlines in a fast-paced work environment.
  • Demonstrating initiative, creativity, and commitment to achieving and exceeding results.
  • Time and project management skills with the ability to prioritize and focus on goals.
  • Excellent written and verbal presentation skills.
  • Strong interpersonal skills.
  • Willingness to travel regularly within the Baltimore and Washington, DC areas.

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.
  • Comfortable in outdoor settings with ability to contribute to CBOBS team tasks from time to time, such as organizing camping equipment.


Salary Range: $115,00-$130,000; 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.


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.