Chesapeake Bay Outward Bound School (CBOBS) is part of an international network of Outward Bound schools in over 30 countries, with 11 chartered schools in the United States. Our experiential curriculum focuses on teaching social emotional skills to predominantly middle and high school youth through challenging outdoor experiences ranging from one-day to multi-weeks in length. CBOBS serves people of all ages and from all backgrounds, but our priority is serving students from the greater Baltimore and Washington DC regions.

Founded by local community leaders in Baltimore in 1986, CBOBS’ mission is to Change Lives through Challenge and Discovery, and we do that every time a young person embarks on one of our programs. And through our Police Youth Challenge program, we pair middle school students with police officers for one-day programs that foster trust and improve communications.

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Reporting to the Chief Advancement Officer, Regional Advancement Officer (RAO) is a new, vital role on the CBOBS development team. Specific responsibilities include identifying, cultivating, soliciting, and stewarding major donors in CBOBS’ service area. This is a frontline fundraising position; and the RAO will strategically match prospective funders with CBOBS funding priorities and solicit gifts. This is not a remote position, and the RAO will be based out of CBOBS' Baltimore headquarters.


Major Gift Solicitation

  • Secure leadership gifts, special project support, and planned gifts in accordance with the organizational strategic plan and annual goals.
  • Cultivate major gift prospects, building relationships and understanding the donors’/prospects’ goals with the expressed purpose of building comprehensive donor strategies to align donor interests and organizational goals. Meet outreach and personal visit metrics as established by Chief Advancement Officer.
  • With support from the development team, move a portfolio of +100 donors and prospects through quality, strategic contacts and face-to-face visits to identify, qualify, cultivate and solicit donors to successfully close five- and six-figure gifts.
  • With support from the Development Manager, employ high-volume email, phone, social media messaging, and personalized mail outreach to secure first-time personal visits with major gifts prospects.
  • Design highly customized donor engagement plans for assigned donors.
  • Prepare and distribute reports on progress toward goals, prospect strategies and prospect contacts.
  • Work in concert with Donor Relations Manager to produce and deliver stewardship materials for donors.
  • Develop and administer budgets for major gifts program.

Management & Collaboration

  • Work closely with the CBOBS development team, program team, and Finance & Administration Director to communicate and share information and ensure accurate record keeping and fulfilment and reporting of deliverables for restricted gifts.
  • Develop productive relationships with the CBOBS program team to access their expertise in shaping donor engagement plans.
  • Perform other duties as assigned.

The First 12 Months: Leadership Priorities

The overall priorities for the first year for the RAO are to:

  • Build strong and productive relationships with the Chief Advancement Officer, the development team, and CBOBS colleagues.
  • Gain an in-depth knowledge of CBOBS and a thorough familiarity with its programs.
  • Build a highly productive portfolio of major donors and prospects in collaboration with the Chief Advancement Officer.
  • Develop and execute strategic initiatives for each prospect/funder including cultivation and solicitation strategies and ongoing stewardship.
  • Create a comprehensive plan to meet established metrics including meaningful interactions, solicitations and closing goals.
  • Contribute towards fundraising efforts to meet development team’s annual fundraising goal.
  • Work collaboratively with the CBOBS development team to build a culture of philanthropy that enhances the financial resourcing of the organization for the short-and long-term.
  • Provide recommendations on and assist in development of collateral materials for the major gifts program.


  • Bachelor’s degree from an accredited educational institution plus 5 years of front-line fundraising experience or the equivalent in education, training and experience.
  • Experience building and maintaining long-term relationships with fundraising constituents to help our donors accomplish their philanthropic goals and ambitions.
  • Expert project management skills, initiative, flexibility, discretion, and thoughtful decision-making to achieve ambitious performance objectives for outreach to constituents, personal visits (including virtual visits), gift solicitations, gift closures, and stewardship.
  • Experience researching and analyzing large groups of data to uncover prospects.
  • Excellent oral, written and research skills and be able to develop strong and productive relationships with funding sources through personal meetings, email, and telephone contact.
  • Ability to be self-motivated and disciplined to set and achieve work goals, work independently and collaboratively, handle multiple projects simultaneously in a deadline-oriented environment.
  • Ability to energetically and accurately represent CBOBS to a variety of constituents including alumni, major and leadership annual donors, board, staff, parents, and other friends of the school.
  • Proficiency in using MS Office suite and experience using CRM databases is required. Familiarity with Salesforce is preferred.
  • Uphold values consistent with the CBOBS mission.
  • Moderate regional travel required. May include evening/weekend work activity.

Compensation and Benefits

Compensation: $68,425 - $92,575; Commensurate with experience


  • Employer contribution of 75% 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
  • Eight (8) weeks of paid Family/Medical leave
  • Eleven (11) paid holidays
  • 401(k) with a match. Employees are eligible for participation after 1 year of employment.  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)
  • Aflac Supplemental Insurance
  • Pro Deals: Discounts from outdoor industry vendors for outdoor professionals


Please send a cover letter and resume addressed to Phyllis Kim, Chief Advancement Officer to Resume review will begin immediately and be ongoing.

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.