Chief Advancement Officer

The Chief Advancement Officer serves as Chesapeake Bay Academy’s senior advancement leader and strategic partner to the Head of School and Board of Trustees.

The CAO is responsible for strengthening philanthropic support, building donor confidence, increasing advancement effectiveness, and ensuring alignment between advancement strategy and institutional priorities.

Advancement Strategy

• Develop and lead a comprehensive advancement strategy aligned with CBA’s mission, strategic plan, and financial priorities.
• Establish fundraising goals, advancement priorities, and long-term growth plans in partnership with the Head of School and Board leadership.
• Evaluate advancement effectiveness and recommend improvements to systems, structures, staffing, technology, and resource allocation.

Philanthropy and Donor Engagement

• Lead annual giving, major gifts, planned giving, endowment development, grants, sponsorships, and stewardship efforts.
• Manage a portfolio of leadership and major gift prospects.
• Partner with the Head of School and trustees on donor cultivation, solicitation, and stewardship.
• Ensure successful transition, retention, and engagement of existing donors and supporters.

Organizational Leadership

• Build reliable advancement operations, reporting systems, stewardship practices, and donor engagement processes.
• Develop a healthy culture characterized by accountability, collaboration, professional growth, and mission alignment.
• Evaluate fundraising activities and events for mission impact, donor experience, effectiveness, and return on investment.

Strategic Partnerships

• Identify opportunities for partnerships, grants, sponsorships, and mission-aligned funding opportunities.
• Collaborate with academic leaders, enrollment leaders, CERTI, CadetNet, marketing, and student support teams to strengthen philanthropic engagement and institutional impact.

VFLDS and Tax-Credit Giving

• Coordinate closely with the Virginia Foundation for Learning Disabled Students (VFLDS) and support donor engagement through Virginia’s Education Improvement Scholarships Tax Credits Program (EISTCP).
• Ensure donor clarity, stewardship excellence, compliance, and alignment between tax-credit giving and broader philanthropic goals.

Builder. Strategist. Relationship-centered leader.

The strongest candidates will combine strategic leadership, fundraising expertise, organizational development experience, and a deep commitment to mission-driven work.

• A belief in the potential of students with learning differences and the transformative power of individualized education.
• Success securing major gifts and building sustainable philanthropic support.
• Experience leading teams, managing change, and strengthening organizational effectiveness.
• Strong relationship-building skills with donors, trustees, families, volunteers, and community leaders.
• The ability to translate institutional priorities into compelling philanthropic opportunities and donor-centered cases for support.
• Strategic thinking combined with operational discipline and execution.
• High integrity, sound judgment, and commitment to ethical fundraising practices.
• Strong written and verbal communication skills.
• Curiosity, resilience, creativity, and comfort leading through change.

Experience in independent schools is valued but not required. Candidates from higher education, healthcare, nonprofit leadership, research institutions, and other mission-driven organizations are encouraged to apply.

Qualifications

• Bachelor’s degree required.
• Advanced degree, CFRE credential, or comparable professional experience preferred.
• Ten or more years of progressively responsible experience in advancement, fundraising, external relations, nonprofit leadership, or related fields.
• Demonstrated success cultivating, soliciting, and stewarding major gifts.
• Experience managing people, budgets, operations, and cross-functional initiatives.
• Ability to work effectively with executive leadership and governing boards.

Chesapeake Bay Academy believes advancement success is measured by more than annual fundraising totals. Success in this role will include:

• A clear, board-aligned advancement strategy with measurable goals and accountability structures.
• Strong retention and engagement of existing donors, sponsors, foundations, alumni leaders, and volunteers.
• Growth in major gift activity, donor retention, donor upgrades, endowment commitments, and planned giving engagement.
• Advancement revenue that demonstrates both short-term reliability and long-term diversification.
• Development of new philanthropic pathways, grants, sponsorships, partnerships, and mission-aligned funding opportunities.
• Improved return on investment across fundraising initiatives, events, staffing structures, and advancement expenditures.
• Reliable advancement operations, accurate reporting, strong stewardship practices, and disciplined donor management systems.
• Increased donor understanding of CBA’s mission, impact, and strategic priorities.
• A healthy advancement culture characterized by clarity, accountability, collaboration, and professional growth.
• Visible progress toward institutional priorities related to enrollment, innovation, student experience, faculty excellence, accessibility, and long-term financial sustainability.

The successful candidate is not expected to solve every challenge immediately. The first eighteen months should establish the relationships, systems, priorities, and strategic direction necessary for long-term success.

The Chief Advancement Officer must model the type of leadership Chesapeake Bay Academy seeks throughout the institution: student-centered, ethical, collaborative, accountable, mission-driven, and humane.

Because advancement at CBA is deeply connected to student outcomes and mission impact, the CAO is expected to be an active and visible member of the school community who develops an authentic understanding of students, families, faculty, and programs.

The strongest advancement strategies emerge from lived understanding rather than generic fundraising language.

Salary Range: $60K – $120K (commensurate with experience)

Benefits available include health, dental, vision and life insurance, 403 (b) retirement plan and match, employee assistance program (EAP), flex spending account (FSA), paid time off, and professional development/tuition assistance.

This position is primarily onsite in Virginia Beach, Virginia.

The role requires occasional evening and weekend commitments for donor engagement, board activities, community partnerships, conferences, and school events. Limited travel may be required.

Interested candidates should submit:

• Cover letter
• Resume or curriculum vitae
• Professional references

References will not be contacted without candidate knowledge and consent.

Application materials should be submitted electronically to: Debbie Ramos, Executive Assistant to the Head of School, at dramos@cba-va.org

Chesapeake Bay Academy is committed to conducting a thoughtful, equitable, and mission-aligned search process and welcomes candidates from diverse professional backgrounds who are excited by the opportunity to help shape the school’s next chapter.

Chesapeake Bay Academy is committed to fostering a community characterized by dignity, respect, belonging, and opportunity for all.

As an equal opportunity employer, Chesapeake Bay Academy does not discriminate on the basis of any status protected by applicable federal, state, or local law.