Job Description

Positions reports to: Head of School

Job Types: Full-time, Contract

Pay: $60,000-$120,000 per year (commensurate with experience)

Job Type: Full-time

CLICK HERE to review full job description.

Chesapeake Bay Academy (CBA) seeks a mission-driven, strategic, and relationship-centered Chief Advancement Officer (CAO) to help shape the next chapter of a highly respected independent school serving students with learning differences.

Reporting directly to the Head of School and serving as a member of the senior leadership team, the CAO will lead advancement efforts across philanthropy, donor engagement, stewardship, endowment development, strategic partnerships, tax-credit giving, grants, sponsorships, alumni relations, and community engagement.

This role offers a rare opportunity to help build the future of advancement at a school with a strong mission, an engaged community, and significant potential for growth. The successful candidate will maintain and strengthen current advancement efforts while helping create a sustainable, diversified, and mission-aligned model for future success.

The CAO will partner closely with the Head of School, Board of Trustees, donors, families, alumni, faculty, staff, and community partners to ensure that philanthropic investment directly supports student success, innovation, accessibility, and long-term institutional sustainability.

The ideal candidate is energized by building systems, cultivating relationships, leading change, and translating mission into meaningful philanthropic support.

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.

Candidate Profile & Qualifications

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.

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 review the full job profile and 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 ***email_hidden***

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