Head of School – Private School Leadership
Providence School
- St. George
- Not disclosed
- Permanent full-time
- Updated 10/04/2026
Head of School (CEO) accountable for strategy, performance, and sustainability. Responsible for enrollment growth, financial targets, and academic outcomes. Leads leadership team, drives alignment across divisions, and reports to the Board on performance, risk, and progress.
The Opportunity
The Head of School serves as the Chief Executive of Providence School and is accountable for the overall strategic direction, performance, and long-term sustainability of the institution. The role is responsible for delivering enrollment and financial targets, achieving strong academic outcomes, and strengthening the School’s position within Barbados and the wider Caribbean.
The Head of School operates at a strategic level, setting direction, establishing frameworks, and leading a high-performing leadership team, while ensuring effective day-to-day execution through Principals and senior staff.
The Head of School will also serve as the primary liaison to the Board of Management, providing regular reporting on performance, risk, and strategic progress.
Key Responsibilities
Financial Viability
- Ensure long-term financial sustainability through a clear revenue strategy, cost discipline, and resource allocation
- Develop and deliver diversified revenue streams, including grants, facility use, strategic partnerships, and fundraising
- Oversee financial planning, forecasting, and risk management, ensuring alignment between enrollment, staffing, and financial performance
Enrollment Management
- Lead enrollment strategy, including admissions, retention, and pipeline management
- Strengthen the Secondary School offering and conversion from Elementary
- Position the School to attract and retain a diverse and mission-aligned student body
Marketing, Visibility & Development
- Elevate the School’s brand and market positioning locally, regionally, and internationally
- Lead development and fundraising strategy, including donor cultivation and strategic partnerships
- Serve as a visible ambassador, strengthening relationships with families, alumni, and the wider community
Educational Offering & Student Outcomes
- Set school-wide educational priorities and standards aligned with the School’s mission
- Hold Principals accountable for curriculum delivery, teaching quality, and student outcomes
- Drive continuous improvement in academic performance and student experience
People & Culture
- Build and lead a high-performing leadership team with clear accountability
- Establish structured performance, development, and feedback frameworks
- Lead complex people matters and support a strong, values-driven culture
- Strengthen alumni and community engagement to support long-term sustainability
Governance & Operations
- Partner effectively with the Board of Management on strategy, reporting, and risk
- Strengthen organizational clarity, decision-making, and accountability structures
Facilities & Learning Environment
- Oversee campus planning and ensure a safe, high-quality learning environment aligned with enrollment growth and program needs
Candidate Profile
- Strategic, results-oriented leader with strong financial and commercial acumen
- Proven ability to lead growth, drive accountability, and deliver measurable outcomes
- Strong communicator and relationship builder, capable of engaging parents, staff, Board, and community
- Demonstrated ability to navigate complex situations with sound judgment, maintaining composure and effective decision-making under pressure
- Alignment with Providence’s values of Goodness, Discipline, and Knowledge is essential.
Qualifications & Experience
- Master’s degree in Education, Educational Leadership, Business Administration, or related field
- 10+ years of progressive leadership experience, including senior leadership roles in education or a comparable environment
- Proven success in driving enrolment growth, improving academic outcomes, and building high-performing teams
- Experience overseeing financial planning, budgeting, and resource allocation
- Strong understanding of governance and policy frameworks
- Experience with crisis management and leading organizations through periods of change or uncertainty is highly desirable
- Experience with fundraising, partnerships, or institutional advancement is an asset
Compensation
A competitive compensation package will be offered, comprising a base salary and a variable performance-based component linked to the achievement of enrollment, financial, and academic outcomes, commensurate with experience and qualifications.
Candidates must have the legal right to live and work in Barbados
Only shortlisted candidates will be contacted.
