HEAD OF ASSESSMENT - Senior Leadership
August 2026

ABOUT THE SCHOOL

Cayman Prep and High School is a private, co-educational Christian school with over 1,000 students ranging from Kindergarten to Year 13 and offers a British-based international curriculum leading to (I)GCSE and A-level qualifications. The school is renowned for providing a stimulating learning environment in which students become critical, creative thinkers, responsible citizens, and lifelong learners. This is reflected in a consistent record of outstanding academic achievements, strong pastoral care, and a wide range of extra-curricular activities.

Cayman Prep and High School is seeking an exceptional educational leader to join its high-performing High School team from August 2026 as Head of Assessment. This represents an outstanding opportunity for an accomplished and analytical educational professional who is passionate about assessment for learning, academic excellence, and driving whole-school improvement through high-quality assessment systems and data-informed practice.

The school is looking for a reflective, inspirational, and forward-thinking leader who is motivated by working with engaged learners, values professional collaboration, and is excited by the opportunity to further develop assessment practices within a supportive environment that invests in its people and empowers educators to make a meaningful impact.

ROLE OVERVIEW

The Head of Assessment reports directly to, and works under the guidance of, the High School Principal. As a member of the High School Leadership Team, he / she will contribute to the professional leadership and management of the School, in alignment with the Christian principles and ethos of the United Church in Jamaica and the Cayman Islands.

The successful candidate will lead, deliver and quality assess the school's Assessment Policy and whole school systems of assessment at Key Stage 3, 4 and 5. He / She will also carry out the professional duties of a teacher as required (up to 50% teaching load).

CANDIDATE REQUIREMENTS

• The successful candidate must hold a recognised degree along with an internationally recognised teaching qualification such as a PGCE, Bachelor of Education, or equivalent, and will have significant recent experience in assessment leadership, curriculum delivery, and teaching within a British curriculum environment.
• Must be an exceptional educational leader with demonstrated experience in assessment leadership, organisation, strategic planning, and whole-school improvement.
• Must have strong and up-to-date knowledge of assessment systems and practices within the British National Curriculum, including experience with Key Stage 3, IGCSE, and A-level assessment frameworks.
• Must be highly skilled in the analysis and interpretation of assessment data to support student progress, raise attainment, and inform teaching and learning strategies.
• Must have experience developing and implementing whole-school assessment policies, procedures, and reporting systems.
• Must be an excellent classroom practitioner with a proven ability to inspire students and staff while maintaining high academic standards.
• Must have the ability to lead professional development and support colleagues in the effective use of assessment for learning strategies.
• Must possess excellent communication skills, both oral and written, and be able to work collaboratively with staff, students, and parents.
• Must be able to manage multiple priorities effectively, work under pressure, and maintain a high level of attention to detail.
• Must have experience with SIMS and be fully IT literate, with strong data management and reporting skills.
• Must be willing to be involved in a wide range of school-related activities and contribute positively to the wider life of the school community.
• Will be expected to uphold and fully adhere to and support the Christian ethos of the school.
• Prior experience teaching in a multicultural international school environment is an advantage.

REMUNERATION AND BENEFITS

• Salary range for the position listed above is £72,000 - £84,000 per annum commensurate with experience based on the school's point salary scale. Tax FREE
• Generous medical insurance plan – medical premium cost paid for employee at 100%
• Contribution to a pension plan
• Exceptional monetary relocation allowance on arrival
• Return Airfare on initial relocation
• Annual travel allowance
• Discounted school fees: first child 100% and 50% for up to 2 additional dependent children
• Generous school holidays
• Continued Professional Development Opportunities throughout the School Year

SAFEGUARDING

Cayman Prep and High School is fully committed to safeguarding the welfare of our children and young people and expects the same commitment from all our employees. All successful candidates will be subject to enhanced pre-employment clearance including prohibition from teaching checks, identity checks, criminal background checks, qualification checks and employment checks to include an exploration of any gaps in employment and three satisfactory employment checks.