CAYMAN PREP & HIGH SCHOOL

Owned and operated by the United Church in Jamaica and the Cayman Islands

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 our students become critical, creative thinkers, responsible citizens, and lifelong learners. This is evident in our consistent record of outstanding academic achievements, pastoral care, and wide range of extra-curricular activities.

We are seeking exceptional leaders to join our high-performing High School team from August 2026. This is an outstanding opportunity for accomplished and creative educators who are passionate about child-centred education and eager to positively contribute to, and grow within, a highly respected, values-driven school community known for academic excellence and innovation.

We are looking for reflective, inspirational, and forward-thinking leaders who are inspired by working with motivated learners, value professional collaboration, and are excited by the opportunity to further develop their practice within a supportive environment that invests deeply in its people and empowers educators to make a meaningful impact.

Head of Assessment                                                                                                                              (Job Ref# B204- 26-27)

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 our 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).

The Head of Assessment is also required to:

• Strategically lead the Data Cycle process across the school to track, monitor and raise individual and group student progress.
• Monitor student progress, ensuring that all data systems are effective and efficient.
• Ensure effective and consistent formative and summative assessment methods and procedures are being planned for and delivered effectively.
• Provide Leadership, training, guidance and coaching to support staff to deepen practical data-driven teaching practices.
• Strategically lead, organize and implement student reporting practices, including written reports and parent, student and teacher consultations.
• Ensure prudent use and maximum impact of SIMS, in liaison with the Data Manager.
• Ensure the educational and operational success of the High School.
• Provide vision and strategic direction across the school.
• Formulate the aims, objectives of the schools and cement the policies through which they are to be achieved.
• Map and oversee all necessary preparation for accreditation and inspection.
• Line manage assigned Faculty staff taking them successfully through PMAP process.
• Lead on our admissions process with the Admissions Officer, ensuring correct policy is adhered to
• Provide mentoring, coaching and guidance to support teaching staff to deliver consistently good or outstanding learning and assessment for excellence in delivery.
• Be an integral part of the HLT and Inclusion Team in raising standards of learning, and assessment.
• Research best practice and develop skills to support and sustain excellence in learning and assessment.
• Actively promote a sharing of good practice from within and outside of the school.

Qualifications, experience and skills required for the Head of Assessment and Inclusion position are:

• A degree in a relevant subject and an internationally recognised teaching qualification, such as a PGCE, Bachelor of Education or H.Dip.Ed; A school-based leadership qualification would be an advantage.
• A minimum of six years of outstanding and varied teaching experience in school(s) using the British Curriculum.
• A minimum of three years Senior Educational Leadership experience.
• An in-depth and up-to-date knowledge and understanding of the National Curriculum for England and Wales and in-depth and up to date knowledge and understanding of examination boards requirements.
• Successful experience with inclusion and assessment leadership and development.
• A clear understanding of the teaching and learning processes, recent developments in education and of the factors and strategies that can impact upon student performance.
• A clear understanding and experience of Child Protection and Safeguarding policy and procedures.
• Knowledge and successful experience of budget preparation, management and reporting procedures and personnel leadership and management.
• Excellent organisation and communication.
• High level of personal integrity and confidentiality.
• Think strategically, analytically and creatively.
• Outstanding interpersonal skills with the ability to work collaboratively
• Ability to work independently, multitask, manage multiple priorities, and meet deadlines.
• Proficient in the use of Microsoft Office Products and Management Information Systems.

Salary range for the position listed above is CI$74,000.00 – CI$86,000.00 per annum commensurate with experience based on the school’s point salary scale.  Benefits include:

• 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
• Tax free salary
• Generous school holidays
• Continued Professional Development Opportunities throughout the School Year

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

APPLICATIONS WILL ONLY BE CONSIDERED IF SUBMITTED ON THE RELEVANT SCHOOL APPLICATION FORM and submitted along with a cover letter and CV. 

Applicants must apply using this link – https://wkf.ms/4tPLYTi

The cover letter should be addressed to:

Mr. Karl Murphy, High School Principal

P.O. Box 10013

Grand Cayman KY1-1001

Cayman Islands

For further information about all job vacancies and how to apply please use this link – www.cayprep.edu.ky/about-cphs/vacancies/

Deadline for receipt of applications: Tuesday, June 2^nd, 2026

Only shortlisted candidates will be contacted.