Cayman International School (CIS) is seeking a highly organized, discreet, and proactive Executive Assistant to the School Director to provide executive-level administrative support in a dynamic, mission-driven international school environment. This role serves as a trusted partner to the School Director, supporting the strategic and operational priorities of the Director’s Office. The Executive Assistant acts as a key point of coordination between the Director, senior leadership, faculty, staff, parents, and external stakeholders. The position requires sound judgment, exceptional attention to detail, and the ability to manage confidential information with the highest level of professionalism. The ideal candidate is adaptable, calm under pressure, highly organized, and enjoys working in a fast-paced school setting where priorities shift quickly. Title / Role Executive Assistant to the Director Role Requirements
The successful candidate is required to have the following
Bachelor’s degree preferred, or equivalent.
Minimum 3–5 years’ experience in an executive-level or senior administrative support role, preferably supporting senior leadership in a school environment.
Valid Cayman Islands driver’s licence and ability to run occasional off-site errands.
Proven track record of excellence at current and previous places of service.
Notary Public status is an asset.
Core Skills & Competencies
Demonstrated ability to handle highly sensitive and confidential information with discretion and professionalism. Excellent written and verbal communication skills, with the ability to interact effectively with parents, staff, students, and external stakeholders.
Strong customer service orientation, maintaining a welcoming and professional presence at all times.
Strong project coordination and organizational skills.
Advanced organizational and time-management skills, with the ability to manage multiple priorities in a fast-paced school environment.
Ability to anticipate needs and proactively support the priorities of the Director and the Director’s Office.
High level of attention to detail and accuracy in documentation and communications.
Strong problem-solving skills and the ability to exercise sound judgment and initiative.
Ability to exercise sound judgment in prioritizing issues and determining when matters should be elevated to the Director.
Proficiency in Microsoft Office Suite (Word, Excel, Outlook, PowerPoint) and Google Workspace (Docs, Sheets, Slides, Calendar, Gmail); experience with school management systems, communication platforms, or scheduling tools is an asset.
Excellent typing and document formatting skills.
Ability to work independently.
Strong interpersonal skills and cultural awareness when working in a diverse, international community.
Ability to lift up to 25–30 lbs occasionally (files, event materials, supplies).
Understanding of and appreciation for working within a student-centered school environment.
Occasional evening or weekend work may be required to support school events, meetings, or Director-related functions.
Cayman International School provides a comprehensive array of incentives and benefits tailored to the role. Here's an overview:
Health Insurance: (100% coverage of the SHIC Plus 250 premium plan) and contribution to higher plans if elected
38 Annual Vacation days in a calendar year
Wellness Benefit: A one-time annual benefit of $500
Travel Allowance: A one-time annual benefit of $1,000
Telephone Allowance: Up to $500 (conditions apply)
Professional Development: Up to $1,000 allocated annually
Tuition Benefit: after completing three years of employment, you may be eligible to enroll your dependent child(ren) in the High School, specifically grades nine through twelve, provided they meet CIS admission requirements. The tuition waiver for dependent children who reside with you full-time while you are employed at the school is outlined below:
o First Child: 100% tuition waiver o Second Child: 50% tuition waiver o Third Child: 20% tuition waiver
Years of Service Benefit: Varies depending on milestone anniversary date
