Job Title: Executive Assistant to the CEO (High-Impact / Strategic EA)

Company: Caribbean Online Academy | South East College | Omnicare Pharmacy
Reports to: Chief Executive Officer (CEO)
Location: Mandeville, Jamaica (On-site)
Work Hours: Full-time (flexible schedule required; occasional evenings/weekends)

Role Summary

We are seeking a high-impact Executive Assistant (EA) to work directly with the CEO across three dynamic, growing entities: This role is ideal for a trusted right-hand professional who brings structure, leadership, and exceptional people support in a fast-paced, mission-driven environment.

This is not a basic administrative role. The successful candidate will operate as a strategic partner—driving execution, improving systems, protecting the CEO’s time, and ensuring priorities move forward with speed and accuracy. You must be comfortable acting with confidence on behalf of the CEO when needed, while exercising sound judgment, discretion, and professionalism.

Key Outcomes for Success (What “Excellent” Looks Like)

The CEO’s time is protected, priorities are clear, and decisions move quickly.
Meetings are purposeful, well-prepared, and result in measurable follow-through.
Communication across teams is smoother, faster, and more consistent.
Students, parents, staff, and external stakeholders experience exceptional service.
Internal operations become more structured with improved tracking, reporting, and accountability.
Culture is supported through strong communication, relationship-building, and problem-solving.

Core Responsibilities

1) Executive Support & CEO Office Management

Serve as the CEO’s primary point of contact and gatekeeper, managing requests with tact and urgency.
Manage the CEO’s calendar across multiple businesses: scheduling, prioritizing, and reducing time conflicts.
Prepare the CEO for all meetings (agendas, briefing notes, stakeholder context, documents, key questions).
Take high-quality meeting minutes and translate discussions into clear action items with owners and deadlines.
Coordinate executive travel, events, and logistics (as required).
Handle confidential matters with discretion, professionalism, and sound judgment.
Proactively anticipate needs—identify risks, solve problems, and bring options/solutions (not just updates).

2) Strategic Execution & Project Coordination

Drive execution on CEO priorities across the Academy, College, and Pharmacy—ensuring plans turn into outcomes.
Build lightweight systems for tracking initiatives (project trackers, dashboards, weekly action reviews).
Coordinate cross-functional projects (e.g., enrollment initiatives, academic operations, pharmacy service upgrades).
Follow up with managers and team leads to ensure tasks are completed on time and to standard.
Support operational improvements by documenting processes (SOPs), simplifying workflows, and improving structure.
Maintain a “CEO Priorities” pipeline and ensure timely progress reporting.

3) Communication & Stakeholder Management

Draft and send professional communications on behalf of the CEO (internal and external).
Ensure communication is consistent across students, parents, staff, partners, and vendors.
Support customer service excellence by identifying recurring issues and implementing improvement actions.
Act as a liaison between the CEO and leadership/team members—ensuring clarity and accountability.
Support crisis-sensitive communication with empathy and accuracy (especially in education and pharmacy settings).

4) People Support & Culture Protection

Support a positive, high-performance culture by modeling professionalism, care, and accountability.
Assist with onboarding, staff engagement, internal communication, and employee coordination activities.
Help ensure staff follow agreed processes, standards, and service expectations.
Support conflict resolution and relationship-building by listening, clarifying issues, and escalating appropriately.
Coordinate recognition initiatives, staff check-ins, and culture-building activities in partnership with leadership.
Protect the CEO’s leadership “voice” by ensuring consistent follow-through and respectful communication.

5) Representation & Leadership on Behalf of the CEO

Represent the CEO in meetings when needed, provide updates, and carry decisions back to the team.
Lead select meetings, follow-ups, and coordination efforts to ensure execution continues in the CEO’s absence.
Build trust across teams while maintaining boundaries, confidentiality, and professionalism.

6) Systems, Tools & Administrative Excellence (Done at a High Level)

Manage files, documentation, templates, records, and standard communication formats.
Maintain accurate digital organization: shared drives, folders, naming conventions, and document control.
Use technology tools to increase productivity and visibility (e.g., Google Workspace/Microsoft 365, Slack/Teams, Zoom, Asana/Trello/ClickUp, CRM/Student Information Systems, ticketing tools).
Create and maintain reports and dashboards (weekly summaries, KPI trackers, action registers).

Required Competencies & Attributes

We’re looking for someone who is:

Passionate about education and student-centered service
Customer-obsessed—excellent service for students, parents, staff, and stakeholders
Highly tech-savvy and confident using digital tools and systems
Extremely organized, detail-oriented, and strong at building structure
Adaptable and flexible, comfortable managing a dynamic executive schedule
Emotionally intelligent—calm under pressure, tactful, professional, and people-oriented
A confident leader who can represent the CEO appropriately and decisively
Discreet and trustworthy, able to manage sensitive information
Proactive and solution-driven, able to think ahead and execute without being micromanaged
Committed to growth, excited to develop into a long-term strategic support role

Qualifications & Experience

Minimum 3–5 years of experience in an Executive Assistant, Senior Administrative, Operations Coordinator, or Chief of Staff support role (preferred).
Experience supporting senior leadership in a fast-paced environment.
Strong writing and communication skills (email, reports, meeting briefs, internal memos).
Strong planning and coordination ability across multiple priorities.
Experience in education, healthcare/pharmacy, customer service operations, or regulated environments is an asset.
Strong proficiency in digital tools (Google Workspace/Microsoft 365, calendars, spreadsheets, project tools).

Performance Indicators (KPIs)

Calendar efficiency and reduced scheduling conflicts
Meeting effectiveness (agendas, action items, completion rate, follow-through)
On-time completion of CEO priority projects and deliverables
Stakeholder satisfaction (students/parents/staff responsiveness and resolution quality)
Quality of documentation, reporting, and internal communication
Improved structure and reduced operational “chaos” through systems and process improvements

Working Style & Expectations

High accountability and consistent follow-through
Comfortable with ambiguity and fast change
Quick response times during business hours and for urgent matters
Able to maintain professionalism while working across education and pharmacy environments
Willing to handle both strategic and hands-on tasks when needed

Executive Assistant to The CEO