Director of Operations, Caribbean

This role sets operational standards, builds high-performing teams, drives continuous improvement, and partners with commercial, finance, and people teams to deliver exceptional guest experiences and sustainable growth.

Director of Operations, Caribbean 

 The Director of Operations is responsible for leading multi-site, multi-service operations across the Caribbean. Ensuring safe, compliant, guest-ready, and financially disciplined delivery of Marine Division activities, ground transportation, product development, and tour desk operations across Jamaica & the Northern Caribbean.

Responsibilities:
Operational Leadership (All Locations)

• Own day-to-day operational performance of the tour desk across Jamaica, Turks and Caicos, and The Bahamas, ensuring consistent service standards and execution.
• Develop and maintain operating procedures, checklists, and training programs to ensure consistent, scalable delivery.
• Oversee day-to-day business operations across all departments
• Establish KPIs and operating rhythms (daily/weekly reporting, site reviews, incident reviews) to monitor safety, service quality, on-time performance, and profitability.
• Lead workforce planning, scheduling, and coverage models aligned to demand forecasts and seasonal peaks.
• Partner with Finance/HR to manage budgets, labour controls, and unit economics; identify and deliver cost optimization without compromising safety or guest experience.
• Drive vendor and contract management for critical suppliers (marinas, fuel, maintenance, vehicle service, third-party tour operators), including SLAs and performance reviews.
• Ensure compliance with local regulations and company policies; maintain required licenses, permits, and records for each jurisdiction.
• Serve as escalation point for guest issues and operational disruptions; coordinate rapid recovery plans and communications.

Marine Division

• Oversee all marine operations, including vessel readiness, dock operations, crew standards, dispatch, and guest boarding processes.
• Implement a preventive maintenance program for vessels and marine equipment; ensure documentation, inspections, and defect tracking are current.
• Ensure marine safety management practices, including risk assessments, weather/sea-state protocols, emergency drills, and incident reporting.
• Manage captains/crew staffing, training, certifications, and performance; build a culture of safety and professionalism.
• Coordinate with marinas, port authorities, and local regulators to maintain compliance and operational access.
• Monitor fuel usage, parts inventory, and maintenance spend; optimize utilization and downtime to maximize availability and revenue.
• Lead a marine management team.

Transportation

• Standardize fueling, parts, and consumables controls; monitor shrinkage and enforce purchasing/approval protocols.
• Lead transportation operations across all destinations, including dispatch, routing, airport/port transfers, and tour-related ground logistics.
• Ensure fleet readiness through preventive maintenance, inspections, cleanliness standards, and replacement planning.
• Manage driver recruiting, onboarding, training, scheduling, and performance; ensure required licenses and records are maintained.
• Improve on-time performance and guest communications through strong dispatch controls and real-time issue resolution.
• Oversee transportation vendor partnerships as needed; negotiate rates and service standards, and monitor performance.

Fleet & Asset Management

• Maintain complete asset registers for vessels, vehicles, and critical equipment by destination, including age, hours/mileage, service history, and replacement timelines.
• Set fleet availability targets and preventive maintenance standards; coordinate maintenance windows to protect capacity during peak demand.
• Implement daily readiness checks (safety gear, cleanliness, mechanical condition) and defect tracking with clear out-of-service criteria.
• Oversee replacement planning and capital requests (CapEx), including total cost of ownership and ROI justification.

Qualifications:

• 10+ years of progressive operations leadership experience in tourism, hospitality, marine, transportation, or multi-site service operations.
• Minimum of a Bachelors Degree in business administration, operations management, or a related field.
  
• Demonstrated experience managing safety, compliance, and regulated operations (marine and/or commercial transportation preferred).
• Strong financial acumen with experience managing budgets, labor controls, and vendor contracts.
• Proven ability to lead diverse teams across multiple locations and build scalable processes.
• Proficiency with scheduling, reservation/booking, and reporting systems; advanced Excel/Google Sheets skills preferred.
• Valid driver’s license; ability to obtain/maintain any destination-specific clearances, permits, and credentials required for the role.

Core Competencies:

• Safety leadership and sound operational judgment.
• Guest-first mindset with strong service recovery skills.
• Data-driven decision-making and KPI management.
• Process design, standardization, and continuous improvement.
• Clear communication across cultures and stakeholder groups.
• Strong organization, prioritization, and crisis management.
• Vendor negotiation and relationship management.

Work Schedule & Travel:

• Requires flexibility to work weekends/holidays and adjust hours to operational demand and peak season.
• Regular inter-island and international travel across Jamaica, Turks and Caicos, and The Bahamas as required.
• May require on-call availability for operational escalations, severe weather events, and service disruptions.

Please note: Only shortlisted candidates will be contacted. Thank you for your application.