Island Routes - Director of Operations, Caribbean
Montego Bay, St. James, Jamaica
Full Time
Retail and Hospitality
Executive
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. 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.
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.
- 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.
- 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.
- 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.
- 10+ years of progressive operations leadership experience in tourism, hospitality, marine, transportation, or multi-site service operations.
- Minimum of a Bachelor's 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.
- 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.
- 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.
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