Caribbean American Alliance (CAA) is seeking a highly disciplined, execution-driven Project Manager Lead to oversee and deliver multiple strategic initiatives across the organization. This role is responsible for managing end-to-end project execution, ensuring deadlines are met, stakeholders remain aligned, and revenue-generating deliverables are completed on time and within scope. The Project Manager Lead will play a critical role in organizing internal teams, vendors, partners, and contractors to drive measurable outcomes. The ideal candidate is structured, proactive, detail-oriented, and capable of leading complex projects with minimal supervision. This position includes a base salary plus commission incentives tied to successful project execution and revenue generation. This is a hands-on role within a lean, entrepreneurial team. You'll be working closely with a small group of dedicated professionals where every team member wears multiple hats and contributes directly to organizational success. The ability to work independently while collaborating effectively in a close-knit environment is essential. Key Objectives of the Role The Project Manager Lead is expected to:
Drive the successful execution of all assigned CAA strategic projects.
Establish clear project structures, timelines, and accountability frameworks.
Identify and resolve project risks before they impact delivery.
Support revenue growth by ensuring projects deliver financial impact.
Reporting Structure
Reports directly to: CEO
Works closely with: Leadership. In a small team environment, you'll work directly with leadership and team members across all functions, often managing projects where you're the primary driver coordinating multiple stakeholders.
Key Responsibilities 1. Project Planning and Execution
Lead the full project lifecycle from concept to completion.
Create detailed project plans including:
Scope of work
Objectives and expected outcomes
Timeline and milestones
Required resources
Budget framework
Execution strategy
Ensure each project has defined deliverables, deadlines, and accountability.
Ensure all projects align with CAA’s strategic priorities and mission.
Track all project progress using structured tools (Asana, Monday, etc.).
2. Stakeholder and Team Management
Coordinate all internal teams and external stakeholders involved in projects.
Conduct weekly check-ins with project contributors and provide task follow-ups.
Facilitate productive project meetings with clear agendas and action items.
Ensure project participants remain aligned and informed at all times.
Communicate clearly with leadership regarding project risks, needs, and bottlenecks.
3. Weekly Reporting and Performance Tracking The Project Manager Lead must provide structured weekly progress reporting to leadership. Provide concise weekly progress reports to leadership covering: · Project status dashboard (Green/Yellow/Red by initiative) · Completed work, upcoming priorities, and blockers · Budget tracking and resource needs · Revenue impact and risk mitigation updates The role requires strong discipline in documentation and reporting. Leadership must always have visibility on project execution status. 4. Budget Oversight and Vendor Coordination
Support project budgeting and cost forecasting.
Track project expenses and ensure spending remains within approved limits.
Manage relationships with vendors, contractors, and third-party service providers.
Ensure vendor deliverables are completed on time and meet CAA standards.
Review and validate invoices, vendor quotes, and service agreements.
Work with Finance to ensure proper payment schedules and contract compliance.
5. Revenue-Generating Project Leadership CAA’s Project Manager Lead must ensure revenue-driven projects deliver measurable financial results. This includes:
Managing implementation of partnership agreements
Supporting the delivery of distribution deals and commercial programs
Coordinating event execution and sponsorship initiatives
Monitoring project ROI and reporting on revenue performance
The Project Manager Lead must understand how project execution impacts revenue and profitability. 6. Business Process Improvement
Create repeatable systems for project execution across the organization.
Develop templates and SOPs for:
Project kickoff process
Weekly reporting format
Risk assessment tracking
Vendor onboarding
Post-project evaluation
Build a structured “CAA Project Execution Playbook” to improve efficiency.
Implement a centralized project tracker across all departments.
7. Risk Management and Quality Control
Identify project risks early and implement corrective actions.
Maintain a risk register for all active projects.
Ensure quality standards are met for all deliverables.
Ensure compliance with deadlines and contractual obligations.
Ensure project documentation is organized and stored properly.
8. Cross-Functional Collaboration The Project Manager Lead will collaborate across multiple business units, including:
CAA Distribution and Trade Programs
Caribbean Xpress and logistics-related partnerships
Government and institutional partnerships
Digital transformation initiatives
Community outreach programs
Events and sponsorship execution
Corporate partnership development programs
The role requires flexibility and the ability to manage multiple projects simultaneously. In a small team environment, you'll work directly with leadership and team members across all functions, often managing projects where you're the primary driver coordinating multiple stakeholders. Key Projects the Role May Oversee In a small team setting, you may be the sole project manager driving multiple initiatives simultaneously. Examples include:
Launch of new regional distribution partnerships
Execution of merchant acquisition campaigns
Project management for technology and platform rollouts
CAA-led conferences, investment forums, and cultural events
Vendor onboarding and contract execution for major partnerships
Market entry planning and execution for new territories
Coordination of community development initiatives
Required Skills and Competencies Core Skills
Strong project planning and execution skills
Ability to manage multiple projects at the same time
Strong time management and prioritization ability
Excellent organizational skills and follow-through
Strong written communication and reporting skills
Strong ability to manage deadlines and hold teams accountable
Vendor negotiation and coordination experience
Budget tracking and cost management capability
Leadership and Behavioral Competencies
Self-disciplined and able to work independently without daily supervision
High accountability and ownership mindset
Ability to work under pressure and manage competing priorities
Strong decision-making skills
Professional communication style with internal teams and external partners
Strong problem-solving and conflict resolution skills
Ability to drive results with urgency
Preferred Qualifications
Bachelor’s degree in Business, Project Management, Operations, Finance, Marketing, or related field (preferred)
Project Management certification (PMP, CAPM, Prince2) is a plus
Minimum 5 years’ experience in project management or operations leadership
Experience working with cross-border initiatives, government agencies, or corporate partnerships is a strong advantage
Experience working in the Caribbean or with diaspora-driven initiatives is preferred
Strong knowledge of Microsoft Office (Excel, PowerPoint, Word) required
Tools and Technology Requirements The candidate should be comfortable working with:
Project management tools: Monday.com, Asana, Trello or ClickUp
Google Workspace or Microsoft Office Suite
Excel project trackers and dashboards
Zoom / Microsoft Teams meeting coordination
CRM tools (preferred)
Reporting dashboards and KPI monitoring
Compensation Structure Base Salary
Competitive base salary based on experience and performance.
Commission / Performance Incentives The Project Manager Lead will receive commissions tied to:
Successful completion of revenue-generating projects
Execution of projects that lead to signed contracts
Delivery of projects that result in measurable revenue growth
Achievement of agreed quarterly project KPIs
Commission structure will be determined based on the nature of each project and the revenue generated. Specific commission rates and project eligibility will be discussed during the interview process and defined in your employment agreement. Performance Metrics (KPIs) Performance will be evaluated based on:
On-time project completion rate
Weekly reporting compliance and accuracy
Quality of project deliverables
Revenue impact of executed projects
Budget compliance and cost control
Stakeholder satisfaction and communication effectiveness
Ability to identify and resolve project blockers quickly
Implementation of operational systems and SOPs
Work Schedule and Location
Part-time position
Flexible schedule expected, with high availability during project launches
Travel may be required depending on project location to include Florida, Caribbean markets, and international partner locations
Hybrid or remote work may be acceptable depending on candidate location
Candidate Profile (Ideal Fit) The ideal Project Manager Lead is:
Highly organized and structured
Action-oriented and execution-driven
Comfortable holding others accountable
Skilled at managing timelines and budgets
Strong communicator with leadership presence
Able to deliver under pressure
Comfortable working with multiple cultures and international partners
Focused on results, not activities
Application Requirements Applicants should submit:
Resume
Short cover letter explaining project management experience
Examples of project plans, trackers, or reporting templates previously used.
Email applications to [email protected] Email subject : Project Management Lead