Position Overview
The Sales Director will lead the regional sales organization for a premier Cloud and Managed Services provider serving the English-speaking Caribbean. This role is responsible for achieving company revenue objectives through effective leadership, strategic sales planning, and execution excellence. The Sales Director will manage a high-performing team of Sales Representatives across multiple countries, driving growth through both enterprise and public sector clients.
Key Responsibilities
- Leadership & Team Management:
- Lead, coach, and develop a team of 7–10 direct sales representatives operating across several countries in the English-speaking Caribbean.
- Foster a culture of accountability, collaboration, and continuous improvement within the sales team.
- Revenue & Performance Management:
- Own the regional sales quota and ensure consistent achievement of revenue targets.
- Monitor and ensure delivery on individual and team KPIs, supporting the sales team with strategy, deal structuring, and negotiations to close key opportunities.
- Sales Process Optimization:
- Review and assess the effectiveness of the sales process, identifying
bottlenecks and inefficiencies.
- Partner with Sales Operations and the Solutions team to enhance workflows, remove non-value-added tasks, and continuously improve sales velocity and conversion rates.
- Cross-Functional Collaboration:
- Collaborate closely with Sales Operations, Solutions, Client Success, and Partner Success teams to align go-to-market strategies and client engagement approaches.
- Continuously refine KPI reporting to meet Executive Management requirements and support data-driven decision-making.
- Market & Business Development:
- Develop and execute strategic plans to expand the company’s market presence in the Caribbean region.
- Build and maintain strong relationships with enterprise, government, and strategic partners to drive growth and long-term business value.
Qualifications & Experience
- Minimum of 7 years of sales management experience, with proven success leading multi-country or regional teams.
- Minimum of 5 years of direct technology sales experience, preferably in cloud computing, managed IT services, and cybersecurity solutions.
- Demonstrated success developing and closing business with enterprise and public sector clients.
- Proven ability to analyze performance data, identify improvement areas, and implement measurable action plans.
- Exceptional leadership, communication, and relationship-building skills with a collaborative and motivating management style.
- Strong strategic thinking and analytical abilities, with the capacity to balance long-term vision and short-term execution.
Preferred Attributes
- Experience working within the Caribbean or other emerging markets.
- Familiarity with subscription-based and recurring revenue business models (e.g., MRC/ARR).
- Proactive, with experience in consultative or value sales methodologies.
- Ability to thrive in a fast-paced, results-oriented environment.
- Fluent English / Spanish speaker
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What We Do
Cloud Carib is the premier provider of managed cloud services in the Caribbean and Latin American regions. Solutions range from complex bespoke dedicated private cloud offerings to hybrid cloud services. Every solution provides clients with controlled costs, unrivaled levels of service, and unparalleled levels of data protection and privacy – when and where privacy matters.
Cloud Carib’s services enable a true competitive advantage for each client that is unmatched in most of the world. Headquartered in the Bahamas, and offering multiple datacentre locations throughout the Caribbean (Freeport, Nassau, Toronto, Panama, Barbados, Jamaica and Ecuador), Cloud Carib’s solution portfolio includes: Data Centre Services, Security and Business Continuity Services, and Mobility and Productivity Offerings.
