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