Demo

Sales Director- Cloud & Managed Services

Cloud Carib Limited
Miami, FL Full Time
POSTED ON 11/11/2025
AVAILABLE BEFORE 5/9/2026

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 

 

 

Compensation & Benefits 

A competitive compensation package will be offered, including base salary, performance-based incentives, and regional travel allowances. 

 

Salary.com Estimation for Sales Director- Cloud & Managed Services in Miami, FL
$175,175 to $232,465
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