Deputy CEO

thehivecareers.co; San Juan (PR); On-site; USD 180,000 - 300,000; Full time

Job summary

The Hive Careers is seeking a Deputy Chief Executive Officer to accelerate growth, optimize profitability and lead regional expansion in Jamaica and the wider Caribbean. Based in San Juan, you will partner with the CEO to translate strategy into measurable results.

You will drive revenue through enterprise sales, strategic partnerships and market development, while owning P&L and overseeing key functions to scale operations and performance.

Qualifications

• 10+ years of progressive senior leadership experience in general management or related areas.
• Proven ownership of P&L, revenue and profitability targets.
• Experience growing businesses, markets or service lines with enterprise clients.

Responsibilities

• Partner with the CEO to execute the company's strategic and commercial priorities.
• Drive revenue generation through business development, enterprise sales and partnerships.
• Protect existing revenue via client retention and contract oversight.
• Lead cost optimization and operational efficiency to improve margins.
• Provide executive oversight of Sales, Operations, Talent Delivery and other key functions.
• Own and monitor P&L, budgets, forecasts, margins and KPIs.
• Strengthen enterprise client relationships and lead high-level negotiations.
• Identify new markets, services and revenue opportunities across Jamaica and the wider Caribbean.
• Drive scalable processes, technology adoption, automation and performance management.
• Build and develop high-performing leadership teams.
• Identify risks and ensure mitigation strategies are implemented.
• Provide strategic insights to support sustainable growth.

Skills

Senior leadership

P&L ownership

Revenue generation

Strategic planning

Cost optimization

Stakeholder management

Multi-country leadership

Partnerships

Operations leadership

Staffing experience

Job description

About the Job - Deputy CEO

The Hive Careers is seeking a commercially driven and execution-focused Deputy Chief Executive Officer (Deputy CEO) to support the CEO in driving business growth, financial performance, operational excellence and regional expansion.

This is a senior executive role requiring a leader who can translate strategy into measurable business results, with a strong focus on revenue generation, revenue protection, profitability and cost optimization.

Key Responsibilities

• Partner with the CEO to execute the company's strategic and commercial priorities.
• Drive revenue generation through business development, enterprise sales, strategic partnerships and market expansion.
• Protect existing revenue through strong client retention, account management, contract performance and commercial oversight.
• Lead cost optimization and operational efficiency initiatives to improve margins and profitability.
• Provide executive oversight of Sales, Operations, Talent Delivery and other key business functions.
• Own and monitor P&L performance, budgets, forecasts, margins and key business KPIs.
• Strengthen enterprise client relationships and lead high-level commercial negotiations.
• Identify new markets, service offerings and revenue opportunities across Jamaica and the wider Caribbean.
• Drive scalable processes, technology adoption, automation and performance management.
• Build and develop high-performing leadership teams.
• Identify business, financial and operational risks and ensure appropriate mitigation strategies are implemented.
• Provide strategic insights and recommendations to the CEO to support business decisions and sustainable growth.

Required Experience

• 10+ years of progressive senior leadership experience in general management, commercial leadership, operations, consulting, staffing, HR technology, B2B services or related areas.
• Proven ownership of P&L, revenue and profitability targets.
• Demonstrated success in generating and protecting revenue while optimizing costs.
• Strong track record of growing businesses, markets, teams or service lines.
• Experience managing enterprise clients, strategic partnerships and executive-level stakeholders.
• Strong commercial, financial, strategic and operational acumen.
• Experience leading multiple business functions and senior teams.
• Staffing, outsourcing, consulting or workforce solutions experience is preferred.
• Caribbean, regional or multi-country leadership experience is an advantage.

Who We're Looking For

A commercially strong, strategic and execution-driven executive who can operate as a trusted partner to the CEO while taking ownership of business performance.

The ideal candidate brings a strong track record of growing revenue, protecting profitability, optimizing costs and scaling businesses, combined with the leadership presence and accountability required to help drive The Hive Careers' next phase of growth.