Vice President, Commercial Caribbean

Who We Are:

As a privately held, U.S.-owned and operated company, Crowley provides services to 36 nations and island territories. Our purpose is to bravely advance what's possible to elevate people and planet, with our core values of Integrity, Sustainability and Drive guiding everything we do.

By expanding and innovating our services, we have expanded our footprint within the Logistics, Land Transportation, Shipping, and Energy industries.  Crowley and its affiliated companies have generated more than $3.5 billion in annual revenue through our people's focus on excellence and a culture that values everyone's voices and collaboration. 

To continue laying the groundwork and challenge what's possible for our business, we seek to partner with individuals ready to elevate their careers with us.

Work Arrangement:

Hybrid

What You'll Do:

The Vice President, Commercial Caribbean leads commercial execution across the Caribbean, integrating brokerage solutions to drive profitable, multimodal growth and deliver strong customer outcomes. The role provides operational and administrative leadership for the business development function, setting direction, managing processes, and ensuring disciplined execution to achieve growth objectives. The VP also provides strategic direction and operational support across the organization, along with matrixed leadership to the full Logistics Commercial team across U.S.-based and offshore locations to ensure alignment to shared goals and standards.

Key Responsibilities:

Regional Commercial Leadership & P&L Ownership

• Provide overall leadership and full P&L accountability for the Caribbean region, owning revenue growth, margin performance, and sustainable commercial profitability.
• Lead a growth ‑ first commercial agenda with a strong focus on new customer acquisition, market penetration, and expansion, while maintaining disciplined oversight of strategic account performance.
• Set clear regional commercial priorities, growth targets, and performance expectations aligned with divisional strategy, leveraging data ‑ driven insights and governance enabled through partnership with Commercial Excellence.
• Provide directional leadership to U.S. ‑ based commercial and sales teams supporting the region, ensuring execution aligns with Caribbean growth priorities and P&L objectives .

Commercial Strategy & Market Development

• Develop and execute a comprehensive regional commercial strategy centered on priority verticals, new business development, and market expansion opportunities, informed by market trends, analytics, and insights provided through Commercial Excellence.
• Align regional business development and go ‑ to ‑ market initiatives with divisional strategy, long ‑ term growth priorities, and regional operating realities.
• Prioritize high ‑ value customers, target segments, and growth opportunities to optimize profitable growth, supported by fact ‑ based segmentation, pricing discipline, and portfolio analytics.

Customer Experience & Relationship Management

• Drive a consistent, high ‑ quality customer experience across all products, services, and commercial touchpoints, ensuring growth objectives are supported by reliable execution.
• Serve as a senior commercial leader for the region, cultivating relationships with priority prospects and strategic customers while directing teams to emphasize expansion and acquisition opportunities.
• Align customers with appropriate commercial and operational resources to accelerate growth, retention, and solution optimization.

Sales Execution, Performance Management & Analytics

• Establish and oversee KPI ‑ driven commercial performance management, focusing on high ‑ impact metrics that prioritize profitable growth, pipeline quality, and new business conversion.
• Partner with Commercial Excellence to ensure forecasting, performance reporting, and commercial insights are decision ‑ ready and inform regional and senior leadership actions.
• Drive disciplined execution through pipeline management, forecasting rigor, and regular performance reviews across regional and U.S. ‑ based sales teams.

Commercial Operations, Tools & Enablement

• Drive adoption and continuous improvement of Salesforce and business intelligence tools to enhance visibility, execution discipline, and commercial effectiveness across the region.
• Ensure standardized sales processes, pricing governance, and reporting are consistently applied, leveraging frameworks and tools developed in partnership with Commercial Excellence.
• Collaborate with Marketing and Sales Operations to strengthen enablement, value messaging, and coordinated go ‑ to ‑ market execution.

Cross Functional & Global Alignment

• Lead a coordinated push ‑ pull operating model between U.S. ‑ based commercial teams and offshore P&L owners to meet customer needs and support targeted growth outcomes.
• Partner with Operations, Finance, Commercial Excellence, and other stakeholders to align commercial commitments with delivery capability, pricing discipline, and financial performance.
• Provide leadership in strategic planning, policy and process development, organizational design, and regional operating budget and performance management.

People Leadership & Organizational Effectiveness

• Lead, develop, and inspire high ‑ performing regional commercial teams through clear expectations, coaching, and accountability, with a strong emphasis on growth ‑ oriented behaviors and new business results.
• Build scalable commercial capability to support current and future regional growth, fostering a culture of continuous improvement and execution excellence.
• Model enterprise leadership behaviors by promoting accountability, engagement, and a results ‑ driven, inclusive culture.

Talent Development & Succession

• Develop leaders at all levels by building accountability, ownership, and capability; own succession planning to ensure a strong, ready leadership bench aligned to current and future business needs, with disciplined development action plans and measurable progress.
• Model and reinforce enterprise leadership expectations by driving a high performance, inclusive culture through visible leadership, strong engagement, and a consistent coaching cadence that holds leaders accountable for developing their teams and future leaders.

Experience:

10+ years management experience with a focus on commercial operations which involve an understanding of market research, sales support, analytics and forecasting which meet financial objectives. Proven experience driving strategic change, leading teams, and influencing cross-functional stakeholders.

Technical Proficiencies:

Proficient in Microsoft Office products, including Excel, Outlook and Word.

Education & Credentials:

Bachelor's degree in business, marketing or a related field; or equivalent work experience.

Other:

• Ability to travel as needed.

• This role includes additional travel expectations for candidates who are not based in Puerto Rico

• Ability to speak Spanish as a second language, strongly preferred.

What We Offer? 

We inspire top talent by offering a comprehensive and competitive package that supports the diverse needs of our people—on land, at sea, in offices, and remotely.

Our Total Rewards include:

• Competitive pay with recognition programs 
• Comprehensive benefits: medical, dental, and vision insurance, life and disability coverage, and paid vacation and holidays
• Leave and family support: parental leave and sick leave
• Learning and growth: access to training and development for continuous skill development
• Well-being resources: Employee Assistance Program, wellness program, and gym membership discounts

At Crowley, we invest in you—your success, your health, and your future.

#LI-Hybrid