Vice President of Operations

Caribbean Resort & Villas

$120K — $150K *
Hospitality & Recreation
11 - 15 years of experience
Job Overview by Ladders

Qualifications

  • 15+ years of leadership experience in hospitality operations overseeing multiple properties.
  • Ability to work effectively in shared-ownership environments like condo-hotels.
  • Proven success in developing high-performing teams through mentorship and accountability.
  • Preferred Florida Community Association Manager (CAM) license or similar certification.
  • Familiarity with condominium governance and HOA structures preferred.
  • Demonstrated experience managing operations with consistency in performance across locations.
  • Strong business judgment and capacity for navigating competing priorities.

Responsibilities

  • Provide strategic direction to property leadership teams as a trusted partner.
  • Strengthen leadership capability by identifying and nurturing high-potential talent.
  • Reinforce a culture of accountability and service excellence across all properties.
  • Maintain professional relationships with ownership and external partners.
  • Oversee leadership performance through goal alignment and coaching.
  • Direct operational performance to ensure consistency in service delivery across the portfolio.
  • Monitor performance trends and implement improvements to enhance asset value.

Benefits

  • Weekly pay for all team members.
  • Medical and Dental insurance options.
  • Supplemental insurance plans available.
  • Paid Time Off (PTO) for employees.
  • 401(k) retirement plan with company match.
  • Employee Assistance Program for support services.
  • Tuition reimbursement for continuing education.
  • Resort accommodations discounts for employees.
Full Job Description
Overview

The Vice President of Operations provides strategic oversight for a diverse portfolio of hospitality assets, including condo-hotel properties, with a focus on delivering strong operational and financial performance. This role is accountable for creating alignment across guest service, employee engagement, and owner relations while supporting sustainable business growth.

Partnering with on-property leadership teams, the Vice President ensures effective execution of company standards, fosters leadership development, and drives accountability across all areas of operation. This position requires a strong understanding of the condo-hotel environment, balancing the needs of individual owners with overall operational goals. By leading portfolio-wide initiatives, this executive enhances efficiency, strengthens service delivery, and maximizes long-term asset value.

Responsibilities

Vice President of Operations responsibilities include, but are not limited to:

Executive Leadership & Talent Development
  • Provide strategic direction and guidance to property leadership teams, serving as a trusted partner to General Managers and senior leaders across multiple locations.
  • Strengthen leadership capability by identifying, developing, and retaining high-potential talent, while supporting succession planning and long-term organizational growth.
  • Reinforce a culture centered on accountability, service excellence, and collaboration, ensuring alignment with company values across all properties.
  • Maintain strong, professional relationships with ownership groups, HOA/board members, and external partners, acting as a senior representative of the organization.
  • Oversee leadership performance, including goal alignment, coaching, and performance improvement planning as needed.
  • Lead executive-level evaluations for property leaders, aligning development priorities with business objectives.

Operational Strategy & Portfolio Oversight
  • Direct day-to-day operational performance across a portfolio of hotels and resorts, ensuring consistency in service delivery, operational standards, and overall experience.
  • Monitor performance trends across properties, identifying opportunities to improve efficiency, increase participation in rental programs, and enhance asset value.
  • Step in to support or stabilize operations when needed, including guiding turnaround efforts and strengthening leadership structures.
  • Conduct regular on-site visits and operational reviews to assess performance, reinforce expectations, and drive accountability.
  • Facilitate ongoing communication with property leaders through structured meetings focused on key metrics, priorities, and strategic initiatives.
  • Establish and refine operating processes and systems to support scalability, consistency, and operational effectiveness.
  • Partner with corporate teams such as Sales, Finance, HR, and Revenue Management to ensure alignment and execution of company-wide initiatives.
  • Provide oversight for cross-functional projects, ensuring timelines, accountability, and results are achieved.
  • Travel regularly to support portfolio needs, stakeholder engagement, and operational oversight.

Financial & Asset Performance
  • Hold overall responsibility for financial outcomes across the portfolio, including budgeting, forecasting, and profitability.
  • Collaborate with finance and revenue teams to strengthen revenue strategies, improve key performance metrics, and maximize returns.
  • Guide labor planning and cost controls while maintaining service standards in a dynamic operating environment.
  • Partner with property leaders to execute financial plans that meet company goals and stakeholder expectations.
  • Lead financial discussions with ownership and board representatives, providing clear updates on performance, forecasts, and action plans.
  • Support capital planning efforts, ensuring investments align with operational needs, guest expectations, and long-term asset value.

Qualifications

What are we looking for?
  • Extensive leadership background (typically 15+ years) within hospitality operations, including oversight of multiple properties or complex portfolios.
  • Experience working in shared-ownership environments such as condo-hotels-or the ability to quickly adapt to similar operational models-balancing guest experience, owner engagement, and program performance.
  • Strong track record of building, leading, and developing high-performing teams through coaching, mentorship, and accountability.
  • Florida Community Association Manager (CAM) license or similar certification preferred.
  • Familiarity with condominium governance, HOA structures, and related regulatory considerations preferred.
  • Demonstrated success managing operations across multiple locations, ensuring consistency in performance, service delivery, and operational standards.
  • Solid business judgment with the ability to navigate competing priorities and make informed decisions in a fast-moving environment.
  • Excellent interpersonal and communication skills, with the ability to effectively engage and influence senior leaders, ownership groups, and board members.
  • Highly organized with a focus on execution, capable of managing multiple priorities while maintaining attention to detail and alignment with broader goals.
  • Self-motivated leader who takes ownership of outcomes and drives results with a sense of urgency.
  • Comfortable operating in evolving environments, with the ability to adjust quickly and lead through change and complexity.
  • Willingness to travel as needed to support portfolio operations and stakeholder engagement.
  • Prior experience as a Hotel or Resort General Manager required; broader regional or multi-property leadership experience preferred.
  • Exposure to disciplines such as Sales, Revenue Management, or asset strategy is preferred.
  • Flexibility to work a schedule that may include evenings, weekends, and holidays in alignment with business demands.


What can you look forward to?

All team members enjoy WEEKLY PAY!

Qualifying team members may enjoy the following benefits:
  • Medical and Dental insurance
  • Supplemental insurance plans (ex. Vision, Life, etc...)
  • Paid Time Off
  • 401(k) retirement plan with company match
  • Bereavement Leave
  • Jury Duty Pay
  • Employee Assistance Program
  • David L. Brittain Scholarship Program
  • Tuition Reimbursement
  • Resort Accommodations Discount
  • And more!


Similar Jobs

More Jobs at Caribbean Resort & Villas

More Hospitality & Recreation Jobs

Find similar Vice President of Operations jobs: