Job Description
Confidential Search: VP, Finance / Hotel Controller (Caribbean – On-Site)
A well-capitalized ownership group is seeking a hands-on finance leader to strengthen and lead the financial operations of a mid-sized full-service hospitality asset in the Caribbean.
This is a high-impact role for someone who thrives in building structure, driving accountability, and leading change in a complex, high-volume operating environment.
Why This Role
This opportunity offers a unique combination of professional challenge and lifestyle. You will play a central role in elevating the finance function of a dynamic hospitality operation while living and working in a highly desirable location.
The role is part of a broader portfolio, offering exposure to ownership and the opportunity to contribute to longer-term value creation initiatives.
It may be particularly appealing to professionals currently working internationally—or those seeking to do so—who are motivated by hands-on impact and operational involvement.
The Mandate
Stabilize, professionalize, and elevate the finance function—bringing discipline to accounting, clarity to reporting, and rigor to financial oversight.
Key Focus Areas
- Establish strong accounting fundamentals and a reliable month-end close
- Build consistent and decision-useful reporting
- Strengthen controls, governance, and financial visibility
- Identify and implement process improvements
- Assess, lead, and develop the finance team
- Act as the independent financial voice on-site
What You Bring
- 10+ years of progressive finance leadership experience
- Experience in hospitality, hotels, resorts, or similarly complex high-volume operations
- Strong technical accounting and hands-on capability
- Strong understanding of recognized accounting frameworks
- Track record of improving processes, controls, and reporting in under-structured environments
- CPA (or equivalent) an asset
Profile
Practical, resilient, and execution-focused. Comfortable operating on the ground, driving change, and holding the line on financial discipline.
Location
Caribbean (on-site). This role requires a high, sustained physical presence in the operation, particularly in the first 12 months. Relocation is expected.
About Caldwell
Caldwell
caldwellinc.com
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