Guest Experience Manager (Remote in South America)

About Bocobay

Bocobay is revolutionizing hospitality through innovative, tech-powered service and inspiring, thoughtfully designed accommodations combined into one seamlessly managed experience. Launched in 2020 in Aruba, Bocobay is a fast-growing business bringing a new standard to the Caribbean vacation rental market. We now operate across four islands — Aruba, Curaçao, the Dominican Republic and Jamaica — and we have ambitious plans to continue expanding across the Caribbean. 

Our guests are at the heart of everything we do. A five-star experience doesn't happen by chance: it is the product of fast, thoughtful communication, well-coordinated operations, and a team that genuinely cares. As we scale, we need an exceptional leader to own this end of the business.

The Role

As Guest Experience Manager you will own everything related to guest communications and satisfaction at Bocobay. You will be the escalation point for complex guest situations, the manager and coach of our distributed guest communications team, and the person responsible for continuously raising the bar on how we communicate with guests. 

This is a senior individual-contributor and people-management hybrid role. You will report directly to the COO and have significant autonomy to shape how guest communications works at Bocobay.

Key Responsibilities

Team Leadership & Management

• Hire, onboard, train and manage a team of guest communications agents (currently a group of remote contractors).
• Create a high-performance culture within the team: set clear expectations, run regular 1-to-1s, and build a motivated, reliable crew.
• Work closely with the Quality Assurance lead to improve team performance. 
• Manage scheduling and coverage to ensure guests always receive fast responses, including during peak periods and weekends.
• Identify strong performers and nurture their growth within the company.

Guest Escalations

• Serve as the escalation point for difficult guest situations — unhappy guests, complex complaints, potential negative reviews.
• Make fast, sound judgement calls on resolutions (refunds, gestures of goodwill, escalation to island GMs) that protect both the guest relationship and Bocobay's commercial interests.
• Follow up diligently to ensure issues are resolved end-to-end, and that learnings are captured and fed back into processes.

Documentation & Process Improvement

• Own and continuously improve the guest communications handbook and wiki — the primary reference resource for all agents.
• Identify gaps and recurring issues in how we communicate with guests, and design better responses, templates and workflows.
• Work closely with operations teams on the ground to improve the feedback loop between guest issues and operational fixes.
• Track and report on key metrics: response times, guest satisfaction scores, review outcomes and team productivity.

What We Look For

• 5+ years in a guest-facing hospitality or customer experience role, with at least 2 years managing a team.
• Native or near-native fluency in both English and Spanish — you will communicate with guests and team members in both languages every day.
• Exceptional verbal and written communication skills: you can deliver a message that is warm, clear and on-brand under pressure.
• Strong people manager: you know how to build trust with a distributed team, give constructive feedback and drive performance.
• Highly organised with excellent follow-through — nothing falls through the cracks on your watch.
• Comfortable with ambiguity and fast-paced environments; you thrive when things are changing and you can help shape how they evolve.
• Familiarity with vacation rental or OTA platforms (Airbnb, Booking.com, Expedia) is a strong plus.
• Experience with tools such as Hostaway, Breezeway, Conduit or similar PMS/CRM platforms is a plus.
• A genuine passion for hospitality and delivering exceptional guest experiences.

Important to Note

We are a young, fast-growing company and this is not a strictly 9-to-5 role. Guest issues don't keep office hours, and you will need to be reachable and responsive during peak periods, including some evenings and weekends. This is balanced by flexibility during quieter periods: we trust our people and encourage them to take back time when things are calm. 

This is a fully remote role, but occasional travel to Caribbean islands may be required. You will work closely with our COO (based in London), our island operations teams across the Caribbean, and a distributed guest communications team based in the Philippines and beyond. Strong asynchronous communication skills are essential.

Why Bocobay?

• A rare opportunity to own and build a function from the ground up in a high-growth startup.
• Direct access to senior leadership and real influence over how the company evolves.
• A company that genuinely invests in its people — we promote from within and back those who show initiative.
• Competitive compensation.