Bocobay is hiring a Senior Operations Manager to work alongside our COO and take ownership of how the business actually runs day to day. You'll be the person who turns recurring problems into systems, and who makes sure our standards hold as we add islands.
About Bocobay
We're a fast growing Caribbean hospitality brand, combining modern technology with 5-star service. We are on track for $35m annual revenue in 2026 and have doubled in size every year since our launch in 2020. We now operate in Aruba, Curaçao, Jamaica and the Dominican Republic, with several new markets in the works. We're profitable and self-funded.
About the role
Part chief of staff, part head of operations. Some days you'll be designing a process; others you'll be on a guest escalation or negotiating with a supplier in Curaçao. You'll be the first call when something breaks across our islands, and the person responsible for making sure it doesn't break the same way twice.
You'll start as an individual contributor with a broad remit and a lot of autonomy. The scope grows as the company does, with a real path into senior operational leadership.
What you'll do
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Own escalations from across the islands: triage them, resolve them, and get them handled at the right level.
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Keep our operational data and systems clean and consistent across our tools (CRM, Hostaway, Breezeway, Conduit and others).
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Build and document the Bocobay operating playbook: SOPs, escalation paths, and clean handoffs between on-island teams and our global pricing, guest communications and onboarding functions.
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Work with on-island leaders and our global contractor teams to raise standards and follow-through everywhere we operate.
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Dig into why things keep going wrong and fix the cause, not the symptom.
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Get each new market operationally ready as it comes online, and mature the ones already running.
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Give the COO a clear view of what's happening operationally, and flag risks early.
What we're looking for
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You've built and improved operational systems in a fast-growing, multi-site business. Hospitality or vacation rentals is a bonus; we care more about the operator than the sector.
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You're hands-on. You'll design the system and then go clean the data yourself.
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You're a 'buck-stops-with-me' kind of person who never says 'that's not my job'.
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You're comfortable with operational numbers and can work out what they're telling you.
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You're organised and you close loops.
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You build trust quickly across cultures, teams and time zones.
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You have a high degree of ownership and move fast.
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You're happy travelling to the Caribbean regularly.
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You have the right to work in the UK.
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You're confident in Excel or Google Sheets. Familiarity with property-management tools helps.
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Additional languages spoken in the Caribbean (e.g. Spanish, Dutch, French) are a plus.
Worth knowing before you apply
This role is based in London, works closely with our COO, and involves regular travel to our Caribbean operations. We're a young company with ambitious plans, and this isn't always a 9-to-5. Our islands run on Caribbean hours and urgent things come in at odd times. In exchange, we're flexible and we trust people: if you've had a heavy week, take the time back and clock off early when it's quiet (just coordinate with your team).
As an early senior hire at HQ, you'll have a real say in how Bocobay operates.
Apply at bocobay.com/careers.
