Head of Operations, Bocobay
Reports to COO
£65-75k
+ equity scheme
4+ days a week in office (Victoria, London)
Market-leading proptech platform and operator ($35m annual revenue)
Posted today
Market-leading proptech platform and operator ($35m annual revenue)
21-100 employees
Posted today
£65-75k
+ equity scheme
4+ days a week in office (Victoria, London)
21-100 employees
Company mission
To be the go-to hospitality brand in the Caribbean, through a unique mix of technology and scaled local operations.
Role
Who you are
- You've built and improved operational systems in a fast-growing, multi-site business.
- You're a critical thinker who uses data to verify assumptions, and then moves quickly and decisively on these insights.
- You understand that operations is not always a 9-to-5.
- You are willing to travel regularly to the Caribbean.
Desirable
- You have some prior hospitality experience.
What the job involves
- Own escalations from across the islands: triage them, resolve them, and get them handled at the right level
- Keep our operational data and systems clean and consistent across our tools (CRM, Hostaway, Breezeway, Conduit and others)
- 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
- Work with on-island leaders and our global contractor teams to raise standards and follow-through everywhere we operate
- Dig into why things keep going wrong and fix the cause, not the symptom
- Get each new market operationally ready as it comes online, and mature the ones already running
- Give the COO a clear view of what's happening operationally, and flag risks early
Salary benchmarks
Our take
Online travel platforms like Airbnb have transformed global travel, with COVID accelerating the shift toward private, professionally managed stays. Bocobay is taking this evolution further - disrupting the luxury rental market with a scalable, asset-light model powered by proprietary operating technology.
London-headquartered and growing quietly but rapidly, Bocobay has delivered consistent 2x year-on-year growth across multiple digital travel channels. By focusing from the outset on the pan-Caribbean market, the company is building a category-defining platform that benefits both sides of the market.
Bocobay enables homeowners and developers to unlock significantly higher yields from their properties, while guests enjoy consistently exceptional, design-led stays - without the friction typical of short-term rentals.
Already operating across Aruba, Curaçao, and Jamaica, Bocobay has ambitious internationally expansion plans underway as it continues to professionalise systems, scale its technology, and build out a world-class leadership team.
Kirsty
Company Specialist at Welcome to the Jungle
Insights
60% female employees
Company
Company benefits
- Annual team trip to the Caribbean (potentially more, as required) 😎
- Equity options (EMI share option scheme)
- Work from anywhere for 2 weeks
- 25 days holiday + bank holidays
- Plus everything else you would expect (inspiring Victoria office, new Macbook, WFH Fridays etc)
Company values
- Be the solution: Our job isn't done until the job is done
- Default to action: Do it now; update others after.
- Be resourceful: Turn constraints into solutions.
Company HQ
Victoria, London, UK
Articles
Leadership
Nick Curtis
(Founder)Nick founded Bocobay, which has doubled its revenues every year into the eight figures, after graduating from Oxford mathematics.
Fabian Weiss
(COO)Fabian has worked for over a decade in operations management at Amazon and Nike, after he graduated from Cambridge.
People progressing
Tara started with Bocobay as a field agent, and in the space of two years has been promoted three times. Tara currently leads the on-the-ground operation in Aruba, Caribbean.
Diversity, Equity & Inclusion at Bocobay
Charlotte Moreno (Managing Director, Aruba)
- We’re an equal opportunity employer and believe that diverse perspectives, backgrounds, and experiences are fundamental to building high-performing teams.
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