Job Summary

The Founding Engineer will be responsible for Bocobay's technology. 

Bocobay is a rapidly-growing company in the dynamic vacation rental management space. The company is self-funded and profitable, with annual gross reservation revenue in the eight figures. All operations are in the Caribbean, but this role is in the London head office. We have proven the model in two Caribbean islands, and are expanding to the rest of the Caribbean.

We provide end-to-end management services for vacation rental owners, handling everything from listing creation and guest communication to cleaning and maintenance. We are experiencing rapid growth and are looking for a driven and experienced Marketing Director to join our team in London and play a key role in our continued success. We pride ourselves on our customer-centric approach, innovative technology, and strong team culture.

At Bocobay you will:

• Owning the end-to-end stack, setting the technical direction from core data models to integrations and downstream systems
• Defining and implementing our core data model as the single source of truth across bookings, listings, pricing, channels, and operations
• Designing a robust, scalable relational database and leading safe migration from our current Airtable-based setup
• Making critical technical judgments (eg build vs buy or low-code vs custom), as you build future-proof pipelines that support continuous evolution without disrupting the business
• Establishing foundational observability (including logging, alerts, and dashboards) to ensure data reliability and fast issue detection
• Building and overseeing resilient ETL pipelines for third-party APIs, with strong validation, error handling, and monitoring as first-class concerns
• Partnering with the founder to shape workflows and requirements, challenge assumptions, and directly influence the direction of our internal platform and customer-facing products

What we look for:

• Comfortable taking responsibility within lean, smart teams to support continued rapid growth as the main technical owner (we're currently at $35m gross revenue, doubling each year since inception)
• Worked 4-6 years plus as a backend/platform/data engineer
• Have strong relational data modelling skills (using Postgres/MySQL etc) with experience designing schemas and working in messy, real‑world data environments
• Competent at shipping and maintaining production systems (not just prototypes), using judgement to balance doing it properly with this needs to work next week
• Proficient in Python, Go, or TypeScript/Node with experience building production‑grade integrations to third‑party APIs and working with cloud infrastructure (eg serverless functions, managed DBs, scheduled jobs)

Desirable

• Experience migrating from no‑code/low‑code tools (Airtable/Zapier/Make/N8N) to custom code + DB
• Experience with Supabase or similar managed Postgres platforms
• Background in property tech, marketplaces, or other operations‑heavy, data‑rich businesses
• Interest in shaping the broader technical direction and eventually mentoring future hires

What we offer:

• Salary: Competitive
• Option scheme: Inclusion in a significant option scheme
• Benefits: Annual team trip to the Caribbean (potentially more, as required) , Work from anywhere for 2 weeks

Application process:

• 15 min screening call
• 30 min interview with senior team member
• 1 hour case study interview
• 30 min screening call with technical company shareholder
• Lunch with the rest of the London team
• Official Offer