Director of Technology

Employment Type:

Permanent

Location:

Cayman Islands

Industry:

Information Technology

Speciality:

Salary:

USD 120000 - 160000


We are recruiting for a Director of Technology on behalf of a valued organisation seeking to strengthen its technical leadership here in Cayman. In this strategic role, you will take full ownership of the technology function, driving the design, delivery, and evolution of core systems and infrastructure to support continued growth across multiple locations.

Company Information
The company operates within the fast?growing vacation rental and property management industry. With a strong commercial performance and an ambitious expansion plan, the company is known for:
  • A customer?centric approach to service delivery
  • A culture that values innovation, autonomy, and continuous improvement
  • A lean, collaborative team environment where your expertise directly influences product and operational outcomes
  • A growing footprint across the Caribbean, supported by a London?based head office

Responsibilities and Duties
In this role, you will:
  • Own the end?to?end technology stack and set the long?term technical direction
  • Define and implement a unified core data model across bookings, listings, pricing, channels, and operations
  • Architect a robust and scalable relational database and manage migration from existing systems
  • Make key technical decisions, including build?vs?buy assessments and workflow design
  • Establish foundational observability, including logging, alerts, and dashboards
  • Build and oversee resilient ETL pipelines and third?party API integrations
  • Ensure data reliability through strong validation, error handling, and monitoring
  • Partner closely with senior leadership to shape roadmap priorities and influence internal and external product capabilities

Qualifications and Skills
To succeed in this role, you should bring:
  • 5+ years’ experience as a backend, platform, or data engineer
  • Strong relational data modelling expertise (e.g., PostgreSQL, MySQL)
  • Proven experience shipping and maintaining production?grade systems
  • Proficiency in Python, Go, or TypeScript/Node
  • Experience building integrations with third?party APIs and working with cloud infrastructure
  • Sound engineering judgement with the ability to balance quality and pace
  • Comfort taking ownership within a lean, fast?moving environment
Desirable:
  • Experience migrating from no ? code/low ? code tools (Airtable/Zapier/Make/N8N) to custom code + DB
  • Familiarity with Supabase or similar managed Postgres solutions
  • Background in property technology, marketplaces, or operations?heavy, data?driven businesses
  • Interest in mentoring future technical hires and shaping broader engineering strategy

Benefits and Perks
The organisation offers a competitive rewards package, including:
  • The opportunity to shape a high?growth technology function from the ground up
  • Significant autonomy and influence over technical decision?making
  • A collaborative and forward?thinking work culture
  • Exposure to a dynamic and expanding international business
  • Professional development opportunities as the team and technology scale

 
APPLY NOW
Interested in this job?
Save Job

Consultant

CONTACT ME

Similar Jobs


Create as Alert

CREATE

Share this job

SCHEMA MARKUP ( This text will only show on the editor. )
Cayman | BVI | Bermuda | channel islands

Our Jurisdictions

Curious to know more about what it's like living and working in a specific offshore jurisdiction? We've got all the resources in one place to help you in making decisions about such a big move.


Not only do our team have long-standing relationships with top employers in all major offshore jurisdictions, but our team are also headquartered in The Cayman Islands, giving us a unique understanding of what to expect when living and working offshore.

LEARN MORE