Head of Technology

We’re looking for a Head of Technology to lead the strategy, architecture, stability and performance of Oliver’s Travels’ digital platforms and technology estate.

This is a senior leadership role responsible for defining the long-term technology strategy and enterprise architecture that underpins the business, whilst ensuring the day-to-day delivery, reliability and continuous improvement of our technology platforms.

The successful candidate will combine strong technical leadership with enterprise solution architecture judgement, working across business and technology teams to design scalable, integrated solutions that support business growth, operational efficiency and future transformation., Technology Strategy & Architecture

• Own the overall technology strategy, architecture and technical direction across Oliver’s Travels’ technology estate
• Design end-to-end enterprise solutions spanning customer-facing platforms, operational systems and third-party services
• Lead technical decision-making, technology roadmaps and engineering standards
• Ensure technology decisions align with long-term commercial objectives
• Define integration strategies across CRM, booking systems, finance platforms, payment providers and external partners
• Evaluate new technologies and SaaS platforms to ensure alignment with strategic architecture
• Identify opportunities to modernise legacy systems, reduce technical debt and simplify the technology landscape

Engineering & Delivery

• Manage internal developers and third-party agencies and freelancers
• Introduce and improve development processes, QA, deployment and release management
• Ensure technology initiatives are delivered on time, within budget and to a high standard
• Promote DevOps, CI/CD and automation best practices across engineering teams

Platform & Infrastructure

• Oversee Oliver’s Travels’ website ecosystem, booking platform, APIs and integration architecture
• Ensure high availability, resilience, security and operational performance across all systems
• Lead platform scalability initiatives and drive improvements in site performance and customer experience
• Oversee cloud infrastructure strategy and technology lifecycle management

Commercial & Stakeholder Management

• Partner with founders and senior leadership to shape technology strategy and investment priorities
• Manage technology budgets, suppliers and strategic technology partners
• Present architecture proposals and technical recommendations to senior stakeholders in a clear, commercial manner

• Proven experience in a senior technology leadership role (Head of Technology, Head of Engineering, Enterprise Architect, Solutions Architect or similar)
• Significant experience designing enterprise-scale solution architectures
• Strong understanding of enterprise integration patterns, APIs, middleware and distributed systems
• Experience managing mixed technology ecosystems including SaaS platforms, bespoke applications and legacy systems
• Experience managing technology suppliers, implementation partners and outsourced development teams
• Comfortable operating within fast-moving SMEs or scale-up businesses

Desirable Experience

• Experience with booking, travel, hospitality or e-commerce platforms
• Cloud architecture (AWS, Azure or GCP) and DevOps practices
• Experience modernising legacy platforms through incremental transformation

Personal Attributes

• Strategic thinker with strong commercial awareness and pragmatic delivery focus
• Strong communicator capable of engaging both technical and non-technical stakeholders
• Highly organised with strong planning and prioritisation skills
• Collaborative, inquisitive and passionate about continuous improvement