Role Overview
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.
Key Responsibilities
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
Required Experience
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
