Oliver's Travels
Head of Technology
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Head of Technology
Head of Technology / Enterprise Solutions Architect
We're looking for a hands-on Head of Technology / Enterprise Solutions Architect to lead the ongoing evolution, 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 expertise, 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 Travell’s 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, 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.
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Platform & Infrastructure
- Oversee Oliver’s Travel’s website ecosystem, booking platform, APIs, and integration architecture.
- Ensure high availability, resilience, security, and operational performance across all systems.
- 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.
Requirements
Proven Experience
- 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 (SaaS platforms, bespoke applications, and legacy systems).
- Experience managing technology suppliers, implementation partners, and outsourced development teams.
- Comfortable operating within fast-growing 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.
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Personal Attributes
- Strategic thinker with strong commercial awareness and a pragmatic delivery focus.
- Highly effective 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.
What We Offer
- Flexible working – work from anywhere in the world for up to 4 weeks each year.
- £1,000 holiday credit every year to use on one of our gorgeous villas.
- 25 days’ annual leave plus bank holidays, plus one extra day per year of service.
- Birthday off when it falls on a working day.
- Monthly company socials and legendary summer and Christmas parties.
- Free breakfast, snacks, and drinks in the office.
- A friendly, fast-growing team of passionate travellers from all over the world.
- Office dogs – bring yours along!
Application Process
- Apply – Submit your CV
- Screening – A quick intro call to get to know you better
- First interview – Held via Microsoft Teams
- Final interview – In person at our office
Key Details
- Reports to: Founders
- Location: London (Hybrid – 3 days in office)
- Salary: £90,000 - £120,000
We welcome and encourage candidates to apply, even if they don’t meet all the listed requirements.
Oliver’s Travels is an equal-opportunity employer. We do not discriminate based on race, religion, gender, age, sexuality, gender identification, or physical ability.
If you require any adjustments to participate fully in the application process or to perform the duties of this role, please let us know. We are committed to supporting your needs.
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