Head of Technology & AI

Reports to: Chief Executive Officer Location: Hybrid - London (Head Office), Farthingstone (Hotel), WFH Contract: Permanent, full-time About Fifty Five Hospitality Fifty Five Hospitality is creating a new brand of ultra-luxury hotels and resorts rooted in nature and wellness within easy reach of global gateway cities. Our first hotel, Farthingstone, is a new-build ultra-luxury countryside hotel in Northamptonshire, less than two hours north of London, in an outstanding natural environment with an exceptional wellness offering. Future hotels will follow in prime international locations. We are a small, private equity-backed team of experienced hotel executives, a two-Michelin-starred chef, and specialists from corporate, interior design and global creative backgrounds. As owner, developer, brand and operator, we are building a hospitality company from the ground up, so every hire is fundamental in shaping how we build and how we operate. This is a rare opportunity to design a technology function, and an entire hotel technology estate, from a blank page rather than inherit legacy systems, data and process. Role Purpose The Head of Technology & AI is a newly created role, reporting directly to the CEO and working closely with the wider executive team. Whilst the role sits at head office rather than at asset level, reflecting that the expertise will be deployed across the portfolio as it grows, its initial focus is Farthingstone, our first hotel. The mandate there covers three things: the design and delivery of the physical technology infrastructure on site; the selection, implementation and ownership of the entire software stack across head office and hotel; and company-wide AI strategy. This is a senior role, but a deliberately hands-on one. There is no technology team beneath it. The successful candidate owns both the strategy and its execution, working through consultants, specialist contractors and managed service providers, leading their own function, and coordinating closely with every other part of the business. The person in this role will set the standard for what the technology estate of an ultra-luxury hotel should look like, and that standard will carry into every asset that follows. Key Responsibilities Pre-Opening: Systems & Software Stack - Working with our hotel technology consultant, lead the selection and implementation of the full software stack: PMS, POS, booking and channel management, CRM, spa and activity scheduling, revenue management, restaurant reservations, housekeeping and maintenance, procurement, finance, and HR and payroll. - Own integration end to end, so the stack operates as one ecosystem with a single source of truth for guest and financial data. - Translate the operating requirements of the operations, F&B, spa, commercial and finance leads into system design and configuration. - Own the guest-facing digital estate alongside marketing: website, booking flow, in-room and guest-app technology, and pre-arrival and post-stay communication. - Set the architecture principles the business will work to: system integration, data flow, a single source of truth for guest and financial data, and the standards every future property will inherit. Pre-Opening: Strategy, Infrastructure & Governance - Define and own the group technology strategy, roadmap and budget, designed from the outset to scale across future assets. - Lead the physical technology strategy at Farthingstone, front and back of house: fibre, structured cabling, networking and Wi-Fi, telephony, AV, guest room technology, CCTV, access control and locking, EPOS hardware, and staff devices. - Define BMS requirements with the operational team, and the integrations that deliver real-time monitoring, automated adjustment, and resilience across the site. - Own the technology elements of the project programme with the design team, contractors and specialist subcontractors, from specification through commissioning and handover, escalating cost, programme and quality risk to the CEO and VP of Development. - Lead build-versus-buy and vendor selection: technical and commercial evaluation, contract and service-level negotiation, and avoiding lock-in that would constrain later assets. - Establish IT and data governance and cyber security from first principles: data ownership and retention, access control, UK GDPR, PCI DSS, identity and access management, endpoint and network security, incident response, and business continuity. Hotel Opening - Plan and lead the technology programme through to go-live: data set-up, testing, commissioning and soak testing. - Deliver system training for an operating team recruited from scratch, and ensure the estate is ready to trade ahead of the soft-opening programme. - Run technology snagging and defects with contractors through handover and the defects liability period. - Stand up the support model: service desk, response standards, on-site versus outsourced support, asset register, and lifecycle planning. Ongoing Operations - Serve as the senior point of escalation for system-wide technology issues, distinguishing routine maintenance matters from infrastructure-level problems that require strategic oversight. - Own the operating technology cost base: licensing, subscriptions, support renewals, and replacement planning. - Maintain and test security, business continuity and disaster recovery, and own the technology inputs to insurance, audit and investor reporting. AI Strategy & Adoption - all phases - Own company-wide AI strategy, identifying where AI creates commercial or operational advantage across finance, operations, marketing and guest experience, and working with those departments to deploy it. - Translate opportunities into commercial business cases, then deliver them, within practical guardrails for data privacy, accuracy, guest-facing appropriateness and acceptable use. Leadership & Stakeholder Management - all phases - Act as a senior technology and AI advisor to the executive team, translating complex options into clear commercial recommendations for a non-technical audience, and contribute to executive and investor reporting on technology progress, spend and risk. - Lead the technology function and own its budget, priorities and standards. There is no immediate expectation of team growth; the successful candidate will determine what resource they need as the portfolio scales. - Manage external IT advisors and managed service providers, ensuring their input is well-directed and complementary to in-house strategy rather than a substitute for it. Candidate Profile - Exceptional technical depth, acquired in a technology-first environment. We would rather appoint an outstanding technologist with no hospitality background than a hospitality IT specialist who is average at technology. - Track record of building technology infrastructure from scratch - this is a builder's role, not a management role over an existing estate. - Strong infrastructure and networking fundamentals alongside applications, integration and data experience; equally comfortable interrogating a specification, challenging a contractor, or configuring a system personally. - Practical experience overseeing AV/IT installation in a construction or fit-out context, in any sector. - Personal ownership of security, data governance and compliance rather than delegation of it, and genuine deployed experience with AI tools in a business context. - Commercially minded on build-versus-buy, with real experience of vendor selection, contract and service-level negotiation, and budget ownership. - Comfortable as a hands-on sole technology specialist in a small, fast-moving, PE-backed business, and able to win the confidence of non-technical operators; this role is judged on adoption, not architecture. - Hotel or resort experience is preferred but not required. Willingness to spend significant time on site at Farthingstone through the delivery and pre-opening phases is. What We Offer - Competitive salary with discretionary annual bonus. - Enhanced pension scheme. - Salary sacrifice schemes (EV, cycle-to-work) available after probation. - Private medical and dental insurance. - 33 days’ annual leave (including bank holidays).