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About the Role
The Head of Technology will lead a high-performing team to transform business needs into simple, secure, and measurable outcomes. This role requires exceptional people leadership, project delivery, business analysis, communication, and technical judgment to support the company's purpose of helping customers 'Holiday Better'.
Responsibilities
- Lead a high-performing Technology team with clear priorities, standards, and accountability.
- Build team capability through coaching, documentation, and knowledge sharing.
- Foster a collaborative culture driven by simplicity, ownership, and continuous improvement.
- Lead complex technology and cross-functional change initiatives from definition through to benefits realization.
- Translate strategy into clear roadmaps and delivery plans with defined outcomes, scope, ownership, resources, milestones, and dependencies.
- Control budgets, risks, issues, decisions, and changes through proportionate governance and transparent reporting.
- Coordinate business teams, specialists, and partners to ensure delivery to agreed quality, cost, and timing.
- Plan testing, communication, training, readiness, handover, and post-implementation support.
- Lead discovery, workshops, and process reviews to understand objectives, user needs, constraints, and root causes.
- Translate needs into clear requirements, priorities, process maps, user stories, acceptance criteria, and delivery plans.
- Use structured analysis and options appraisal to support decisions and challenge investments with unclear benefits.
- Identify opportunities to simplify, standardize, automate, or remove unnecessary complexity.
- Build trusted partnerships across the business and translate complex technology topics into clear choices and decisions.
- Communicate priorities, progress, risks, and decisions concisely to senior leaders and stakeholders.
- Create clarity where expectations compete, challenge constructively, and follow through consistently.
- Partner with the Chief Technology Officer to translate strategy into focused roadmaps and priorities.
- Champion a clean, coherent architecture and a philosophy of simplicity.
- Ensure solutions are secure, scalable, supportable, and documented with clear ownership.
- Reduce technical debt, duplication, and unnecessary complexity.
- Lead cybersecurity governance, risk management, and remediation.
- Embed security, privacy, and resilience into projects, suppliers, system changes, and operating practices.
- Maintain clear ownership and escalation of risks, vulnerabilities, incidents, and improvement actions.
- Lead significant incident response and oversee business continuity, disaster recovery, and resilience testing.
- Govern NetSuite, Celigo, OneStock, and associated Finance, inventory, fulfillment, operations, and reporting processes.
- Prioritize platform improvements based on customer and business value, risk, and strategic alignment.
- Ensure integrations, APIs, and automations are owned, monitored, documented, tested, and supported.
- Maintain sufficient NetSuite, Celigo, and OneStock expertise to challenge designs, assess impact, and hold partners accountable.
- Own the Power BI and reporting roadmap, with transparent prioritization of dashboards and enhancements.
- Translate reporting needs into clear specifications and oversee development, testing, release, adoption, and support.
- Establish governance for data, reports, access, ownership, and change control.
- Manage internal developers and external reporting partners.
- Help business leaders identify and evaluate opportunities for technology, automation, and AI to create measurable value.
- Support business-owned pilots while leading the secure technology delivery, rollout, adoption, and scaling of approved initiatives.
- Drive adoption of Microsoft Copilot and other approved AI capabilities through practical governance, communication, and coaching.
- Define success measures with business owners and turn successful pilots into sustainable capabilities.
- Ensure reliable, well-managed technology services across Head Office, stores, ecommerce, and operations.
- Set service standards, ownership, support models, and escalation routes, using performance and root-cause insight to drive improvement.
- Lead critical incident response and coordinate readiness for launches, peak trading, and major business events.
- Manage suppliers and delivery partners against clear outcomes, service expectations, cost, and performance measures.
- Ensure supplier work is documented, knowledge is transferred, and internal capability is strengthened.
- Manage the Technology budget, forecasts, and investment pipeline, ensuring accurate reporting, clear ownership, and disciplined control of spend.
- Build robust business cases and track costs, benefits, and outcomes to ensure Technology investment delivers measurable value.
Requirements
- Exceptional project and programme management, with a record of delivering complex cross-functional change through adoption.
- Exceptional business analysis, requirements gathering, facilitation, and process improvement.
- Outstanding communication, stakeholder management, and influencing skills.
- Strong people leadership, with evidence of building accountable, high-performing teams.
- Strong technical breadth across enterprise applications, integrations, data, cloud, cybersecurity, and operations.
- Working knowledge of NetSuite, Celigo, and OneStock, plus experience governing Power BI and reporting development.
- Experience managing cybersecurity, suppliers, and business-critical platforms in a retail, ecommerce, consumer, luxury, or omnichannel environment.
- Experience with Microsoft Copilot, responsible AI governance, or business-led innovation.
- Exposure to Microsoft Fabric, Shopify, Ometria, Centric, or comparable platforms.
- ERP or Finance transformation experience and an understanding of stores, POS, payments, inventory, and fulfillment.
- A relevant project, programme, or business analysis qualification.
Skills
- People leadership
- Project delivery
- Business analysis
- Communication
- Technical judgment
- Cybersecurity governance
- Risk management
- Business continuity
- Disaster recovery
- NetSuite
- Celigo
- OneStock
- Power BI
- Reporting development
- Microsoft Copilot
- AI governance
- Automation
- Cloud
- Integrations
- Data management
- Stakeholder management
- Process improvement
Location
- Fitzrovia, London
Work Type
- Full Time
Experience Level
- Head of Technology
Education Level
- Relevant project, programme or business analysis qualification
Salary/Compensations
- Competitive
Benefits
- Private medical insurance covering pre-existing medical conditions
- Ability to add family members to medical insurance
- Online GP app with 24/7 appointments, available within 24 hours
- Cycle scheme participation for tax-exempt bike and/or accessories purchase
- Company pension scheme
- Orlebar Brown and CHANEL product discounts
- Employee-only sales
- Service award incentives
- 1-week office closure in August (paid leave)
- 25 days annual leave plus UK public holidays
About the Company
- Orlebar Brown (Chanel group) launched in March 2007, offering a tailored approach to men’s beach and swim shorts.
- The brand has expanded into broader lifestyle collections for Beach, Resort, Coast, and Sport.
- The company's purpose is to encourage, excite, and inspire everyone to ‘Holiday Better’.
- Orlebar Brown has gained global recognition and is sold through online channels, over 30 stores, and select retailers and hoteliers.
- The business is built on relationships with international customers and aims to provide world-class service.
- The company focuses on creating an inclusive culture that nurtures personal growth and collective progress.
Equal Opportunity
- We believe the uniqueness of each individual increases the diversity, complementarity and effectiveness of our teams. We strongly encourage your application, as we value the perspective, experience and potential you could bring to Orlebar Brown.