Orlebar Brown
Head of Technology
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Head of Technology
Role Type
Full Time
Department
Technology
Reporting To
Chief Technology Officer
Location
Fitzrovia, London
Salary
Competitive
Company Profile
Orlebar Brown (Chanel group) launched in March 2007 as a more tailored approach to men’s beach and swim shorts. Based on the traditional pattern of a tailored pair of trousers for men, and with their distinctive side fasteners, they are not just a swim short; they are the original and best shorts you can swim in.
Today, our collections are built into broader lifestyles imagined around Beach, Resort, Coast and Sport. We have multiple product releases, including capsules, new categories and services, over the calendar year to maintain excitement, and interest for our customers.
Since 2007, we have built the brand to achieve our stated purpose which is - to encourage, excite and inspire everyone to ‘Holiday Better’. This is our purpose and why we get out of bed every morning.
The brand has rapidly gained global recognition and is sold through online, more than 30 O.B. stores, and the best retailers and hoteliers in the world. Our customer is truly international, so whether they are in St Barth’s for Christmas with family, Miami for a wild Spring break, a conference in Dubai with a few days off, tacking a boat off the coast of St Tropez, volunteering to replant mangrove plantations in Puerto Rico, walking along a cliff top in Cornwall, or diving off one into a beautiful blue ocean then O.B. should be there to help you do it better.
Our business is built on relationships with those customers, and we strive to maintain our relationship with them, wherever they might be, and provide world class service, when and where they want. It is also built on finding new customers to the brand by welcoming them to join the ever-growing O.B. community.
The Position
We do not sell technology; we create clothing that helps our customers Holiday Better. Technology sits behind that purpose—making the customer experience better, enabling colleagues and helping the business perform at its best.
The Head of Technology will lead a deliberately small, high-performing team and turn business needs into simple, secure and measurable outcomes. The role combines exceptional people leadership, project delivery, business analysis, communication and sound technical judgement.
General Responsibilities
Team Leadership and People Development
- Lead a deliberately small, high-performing Technology team with clear priorities, standards and accountability.
- Build capability through coaching, documentation and knowledge sharing, reducing dependency on individuals and suppliers.
- Create a collaborative culture in which simplicity, ownership and continuous improvement drive excellence.
- Act as a constructive, commercially minded member of the wider leadership team.
Project, Programme and Change Leadership
- Lead complex technology and cross-functional change from definition through implementation, adoption and benefits realisation.
- 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, ensuring delivery to agreed quality, cost and timing.
- Plan testing, communication, training, readiness, handover and post-implementation support from the outset.
Business Analysis and Continuous Improvement
- 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 investment where benefits are unclear.
- Identify opportunities to simplify, standardise, automate or remove unnecessary complexity.
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Communication and Stakeholder Partnership
- 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 wider stakeholders.
- Create clarity where expectations compete, challenge constructively and follow through consistently.
Technology Strategy, Architecture and Technical Governance
- Partner with the Chief Technology Officer to translate strategy into focused roadmaps and priorities.
- Champion a clean, coherent architecture and a philosophy of simplicity: standardise where possible, integrate thoughtfully and customise only where it creates clear value.
- Ensure solutions are secure, scalable, supportable and documented, with clear ownership across their lifecycle.
- Reduce technical debt, duplication and unnecessary complexity so a small team can operate with excellence.
Cybersecurity, Risk and Resilience
- Lead cybersecurity governance, risk management and remediation with the Chief Technology Officer and specialist partners.
- 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.
Business Platforms, Integrations and Automation
- Govern NetSuite, Celigo, OneStock and associated Finance, inventory, fulfilment, operations and reporting processes.
- Prioritise platform improvements by 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.
Power BI, Data and Reporting
- Own the Power BI and reporting roadmap, with transparent prioritisation 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, improving trust through clear definitions and validation.
- Manage internal developers and external reporting partners, reducing duplicated or obsolete reporting.
Innovation, AI and Business Enablement
- Help business leaders identify and evaluate opportunities where technology, automation and AI can 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.
Technology Operations and Service Management
- 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.
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Supplier and Commercial Management
- 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.
Candidate Profile
The successful candidate will be a confident, pragmatic and business-minded technology leader. They will combine exceptional delivery and analysis skills with strong technical judgement, clear communication and a genuine commitment to developing people. We have a flat structure and work as one team, so they will be collaborative, hands-on and comfortable contributing beyond traditional role boundaries to achieve the best outcome for the business.
Essential Experience and Capabilities
- 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.
Desirable Experience
- 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 fulfilment.
- A relevant project, programme or business analysis qualification.
What We Offer
- Being part of a diverse working environment of people who we learn from every day
- The chance to train and develop your skills in a fast-working environment
- Competitive benefits package:
- Physical Wellbeing: Private medical insurance covering pre-existing medical conditions and the ability to add family members, an online GP app with 24/7 appointments, available within 24 hours, and cycle scheme participation for tax-exempt bike and/or accessories purchase.
- Financial Wellbeing: Company pension scheme.
- Lifestyle: Orlebar Brown and CHANEL product discounts and employee-only sales.
- Employee Recognition: Service award incentives, 1-week office closure in August to practice what we preach (paid leave and separate from 25 days annual leave plus UK public holidays).
It’s never just a job at Orlebar Brown. It’s a way of life. We live and breathe our brand values – Tailored, Vibrant and Brave. Our team define who we are and how we get the job done.
At Orlebar Brown, we are focused on creating an inclusive culture that nurtures personal growth, contributing to collective progress. 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.
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