Head of Engineering Delivery

Job description

About BoyleSports BoyleSports is Ireland’s largest independent bookmaker and a major player in the gambling industry, founded in 1982 by John Boyle. Headquartered in Dundalk, the company operates over 400 retail betting shops across Ireland and the UK alongside a growing digital business. Our focus is on winning in our core UK and Ireland markets, and we are investing heavily in our in-house technology platform to compete and lead on product across our core verticals – sportsbook, gaming and retail – and to become a customer favourite and innovator. BoyleSports Engineering is delivering two major transformation programmes in parallel. On the back end, we are migrating from a monolithic Oracle environment to a modern, event-driven architecture built on microservices (introducing Kafka, decomposing the monolith into transactional and archival components, and migrating to AWS). On the front end, we are unifying twelve fragmented applications into a single, responsive SPA/PWA built on an app-shell and micro-frontend model, migrating from .NET MVC to React, and adopting a headless CMS. Alongside this we are moving from manual to automated testing, and reshaping the organisation around a domain-driven model with full-stack, end-to-end ownership. Our work is organised around clear domain squads – sportsbook, trading, gaming, player account & compliance, payments, bonuses & promotions, retail & omni, and core platform – delivered by engineering teams based mainly in the Republic of Ireland and in our fast-growing technology hub in Serbia, with further colleagues and contractors across the UK, Northern Ireland, Manila and Gibraltar. Coordinating delivery across these domains, programmes and locations is exactly the challenge this role exists to solve. Role Purpose The Head of Engineering Delivery is a new, dedicated leadership role focused squarely on the delivery and coordination of work across our Engineering organisation. Technology at BoyleSports is around 213 people, of which Engineering is 127 – 84 developers and 41 QA – arranged into domain squads. Where our architecture and long-term technical direction are well served, the gap this role fills is the day-to-day orchestration of that Engineering organisation against the product roadmap. You will be the single point of accountability for turning the product roadmap and architectural direction into predictable, well-sequenced delivery. Working hand-in-hand with the Director of Product, our strong Tech Leads, the Solution Architect and the senior architecture leadership, you will plan and coordinate the work of our squads, remove cross-team dependencies and bottlenecks, and ensure that both new features and operational demands – hotfixes, incidents and support escalations – are handled without derailing the roadmap. This is a delivery and people-coordination role, not an architecture role. You will have enough technical depth to earn the respect of senior engineers and to make sound trade-off calls, but your core craft is delivery leadership: planning, agile execution, stakeholder alignment and getting high-quality software shipped. Key Responsibilities Delivery planning and coordination Roadmap to delivery. Translate the product roadmap and architectural direction into realistic, sequenced delivery plans with credible dates that account for proper agile process, build and testing to company standards. Cross-team orchestration. Coordinate the work of our domain squads and strong Tech Leads, owning cross-team dependencies, capacity planning and prioritisation so that the right things are worked on in the right order. Distributed delivery. Coordinate delivery across our Dundalk base and our Serbia technology hub, keeping teams in both locations aligned, well-utilised and productive as the Serbia hub continues to grow. Single source of truth. Drive disciplined use of Azure DevOps so that all work is traceable to registered work items, with clear status visibility from initiative through to deployment, in line with our SDLC. Balancing run and change. Balance feature delivery against operational demand – hotfixes, defects, incidents and support escalations – establishing a clear, fair process for triaging and absorbing unplanned work. Stakeholder alignment Product partnership. Work in lockstep with the Director of Product on roadmap alignment, scope, trade-offs and sequencing, acting as the delivery counterpart to the product function. Support and operations. Partner with support and operations teams to coordinate the response to production issues and hotfixes, ensuring engineering effort is allocated quickly and transparently. Architecture alignment. Collaborate with the senior architecture leadership and the Solution Architect to ensure delivery plans respect the target architecture and the balance between tactical change and long-term strategic goals, minimising technical debt. Commercial and PMO. Engage commercial and operational stakeholders and the PMO on transformation initiatives, reporting clearly on progress, risk and dependencies. Transformation delivery Oversee delivery of the back-end modernisation programme: the move to microservices and event-driven architecture (e.g. Kafka rollout), monolith decomposition into transactional and archival components, AWS cloud migration, and the planned exit from the Oracle database. Oversee delivery of the front-end unification programme: consolidating the twelve fragmented applications into a single app-shell and micro-frontend model, the .NET MVC to React/Material UI migration, the move to SPA/PWA, and adoption of a headless multitenant CMS. Drive the shift from manual to automated, integrated quality assurance and the closing of the engineering capability gaps identified in our strategy (architecture, modern front-end patterns, DevOps automation, cloud-native and quality engineering). Sequence transformation work alongside business-as-usual feature delivery so that modernisation progresses without stalling the roadmap. Ways of working and continuous improvement Agile leadership. Champion and continuously improve agile delivery practices (Scrum, Kanban) and a DevOps culture across squads, breaking down silos and improving flow. Quality built in. Reinforce our Definition of Done, mandatory code review and shift-left, integrated QA so that quality is owned within teams rather than bolted on at the end. CI/CD discipline. Embed our integration and delivery model across squads – trunk-based commit to mainline, self-testing builds, quality gates and SAST, feature toggles, build-binaries-once, and Azure DevOps as the controlled pipeline manager – so releases are fast, repeatable and reliable. Regulated delivery. Ensure delivery respects the regulatory and security obligations of a UK and Ireland gambling operator (e.g. PCI, GDPR and gambling regulations), coordinating compliance-affecting work with the relevant teams. Metrics and reporting. Monitor and report on delivery health – on-time delivery, lead time, throughput, downtime/incident reduction, productivity and technical-debt trends – and use these to drive improvement. People and growth. Support Tech Leads and engineers through clear expectations, coordination and unblocking, contributing to a balanced, domain-centric team model and a culture of continuous learning. Skills and Experience Essential 10+ years in delivery management or engineering leadership, ideally in fast-paced, regulated industries such as gaming, fintech or sports betting. Proven track record coordinating large development organisations (100+ engineers across multiple teams) and breaking down organisational silos. Demonstrable experience delivering large-scale transformation – monolith-to-microservices, event-driven systems (e.g. Kafka), cloud migration (e.g. AWS) and UI modernisation (e.g. React). Deep expertise in agile methodologies (Scrum, Kanban) and DevOps practices, and in tooling such as Azure DevOps for end-to-end work tracking. Excellent stakeholder management and communication skills, with the ability to align engineering with product, support, commercial and operational goals. Experience coordinating distributed delivery across multiple engineering hubs, ideally in a regulated environment with obligations such as PCI and GDPR. Strong enough technical grounding (across stacks such as .NET, Oracle, React, micro-frontends and modern CI/CD) to make credible trade-off decisions – without needing to be the deep technical authority. A track record of balancing tactical delivery against strategic goals, reducing technical debt and delivering measurable improvements in productivity and quality. Desirable Bachelor’s degree in Computer Science, Engineering or a related field. Certifications such as PMP, AWS or Agile/Scrum. Experience coordinating delivery across multiple engineering locations or hubs. Familiarity with domain-driven organisation and team topologies.