Head of Delivery - Digital in Norfolk, Norwich

We’re seeking a Head of Digital Delivery to join Pikl at a pivotal stage of growth. Reporting to the CTO, the Head of Digital Delivery is responsible for translating strategy into execution, ensuring that our product and engineering teams consistently deliver high-quality outcomes at pace. While the CTO defines direction, architecture, and long-term vision, you will own the operational engine that brings that vision to life. You will lead a high-performing product and engineering function, driving clarity, accountability, and predictable delivery across the roadmap. This role combines delivery excellence, team leadership, and commercial alignment. You will play a key part in scaling our technology capability, embedding modern delivery practices, and ensuring that technology is a true driver of business performance.

Delivery Leadership & Execution

• Own end-to-end delivery of the technology roadmap, turning strategic priorities into clear plans, milestones, and measurable outcomes.
• Establish and run a high-performance delivery operating cadence (including 4DX principles: Ensure predictable, high-quality delivery with continuous improvement in speed, reliability, and output).
• Act as the primary escalation point for delivery risks, dependencies, and cross-functional trade-offs.
• Lead, develop, and scale the product and engineering organisation, including product managers, engineering managers, and delivery leads.
• Build a high-performance culture focused on ownership, accountability, collaboration, and continuous improvement.

Standards, Quality & Technical Excellence

• Establish and uphold best practices across SDLC, code quality, testing, observability, and incident management.
• Drive the adoption of modern development practices (Agile, DevOps, CI/CD) and tooling.
• Champion the effective use of AI-assisted development tools to improve productivity, quality, and team output.

Performance & Commercial Alignment

• Define and track key delivery and engineering metrics, including throughput, velocity, defect rates, lead time, and team health.
• Ensure delivery priorities are tightly aligned to business and commercial outcomes.
• Work closely with stakeholders across underwriting, claims, distribution, operations, and finance to balance speed, cost, and value.

Governance, Risk & Compliance

• Ensure technology delivery meets all regulatory, compliance, and security requirements within the insurance sector.
• Embed robust governance and risk management practices across delivery.
• Provide clear, data-driven visibility of delivery performance, risks, and progress.

Hands-on experience implementing modern SDLC practices (Agile, DevOps, CI/CD) and product management frameworks. Demonstrated experience integrating AI tools (e.g. Copilot, Cursor, Claude Code) to enhance development productivity and quality. Excellent stakeholder management skills, with the ability to balance technical, commercial, and operational priorities. Experience working in regulated environments and ensuring compliance within technology delivery.

We're moving quickly and are particularly keen to speak to candidates that can join immediately or on short notice - either on a contract or permanent basis. Pikl is on a mission to enable the growth of digital marketplaces, starting with vacation rentals. We design and deliver insurance-enabled solutions that help platforms, property managers and owners unlock new revenue and deliver better customer experiences. Founded in 2016, we began by protecting individual hosts and homeowners with specialist holiday-let cover. With offices in Norwich and London, and plans for international expansion, we work with some of the most recognised brands in travel as well as major insurance aggregators.

At Pikl, our values are the foundation on which our success is built. We put people first, building relationships rooted in empathy and trust. We unlock growth opportunities for our customers and each other yet make it our personal responsibility to own actions and see them through. Flexible working conditions, access to an incredible in-person working space ~ Annual holiday entitlement of 28 days plus bank holidays ~ Training and development opportunities ~ Social events.