Head of Digital Delivery

Head of Digital Delivery | Norwich (Min 2 Days per week in office) | Permanent or Contract

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: WIGs, lead measures, scoreboards, and accountability rhythms)
• 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
• Coach and develop managers and senior individual contributors, strengthening leadership capability across the function
• Partner with the CTO on organisational design, workforce planning, and hiring strategy

Standards, Quality & Technical Excellence

• Establish and uphold best practices across SDLC, code quality, testing, observability, and incident management
• Partner with engineering leadership to ensure systems are scalable, secure, and maintainable
• Drive the adoption of modern development practices (Agile, Dev Ops, 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
• Contribute to budget planning and ensure efficient use of engineering resources and tooling
• Ensure technology delivery meets all regulatory, compliance, and security requirements within the insurance sector
• Embed robust governance and risk management practices across delivery

Executive Partnership

• Act as a trusted deputy to the CTO, representing the technology function in executive discussions, vendor relationships, and board-level updates
• Provide clear, data-driven visibility of delivery performance, risks, and progress

• Significant experience in technology delivery roles, including leadership of both product and engineering teams
• Proven ability to lead and scale high-performing teams (typically 10–25 people) in fast-paced environments
• Strong track record of owning and delivering technology roadmaps, release cycles, and cross-team initiatives
• Experience working within the insurance sector (carrier, MGA, broker, or insurtech), with understanding of core systems and processes
• Hands-on experience implementing modern SDLC practices (Agile, Dev Ops, CI/CD) and product management frameworks
• Demonstrated experience integrating AI tools (e.g. Copilot, Cursor, Claude Code) to enhance development productivity and quality
• Strong leadership skills, with experience managing managers and senior individual contributors
• Ability to operate as a trusted #2, executing autonomously while maintaining alignment with senior leadership
• Exce…