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.
About the Role
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.
Key Responsibilities
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
Team Leadership & Organisation Scaling
- 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, 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
- Contribute to budget planning and ensure efficient use of engineering resources and tooling
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
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
About You
- 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, DevOps, 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
- 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.
About Pikl
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. That experience now powers our insurance-enabled products, which increase participation, lift conversion and drive revenue across the marketplace value chain: platforms, homeowners and guests.
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.
Our Values
At Pikl, our values are the foundation on which our success is built. They guide how we work together, how we make decisions for customers and colleagues, and what we recognise and reward.
Possibility
We think big and are fearless in turning challenges into opportunities. We stay curious, test ideas and learn quickly.
People
We put people first, building relationships rooted in empathy and trust. We respect, include, and learn from one another. We celebrate progress.
Progress
We unlock growth opportunities for our customers and each other yet make it our personal responsibility to own actions and see them through.
Why work at Pikl
- Flexible working conditions, access to an incredible in-person working space
- Support from an awarding-winning CEO & Founder
- Annual holiday entitlement of 28 days plus bank holidays
- 35 hour working week
- Death in service scheme
- Access to wellbeing services
- Training and development opportunities
- Social events