At a Glance
- Tasks: Lead and scale high-performing product and engineering teams to deliver innovative technology solutions.
- Company: Join Pikl, a dynamic company transforming digital marketplaces with cutting-edge insurance solutions.
- Benefits: Enjoy flexible working, 28 days holiday, and access to wellbeing services.
- Other info: Be part of a mission-driven team with opportunities for growth and development.
- Why this job: Make a real impact in a fast-paced environment while driving technology excellence.
- Qualifications: Proven leadership in tech delivery and experience with Agile and DevOps practices.
The predicted salary is between 80000 - 100000 £ per year.
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.
Head of Digital Delivery in Norwich employer: Pikl
Pikl is an exceptional employer that prioritises employee growth and well-being, offering flexible working conditions and a vibrant office environment in Norwich. With a strong focus on team collaboration and continuous improvement, employees benefit from comprehensive training opportunities and support from an award-winning leadership team, making it an ideal place for those looking to make a meaningful impact in the digital marketplace sector.
StudySmarter Expert Advice🤫
We think this is how you could land Head of Digital Delivery in Norwich
✨Tip Number 1
Network like a pro! Reach out to your connections in the industry, attend relevant events, and don’t be shy about letting people know you’re on the lookout for opportunities. You never know who might have the inside scoop on a role that’s perfect for you.
✨Tip Number 2
Prepare for interviews by researching the company and its culture. Understand their products and services, especially how they align with your skills in digital delivery. This will help you tailor your responses and show them you’re genuinely interested in being part of their team.
✨Tip Number 3
Practice your pitch! Be ready to explain how your experience aligns with the role of Head of Digital Delivery. Highlight your leadership skills and how you’ve successfully driven teams to deliver high-quality outcomes in fast-paced environments.
✨Tip Number 4
Don’t forget to apply through our website! It’s the best way to ensure your application gets noticed. Plus, we love seeing candidates who are proactive and engaged with our brand. Let’s get you on board!
We think you need these skills to ace Head of Digital Delivery in Norwich
Some tips for your application 🫡
Tailor Your Application:Make sure to customise your CV and cover letter for the Head of Digital Delivery role. Highlight your experience in technology delivery and leadership, and show how you can translate strategy into execution. We want to see how your skills align with our mission at Pikl!
Showcase Your Achievements:Don’t just list your responsibilities; share your successes! Use specific examples that demonstrate your ability to lead high-performing teams and deliver technology roadmaps. We love seeing quantifiable results that reflect your impact in previous roles.
Be Authentic:Let your personality shine through in your application. We value people who are genuine and passionate about what they do. Share your story and why you’re excited about the opportunity to work with us at Pikl!
Apply Through Our Website:We encourage you to apply directly through our website. It’s the best way for us to receive your application and ensures you don’t miss any important updates. Plus, it shows you’re keen on joining our team!
How to prepare for a job interview at Pikl
✨Know the Tech Roadmap Inside Out
Before your interview, make sure you thoroughly understand the technology roadmap of the company. Familiarise yourself with their current projects and how they align with business goals. This will help you demonstrate your ability to own and deliver on strategic priorities.
✨Showcase Your Leadership Style
Be prepared to discuss your leadership approach and how you've successfully scaled high-performing teams in the past. Share specific examples of how you've built a culture of accountability and collaboration, as this is crucial for the Head of Digital Delivery role.
✨Emphasise Modern Practices
Highlight your hands-on experience with modern SDLC practices like Agile, DevOps, and CI/CD. Discuss how you've implemented these methodologies in previous roles to improve delivery speed and quality, as this aligns with the expectations of the position.
✨Prepare for Stakeholder Management Scenarios
Expect questions about how you've managed stakeholders across various functions. Prepare examples that illustrate your ability to balance technical, commercial, and operational priorities, ensuring that delivery aligns with business outcomes.
