At a Glance
- Tasks: Lead the delivery of innovative insurance technology projects and drive cross-functional collaboration.
- Company: Join Pikl, a dynamic company revolutionising digital marketplaces in the insurance sector.
- Benefits: Competitive salary, flexible working, and the chance to make a real impact.
- Other info: Fast-paced environment with a focus on innovation and international expansion.
- Why this job: Be at the forefront of technology in a high-impact role with rapid growth opportunities.
- Qualifications: Proven experience in delivering complex insurance systems and leading diverse teams.
The predicted salary is between 80000 - 100000 £ per year.
We’re looking for an experienced Head of Digital Delivery to support a critical phase of delivery at Pikl. Working closely with the CTO, this role is focused on driving the implementation and evolution of policy administration systems and other insurance products, ensuring strong execution across product, engineering, and business teams. Leading a cross-functional product and engineering function, you’ll play a key role in bringing structure, momentum, and delivery confidence to a high-impact area of our technology roadmap.
Key Requirements:
- Lead the end-to-end delivery of policy administration system initiatives
- Drive execution across engineering, product, and third-party vendors
- Establish clear delivery plans, milestones, and dependencies
- Proactively manage risks, blockers, and escalations to maintain delivery momentum
- Work closely with business stakeholders (underwriting, claims, operations) to ensure alignment with real-world workflows
- Coordinate integrations across core insurance systems (policy admin, billing, claims, rating engines, etc.)
- Implement strong delivery cadence (stand-ups, sprint planning, reporting, governance)
- Improve delivery predictability, transparency, and stakeholder confidence
- Support vendor management where external platforms or system providers are involved
What we’re looking for:
- Proven experience delivering policy administration systems (Guidewire, Duck Creek, CDL, Open GI, or similar) or similar complex insurance systems.
- Significant experience in technology delivery roles, including leadership of both product and engineering teams
- Experience working across core insurance systems and workflows (underwriting, claims, billing)
- Track record of delivering complex, cross-functional technology initiatives
- Confident managing both internal teams and third-party vendors/platform providers
- Strong understanding of Agile delivery, with the ability to bring structure to evolving environments
- Excellent stakeholder management skills, particularly across technical and non-technical audiences
- Hands-on, pragmatic approach—comfortable operating in a fast-paced, scale-up environment
- Exposure to system migrations, integrations, or platform replacements
- Familiarity with modern engineering practices (CI/CD, DevOps)
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.
Why join us?
You’ll be working on business-critical insurance platforms at a company where technology is central to growth. This is a high-impact role with visibility across the business and the opportunity to drive meaningful delivery outcomes quickly. Interested? We’re looking to move quickly and prioritising candidates who can start immediately or at short notice.
Head of Digital Delivery employer: Pikl
Pikl is an exceptional employer that places technology at the heart of its mission to revolutionise digital marketplaces, particularly in the insurance sector. With a dynamic work culture that fosters collaboration and innovation, employees are empowered to lead impactful projects while benefiting from professional growth opportunities in a fast-paced scale-up environment. Located in vibrant Norwich and London, Pikl offers a unique chance to contribute to high-stakes initiatives alongside industry leaders, ensuring that your work directly influences the future of insurance-enabled solutions.
StudySmarter Expert Advice🤫
We think this is how you could land Head of Digital Delivery
✨Tip Number 1
Network like a pro! Reach out to your connections in the industry, especially those who might know someone at Pikl. A friendly chat can sometimes lead to a referral, which is golden when it comes to landing that interview.
✨Tip Number 2
Prepare for the interview by diving deep into Pikl's mission and products. Show us you understand how policy administration systems work and how they fit into the bigger picture of insurance. This will help you stand out as a candidate who’s genuinely interested.
✨Tip Number 3
Practice your delivery skills! You’ll need to demonstrate your experience in leading cross-functional teams and managing stakeholders. Use real examples from your past roles to illustrate how you’ve tackled challenges and driven successful outcomes.
✨Tip Number 4
Don’t forget to apply through our website! It’s the best way to ensure your application gets seen by the right people. Plus, it shows us you’re serious about joining the team at Pikl.
We think you need these skills to ace Head of Digital Delivery
Some tips for your application 🫡
Tailor Your CV:Make sure your CV speaks directly to the role of Head of Digital Delivery. Highlight your experience with policy administration systems and any relevant technology delivery roles. We want to see how your background aligns with what we’re looking for!
Craft a Compelling Cover Letter:Your cover letter is your chance to shine! Use it to explain why you’re the perfect fit for Pikl. Mention specific projects where you’ve led cross-functional teams and delivered complex initiatives. Let us know how you can bring structure and momentum to our tech roadmap.
Showcase Your Stakeholder Management Skills:In your application, don’t forget to highlight your experience in managing both technical and non-technical stakeholders. We’re keen to see examples of how you’ve successfully navigated these relationships to drive delivery outcomes.
Apply Through Our Website:We encourage you to apply through our website for a smoother process. It’s the best way for us to receive your application and get you into our system quickly. Plus, it shows you’re serious about joining our team at Pikl!
How to prepare for a job interview at Pikl
✨Know Your Stuff
Make sure you’re well-versed in policy administration systems like Guidewire or Duck Creek. Brush up on your knowledge of core insurance workflows, as you'll need to demonstrate your understanding of how these systems integrate with underwriting, claims, and billing.
✨Showcase Your Leadership Skills
Be ready to discuss your experience leading cross-functional teams. Prepare examples of how you've driven execution across product and engineering functions, and how you’ve managed both internal teams and third-party vendors to achieve delivery goals.
✨Prepare for Agile Discussions
Since this role requires a strong understanding of Agile delivery, be prepared to talk about your experience with Agile methodologies. Share specific instances where you’ve implemented delivery cadences like stand-ups and sprint planning to improve project outcomes.
✨Engage with Stakeholders
Highlight your stakeholder management skills by preparing examples of how you've aligned technical and non-technical audiences. Discuss how you’ve maintained transparency and built confidence among stakeholders during complex technology initiatives.
