At a Glance
- Tasks: Lead the delivery of innovative insurance technology solutions and drive cross-functional collaboration.
- Company: Pikl, a dynamic company revolutionising digital marketplaces with insurance-enabled solutions.
- Benefits: Competitive salary, opportunity for rapid career growth, and a chance to work on impactful projects.
- Other info: Fast-paced environment with opportunities for international expansion and collaboration with top brands.
- Why this job: Join a mission-driven team and make a real difference in the insurance industry.
- 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 in London employer: Pikl
At Pikl, we pride ourselves on being an exceptional employer that fosters a dynamic and collaborative work culture. As the Head of Digital Delivery, you will have the opportunity to lead high-impact projects in a fast-paced scale-up environment, with ample room for professional growth and development. Our commitment to innovation and technology ensures that you will be at the forefront of delivering transformative insurance solutions, all while working alongside a talented team in our vibrant Norwich office.
StudySmarter Expert Advice🤫
We think this is how you could land Head of Digital Delivery in London
✨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 products and services. Understand their tech stack and how they integrate with insurance systems. This will show you're genuinely interested and ready to hit the ground running.
✨Tip Number 3
Practice your delivery skills! Since this role is all about leading teams and managing stakeholders, be ready to showcase your communication style. Use examples from your past experiences to demonstrate how you’ve successfully led cross-functional teams.
✨Tip Number 4
Don’t forget to apply through our website! It’s the best way to ensure your application gets seen. Plus, we love seeing candidates who take that extra step to engage with us directly.
We think you need these skills to ace Head of Digital Delivery in London
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 our needs!
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. Share specific examples of your past successes in leading cross-functional teams and delivering complex projects. We love a good story!
Showcase Your Agile Experience:Since we value Agile delivery, make sure to mention your experience with Agile methodologies. Talk about how you've implemented strong delivery cadences and managed risks in fast-paced environments. We’re all about that hands-on, pragmatic approach!
Apply Through Our Website:We encourage you to apply through our website for a smoother application process. It helps us keep track of your application and ensures you don’t miss out on any important updates. Plus, it’s super easy!
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 teams, and how you’ve managed third-party vendors. Highlight your ability to bring structure and momentum to projects.
✨Prepare for Agile Discussions
Since Agile delivery is key for this role, be prepared to talk about your experience with Agile methodologies. Share specific instances where you implemented strong delivery cadences, like stand-ups and sprint planning, and how you improved delivery predictability.
✨Engage with Stakeholders
Expect questions about stakeholder management. Think of examples where you’ve successfully aligned technical and non-technical audiences. Show that you can communicate effectively with business stakeholders and understand their workflows to ensure smooth project delivery.
