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.