Head of Underwriting

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.

About the Role

The Head of Underwriting is a senior leadership position responsible for shaping, governing, and driving Pikl’s underwriting strategy across all product lines. This role will lead the development of underwriting philosophy, technical standards, governance frameworks and pricing oversight, ensuring Pikl delivers sustainable, profitable growth across its portfolio.

You will work closely with internal teams including Business Solutions, Digital Studio & Commercial as well as with insurer capacity partners to build a market‑leading underwriting function. You’ll own delegated authority frameworks, oversee the creation and approval of new insurance products, ensure compliance, and drive continuous improvement in underwriting processes and performance.

This role is pivotal in enabling Pikl’s next phase of scale and expansion.

Key Responsibilities

Strategic Leadership & Underwriting Governance

• Develop and own Pikl’s underwriting strategy, philosophy and appetite across all product lines.
• Establish and maintain underwriting governance frameworks, controls and standards.
• Lead oversight of delegated underwriting authorities, ensuring compliance with capacity provider terms, regulatory requirements and internal policies.
• Build and mentor a high performing underwriting team, promoting technical excellence and continuous development.

Product & Proposition Development

• Oversee the creation, refinement and sign‑off of policy wordings, endorsements and underwriting guidelines.
• Partner with the Head of Propositions and wider product teams to shape and approve new product designs, ensuring alignment with underwriting appetite and capacity arrangements.
• Provide underwriting leadership in the operationalisation of new and bespoke products, ensuring seamless integration with systems and workflows.

Capacity & Partner Management

• Act as the primary technical underwriting contact for insurer partners, maintaining strong relationships and ensuring continued support and capacity allocation.
• Lead reporting, portfolio reviews, performance insights and renewal negotiations with existing and prospective capacity providers.
• Support partner product implementations, underwriting due diligence and technical validation.
• Oversee pricing governance and portfolio monitoring, working with pricing and data teams to ensure performance meets loss ratio and profitability targets.
• Use emerging trends, data insights and market intelligence to shape underwriting strategy and inform product development.
• Ensure the business remains compliant with regulatory changes impacting underwriting and product design.

Stakeholder Collaboration

• Provide expert underwriting insight to support commercial initiatives, sales conversations, and partner onboarding.
• Work closely with operations and technology teams to drive efficiency, improve underwriting workflows, and identify opportunities for automation or optimisation.
• Review and approve marketing collateral and partner customer journeys from an underwriting and regulatory perspective.

About You

• Proven leadership experience in a senior underwriting role, ideally as a Head of Underwriting, or similar.
• Deep technical knowledge across liability and/or property products, with experience in bespoke or niche insurance solutions.
• Strong experience managing delegated authorities, capacity relationships and regulatory compliance.
• Track record of developing underwriting strategy, guidelines and governance frameworks.
• Strong analytical, commercial and decision‑making skills, with the ability to balance innovation and risk management.
• Excellent communication and stakeholder management skills, able to influence at senior levels both internally and externally.
• Confident leading cross‑functional initiatives and partnering with product, operations, commercial and technology teams.

Desirable but not essential

• Professional insurance qualifications (e.g., ACII or equivalent).
• Experience within the sharing economy, platform economy, or digital marketplace sectors.
• Experience working in an MGA or start‑up/scale‑up environment.

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

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