Head of Insurance

JR United Kingdom; Chester; Remote; GBP 60,000 - 90,000; Full time

Job summary

A leading company in the insurance startup space is seeking an experienced underwriter to drive the pricing strategy and manage underwriting policies for their innovative products. This role is fully remote, offering flexibility while still allowing for collaboration with diverse teams. The ideal candidate will have significant experience in underwriting and a strong background in data-driven decision-making.

Benefits

Stock options

Self-care Fridays (no internal meetings)

Qualifications

• 5-10 years of underwriting experience focused on low-severity products.
• Strong pricing and actuarial understanding.
• Experience with performance data in underwriting.

Responsibilities

• Lead underwriting and pricing for high-volume products.
• Develop pricing models based on live data.
• Monitor portfolio data to adapt strategies.

Skills

Underwriting

Pricing models

Risk analysis

Claims management

Data analysis

Communication

Job description

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Our client is a venture-backed startup building a modern MGA from the ground up. They combine automated insurance products with live performance data and risk monitoring tools for enterprise clients. Backed by a reputable reinsurance broker, the company is currently in the process of becoming a Lloyd’s of London Cover holder.

This role will sit within the core insurance team and will be instrumental in shaping risk management, pricing strategy, policy design, and claims oversight for all schemes. The team operates fully remotely, with optional access to office space in central London.

Key Responsibilities

• Own and lead all underwriting and pricing activity for high-volume, low-severity products, including transactional or embedded lines.
• Develop and maintain pricing models driven by live performance data, enabling real-time risk segmentation and pricing adjustments.
• Monitor portfolio-level data to identify trends in claims frequency, severity, or behaviour, and adapt underwriting strategy accordingly.
• Operate independently across risk analysis, pricing strategy, and underwriting decision-making — building tools, models, and processes where needed.
• Define and refine underwriting policy, ensuring alignment with regulatory frameworks and future Lloyd’s Coverholder obligations.
• Liaise directly with enterprise partners on pricing, mid-term adjustments, and ongoing product performance.
• Support claims oversight, ensuring operational delivery aligns with underwriting expectations and customer value.
• Ensure compliance with applicable regulatory obligations across small schemes and delegated authority arrangements.
• Maintain technical documentation for audit readiness and internal transparency.
• Collaborate across product and commercial teams, ensuring underwriting remains aligned with broader business strategy.

Candidate Profile

• 5–10 years of underwriting experience with a focus on high-frequency, low-severity product lines (e.g., affinity, embedded, personal lines, etc.).
• Strong pricing and actuarial understanding, with confidence building or adapting pricing models based on live data.
• Track record of using performance data to make underwriting decisions and refine pricing logic in near real-time.
• Comfortable working autonomously in a fast-paced, startup environment.
• Solid knowledge of MGA operations and regulatory obligations — experience working under delegated authority is highly valued.
• Clear communicator, able to translate technical and pricing decisions to internal teams and external partners.
• Experience in the Lloyd’s market or at an MGA preferred, but not essential.
• ? Stock options
• ? Fully remote (with optional office access in London)
• ? Self-care Fridays (no internal meetings)