Senior Commercial Motor Fleet Underwriter

Introduction

At Pen, we don’t just underwrite risk, we unlock possibility. We’re a dynamic underwriting and distribution business backed by the strength of Gallagher and powered by a belief that every challenge has a solution. With entrepreneurial energy, niche expertise, and a bold growth mindset, we’re transforming what it means to be an MGA in today’s insurance landscape. Whether you’re shaping new products, solving complex problems, or collaborating across teams, your ideas and initiative will help deliver smarter solutions for our clients—and move the industry forward. Here, agility meets stability. Creativity meets execution. And your career meets real opportunity. At Pen, we champion innovation, value accountability, and thrive on building something better together. If you’re looking to join a team that’s rewriting the future of underwriting, we’d love to hear from you.

Overview

We're looking for an experienced Senior Commercial Motor Fleet Underwriter to join Pen Underwriting's specialist Hazardous Goods & Environmental team in Leatherhead.

 

This is an opportunity to join one of the market's most recognised names in hazardous transport and environmental risk, underwriting complex commercial motor fleet portfolios for businesses operating across haulage, waste management, recycling, environmental services and specialist transport sectors.

 

Working within a close-knit, high-performing team, you'll manage major broker relationships, handle technically challenging risks and play a key role in delivering profitable growth, while benefiting from genuine career progression opportunities within a growing specialist business.

 

How you'll make an impact

• Manage a portfolio of commercial motor fleet accounts, including some of the business's largest and most complex risks.
• Underwrite both renewal and new business cases, balancing technical underwriting expertise with commercial decision making.
• Assess risk, set terms and pricing, and manage cases ranging from smaller fleets through to significant corporate accounts.
• Build and maintain strong relationships with brokers and occasionally represent the business in face-to-face meetings with brokers and clients.
• Work closely with insurer partners on larger and referred risks.
• Contribute to profitable portfolio growth within a fast-paced and highly competitive market.
• Share technical expertise and support the wider underwriting team where appropriate.

 

 

About you

Essential Experience

• Strong experience in Commercial Motor Fleet Underwriting is essential. This could be gained within Commercial Motor, Fleet, Haulage, Transport or Commercial Vehicle insurance portfolios.
• Experience underwriting commercial vehicle fleets rather than personal motor insurance.
• Confident handling larger and more complex risks, ideally with exposure to premiums of up to £500,000 or more.
• Experience building and maintaining relationships with brokers and other external stakeholders.
• Comfortable operating within a fast-paced, commercially focused underwriting environment.
• Strong technical underwriting and risk assessment skills.

Desirable Experience

• Experience underwriting haulage, tanker, transport, logistics or specialist fleet risks.
• Exposure to hazardous goods, environmental or waste management sectors.
• CII qualifications or progress towards professional insurance qualifications.
• Previous experience meeting brokers or clients face-to-face and representing an underwriting business externally.

 

Compensation and benefits

At Gallagher, we believe supporting our colleagues goes far beyond the role itself. For more information, visit our Benefits page.

• Competitive compensation
• Comprehensive benefits programs designed to support your well-being 
• Career development opportunities and ongoing learning 
• A collaborative, people-first culture with accessible leadership 
• The opportunity to do meaningful work with global reach and local impact 

At Gallagher, we are dedicated to building an inclusive and authentic workplace. If your past experience doesn’t align perfectly, we encourage you to join our Talent Community to stay connected to additional career opportunities. Although this role is listed as full-time, if you’re in a job-share partnership, work reduced hours, or have any other flexible arrangement, please still get in touch. We will also offer reasonable adjustments to the recruitment process if required, so please let us know.

Gallagher is an affirmative action/equal opportunity employer (Minorities/Females/Veterans/Disabled)