At a Glance
- Tasks: Manage complex commercial motor fleet accounts and underwrite new and renewal business.
- Company: Join Pen, a dynamic underwriting business backed by Gallagher.
- Benefits: Competitive pay, comprehensive benefits, and career development opportunities.
- Other info: Inclusive culture with flexible working arrangements and genuine career progression.
- Why this job: Shape the future of underwriting in a fast-paced, innovative environment.
- Qualifications: Strong experience in Commercial Motor Fleet Underwriting and risk assessment skills.
The predicted salary is between 58540 - 71548 £ per year.
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)
Senior Commercial Motor Fleet Underwriter in Leatherhead employer: Arthur J. Gallagher & Co.
At Gallagher Benefit Services, we pride ourselves on being an exceptional employer that champions a collaborative and people-first culture. As a Business Development Director in our Change & Transformation practice, you'll enjoy competitive compensation, comprehensive benefits, and ample opportunities for career development while making a meaningful impact on businesses and their employees. Join us in a dynamic environment where your ideas are valued, and you can thrive alongside a community of trusted experts and bold explorers.
StudySmarter Expert Advice🤫
We think this is how you could land Senior Commercial Motor Fleet Underwriter in Leatherhead
✨Dive Into Industry Networking Events
Get your foot in the door by attending insurance industry events and conferences. Not only will you learn about the latest trends, but you'll also meet potential employers and industry peers. Check out local chapters of professional bodies like the Chartered Insurance Institute for valuable meetups.
✨Use LinkedIn to Your Advantage
Don’t underestimate the power of LinkedIn in the insurance world. Engage with industry content, join relevant groups, and connect with professionals at companies you admire (like Arthur J. Gallagher & Co.). A thoughtful message explaining your interest can really make a difference!
✨Look Out for Graduate Schemes
Many firms in insurance have structured graduate programmes. Keep an eye on application windows and utilise your university's career services for insider tips. These schemes are designed to develop talent and often lead to permanent roles after your initial training.
✨Leverage Your Current Connections
Got friends or family in the industry? Now’s the time to reach out! Personal referrals can give you a head start, so let them know you're on the lookout for full-time opportunities at places like Arthur J. Gallagher & Co.. Don’t shy away from asking for a coffee chat; you never know what doors it might open!
We think you need these skills to ace Senior Commercial Motor Fleet Underwriter in Leatherhead
Some tips for your application 🫡
Highlight Your Analytical Skills:In insurance, we love a candidate who can crunch numbers and analyse data effectively. When crafting your CV, make sure to showcase any relevant coursework or experiences that highlight your analytical abilities, especially if you’ve tackled risk assessment or financial modelling.
Showcase Industry Knowledge:Don’t be shy about your knowledge of the insurance sector! We want to see that you've done your homework on current trends, regulations, and challenges in the industry. Mention any relevant projects or studies you’ve completed that demonstrate your understanding of the field in your cover letter.
Craft a Compelling Cover Letter:Your cover letter should tell us why you’re passionate about insurance. Share any personal experiences or what drew you into this profession. We’re looking for enthusiasm and a clear motivation for why you want to be part of our team at Arthur J. Gallagher & Co..
Tailor Your CV for the Role:Don't just send a generic CV! Focus on tailoring it specifically for the insurance role at Arthur J. Gallagher & Co.. Highlight relevant skills such as risk management, customer service experience, or any certifications you've earned in the industry to make your application stand out.
How to prepare for a job interview at Arthur J. Gallagher & Co.
✨Know Your Numbers: Insurance Fundamentals
Brush up on your understanding of key insurance concepts, like underwriting principles and risk assessment. Expect the interviewer at Arthur J. Gallagher & Co. to throw some technical questions your way, so be ready to demonstrate your grasp of these essentials.
✨Showcase Your Analytical Side
In the insurance world, it's all about data. Prepare to discuss any analytical tools or methodologies you've used in past experiences. If you have a portfolio of projects where you've tackled complex data, bring that along to impress the team!
✨Prepare for Behavioural Questions
As a full-timer at Arthur J. Gallagher & Co., they'll want to know how you handle real-life scenarios, not just theory. Think about challenges you've faced in teamwork or customer service, and how those experiences can relate to a career in insurance.
✨Know the Company Culture Inside Out
Understanding Arthur J. Gallagher & Co.'s values and workplace culture is essential. Don’t just memorise their mission statement; think about how your personal values align with theirs. This will show your genuine interest in being part of their team long-term.
