Senior/Executive Underwriter Team Lead, Small Business

We’re looking for a Senior/Executive Underwriter Team Lead, Small Business Working remotely or based in Richmond, Virginia and reporting to the VP, Small Business Casualty Division Manager, this role will help drive the continued growth and evolution of Hamilton Select's Small Business Casualty portfolio. This position is ideal for an experienced E&S casualty underwriter who combines strong technical underwriting expertise with a portfolio management mindset. As Hamilton continues to invest in advanced underwriting technology, automation, and AI-enabled workflows, this role will focus on managing broker portfolios, underwriting performance, distribution strategy, and profitable growth across a diversified book of hard-to-place casualty business. While there is a preference to be based in Richmond, VA, we are open to a remote working location for appropriately qualified candidates. Hamilton Select is our U.S. excess and surplus lines insurer based in Richmond, Virginia, underwriting hard-to-place accounts in the small and middle-market space through an appointed wholesale broker network. The successful candidate will be responsible for developing and managing wholesale broker relationships, optimizing portfolio performance, identifying growth opportunities, and ensuring underwriting discipline while delivering exceptional service to our trading partners. This role will include occasional business travel. What you will do: Underwrite complex and challenging Excess & Surplus casualty risks, including contractors, real estate, hospitality, habitational, and other small business classes. Manage wholesale broker portfolios to achieve profitable growth, strong service outcomes, and disciplined underwriting execution. Contribute to the growth and diversification of Hamilton's Small Business portfolio through thoughtful distribution, appetite, and class management. Maintain underwriting standards and portfolio discipline that support profitable results and consistent decision-making. Monitor performance across brokers, classes, territories, and distribution channels to identify trends, opportunities, and corrective actions. Use data, analytics, and underwriting insights to improve efficiency, profitability, and overall portfolio performance. Apply sound underwriting judgment within Hamilton's technology-enabled environment to support timely, consistent, and portfolio-aware decisions. Champion technology, automation, and workflow improvements that enhance underwriting efficiency and ease of doing business. Develop high-level wholesale broker relationships through effective communication, market engagement, and occasional business travel. Use critical thinking and underwriting expertise to negotiate coverage, pricing, terms, and conditions. Partner with technology, product, actuarial, and claims teams to improve strategy, workflow, and portfolio performance. Train, mentor, and support the development of underwriters. Ensure compliance with applicable letters of underwriting authority, state rules, and regulatory requirements. Support special projects, corporate initiatives, and strategic efforts aligned with Small Business objectives. What we’re looking for in the role: 5+ years of casualty underwriting experience, preferably within the Excess & Surplus marketplace. Strong technical underwriting expertise in casualty and liability lines. Proven ability to manage profitable books of business through disciplined underwriting, portfolio management, and broker relationship development. Experience underwriting difficult-to-place risks and identifying account- and portfolio-level opportunities. Strong understanding of broker segmentation, appetite management, growth strategy, and profitability measurement. Ability to balance profitable growth, underwriting discipline, service expectations, and business objectives. Ability to attract business through existing broker relationships while developing new distribution opportunities. Sound underwriting judgment, including the ability to assess both subjective and objective risk factors and justify decisions at all levels of the organization. Experience using underwriting technology, data analytics, predictive tools, or automated underwriting solutions to improve business outcomes. Broad understanding of E&S market trends, competitive dynamics, and emerging risks. Integrity and professionalism in all internal and external relationships. Other Personal Attributes: Motivated self-starter with an entrepreneurial mindset. Strong portfolio management and business acumen. Excellent verbal and written communication skills. Proven decision-making skills and underwriting judgment. Strong coaching, mentoring, and relationship management abilities. Approachable and effective at marketing business and developing broker partnerships. Keen attention to detail, highly analytical, and excellent problem-solving capability. Demonstrates an understanding and capacity to effectively engage in negotiations and influence outcomes. Ability to interpret underwriting and performance data and translate insights into actionable business strategies. Comfortable operating in a technology-enabled underwriting environment where human judgment, portfolio management, and broker engagement drive success. Dedicated, collaborative, and results-oriented. What you can expect from us At Hamilton, we offer a vibrant, entrepreneurial and collaborative workplace shaped by our values: Be Smart, Be Sensible, Be Open and Be More. Our employees consistently say they would recommend Hamilton as a great place to work — a testament to the inclusive, supportive, and empowering culture we’ve built together. We embrace individuality, value diverse perspectives, and recognise the unique contribution each person makes to our continued success. Hamilton offers a competitive salary with an annual performance-based target bonus and a comprehensive benefits package, to include: Hybrid working Matching 401K plan Medical, dental, vision, life, disability Generous time off (including parental leave) Continued support for professional development Gym subsidy My day (additional days leave for personal interests/wellness/charity work In good company. Hamilton (NYSE: HG) underwrites specialty insurance and reinsurance risks on a global basis through its wholly owned subsidiaries. Its three underwriting platforms: Hamilton Global Specialty, Hamilton Select and Hamilton Re, each with dedicated and experienced leadership, provide access to diversified and profitable business around the world. Headquartered in Bermuda, Hamilton has over 600 employees with key underwriting operations in London, Bermuda, the US and Dublin. We work collaboratively, we share a passion for the service and results we deliver, and we know that what we do each day is meaningful – to our customers and our business. We believe we are ‘In good company.’ with everyone we interact with.