Senior/Executive Underwriter Team Lead, Small Business

About the role

We’re looking for a Senior/Executive Underwriter Team Lead, Small Business, working remotely or based in Richmond, Virginia. This role reports to the VP, Small Business Casualty Division Manager and will help drive the continued growth and evolution of Hamilton Select’s Small Business Casualty portfolio.

Responsibilities

• 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.
• 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.

Requirements

• 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.
• Able to balance profitable growth, underwriting discipline, service expectations, and business objectives.
• 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.

Qualifications

• Integrity and professionalism in all internal and external relationships.

Skills

• 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.

Benefits

At Hamilton, we offer 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
• Gym subsidy
• My day (additional days leave for personal interests/wellness/charity work)

Pay

Competitive salary with an annual performance-based target bonus.

Schedule

Hybrid working arrangement.