Director of Underwriting

The Champlain Insurance Group (“CIG” or “the Company”) is a fast-growing specialty surplus and excess lines insurance enterprise. Through our affiliates—Champlain Specialty Insurance Company, WestCongress Insurance Services LLC, and WestCongress Risk Services LLC—we offer primary and excess general liability insurance solutions and claims administration throughout the United States. We are seeking a Director of Underwriting to join our team in Boston, MA.

Summary:

The Director of Underwriting serves as a senior leader responsible for underwriting strategy execution, risk management oversight, pricing integrity, and portfolio performance. This role is accountable for translating underwriting philosophy into operational excellence, ensuring profitable growth, and maintaining disciplined risk selection aligned with corporate objectives. The Director partners closely with executive leadership to balance growth, profitability, and compliance while fostering a culture of sound risk assessment and continuous improvement.

Responsibilities:

Strategic Leadership

• Execute the organization’s underwriting strategy in alignment with business growth and profitability goals.
• Establish and maintain underwriting policies, guidelines, and authorities to ensure consistent risk selection and portfolio performance.
• Provide market insights related to competitive positioning and emerging risk trends.
• Partner with Product, Actuarial, and Finance teams to support pricing frameworks that reflect accurate risk assessment.

Operational Excellence

• Lead and oversee underwriting operations, ensuring high-quality and timely decision-making across all lines of business.
• Implement underwriting governance, audit processes, and performance metrics to maintain portfolio health.
• Continuously evaluate underwriting processes and technology to drive efficiency, automation, and scalability.
• Support reinsurance strategies and relationships to optimize risk transfer and capital utilization.

Risk Management & Compliance

• Ensure adherence to regulatory requirements, internal policies, and established risk appetite frameworks.
• Collaborate with Risk, Legal, and Compliance teams to monitor emerging risks and support mitigation strategies.
• Lead regular portfolio reviews to assess risk exposure, concentration, and underwriting profitability.

Leadership & Talent Development

• Build, mentor, and manage a high-performing underwriting team with strong analytical and decision-making capabilities.
• Promote cross-functional collaboration with distribution, claims, and product teams.
• Foster a culture of accountability, professional development, and continuous learning.

Qualifications:

• Bachelor’s degree in Finance, Business, Economics, Risk Management, or related field (Master’s preferred).
• Minimum 10–15 years of progressive underwriting experience, including 5 years in a leadership or management role.
• Proven success in underwriting operations, portfolio management, and risk governance.
• Strong understanding of market dynamics, risk modeling, and financial performance drivers.
• Excellent leadership, communication, and analytical skills.
• Professional certifications such as CPCU, ARM, or equivalent are strongly preferred.

Competencies:

• Strategic Thinking & Decision-Making
• Financial & Risk Acumen
• Data-Driven Leadership
• Change & Innovation Management
• Stakeholder Collaboration
• Talent Development

Opportunity for Advancement

For the successful candidate who demonstrates strong performance and a desire to grow, this role may offer opportunities for advancement to positions of increasing responsibility and authority within CIG’s insurance enterprise.

Compensation:

We offer a competitive compensation package, including bonus opportunity, health, dental, vision, life, and disability insurance, matching 401(k), paid time off, and holidays.