Underwriting Manager, Middle Market, Berkshire United

Regional Middle-Market Underwriting Operation Leader

This is an opportunity to build and lead a regional middle-market underwriting operation with responsibility for a multiline admitted property and casualty portfolio. The role combines people leadership, portfolio management, broker relationship development, technical underwriting leadership, and business-building responsibilities.

The (AVP or VP) Underwriter in this role will develop a high-performing underwriting team, establish and execute regional underwriting and broker strategies, and drive profitable portfolio growth. The position requires a leader who can balance strategic direction with hands-on execution while establishing the structure, practices, and market relationships needed to support sustainable growth. Title and level may be aligned to experience and qualifications.

Key Responsibilities:

• Build and lead a regional underwriting organization, including recruiting, onboarding, developing, and retaining experienced multiline underwriters.
• Own the strategy, profitable growth, and overall performance of a multiline admitted property and casualty portfolio.
• Establish production, profitability, retention, and portfolio objectives; monitor results and pipeline activity; and take appropriate action to maintain disciplined execution.
• Provide technical underwriting leadership across risk selection, exposure evaluation, pricing, terms, account structure, referrals, and underwriting authority.
• Develop and execute a regional retail broker strategy that strengthens key relationships and generates profitable new and renewal opportunities.
• Coach and develop underwriters through ongoing feedback, account consultation, performance management, and individualized development planning.
• Maintain underwriting quality through portfolio reviews, file audits, referral oversight, and consistent application of underwriting guidelines, authorities, and standards.
• Partner across Distribution, Claims, Risk Engineering, and other functions to deliver coordinated solutions and improve the broker and customer experience.
• Translate regional insights into recommendations that strengthen underwriting strategy, operating practices, and business execution.

Key Skills:

• People Leadership: Ability to build, develop, coach, and retain experienced underwriting teams while establishing clear expectations and accountability.
• Multiline Underwriting Expertise: Strong technical capability across Property, General Liability, Commercial Automobile, Workers Compensation, Umbrella/Excess, and Inland Marine.
• Portfolio Management: Ability to manage production, profitability, retention, risk selection, underwriting quality, and referral activity to achieve portfolio objectives.
• Broker Relationship Management: Demonstrated ability to develop productive retail broker relationships and expand market presence.
• Underwriting Judgment: Strong decision-making capabilities across risk selection, pricing, exposure evaluation, terms, structure, and underwriting authority.
• Strategic Execution: Ability to translate business objectives and market insights into practical strategies and measurable execution.
• Team Building: Ability to establish structure and build effective teams within an entrepreneurial and growing environment.
• Analytical Thinking: Ability to evaluate portfolio performance and balance growth opportunities with underwriting discipline.
• Communication and Influence: Strong communication, negotiation, presentation, and relationship-management skills with the ability to influence across functions and organizational levels.

Qualifications:

• Minimum of 10 years of commercial property and casualty underwriting experience, including significant experience within the admitted middle-market segment.
• Minimum of 3 years of demonstrated people-leadership experience, including recruiting, coaching, performance management, and development of experienced underwriters.
• Broad underwriting experience across Property, General Liability, Commercial Automobile, Workers Compensation, Umbrella/Excess, and Inland Marine.
• Demonstrated track record of driving profitable portfolio performance through disciplined production management, risk selection, underwriting quality, and referral oversight.
• Experience building and maintaining productive relationships with retail brokers; established relationships within Chicago and the Western Region are preferred.
• Demonstrated ability to build teams and establish effective operating structures within a growing business environment.
• Bachelors degree preferred.
• CPCU or another relevant professional designation is a plus.

BHSI Offers:

• A competitive package and exciting growth opportunities for career-oriented teammates.
• A dynamic, action-oriented, and thoughtful environment centered on always doing the right thing for our customers, teammates, and other stakeholders.
• A purposely non-bureaucratic organization that embraces simplicity over complexity and emphasizes individual excellence in a team framework.
• Benefits that support your life and well-being, which include:
• Comprehensive Health, Dental and Vision benefits.
• Disability Insurance (both short-term and long-term).
• Life Insurance (for you and your family).
• Accidental Death & Dismemberment Insurance (for you and your family).
• Flexible Spending Accounts.
• Health Reimbursement Account.
• Employee Assistance Program.
• Retirement Savings 401(k) Plan with Company Match.
• Generous holiday and Paid Time Off.
• Tuition Reimbursement.
• Paid Parental Leave.

The base salary range for this position is $150,000 to $225,000, along with annual bonus eligibility. Total compensation for a candidate is determined by their relevant skills, location, and experience. We value our teammates both their capabilities and character as demonstrated by our amazing culture.

NOTE: Compensation will be commensurate with experience. This job description is not intended to be all-inclusive. Team Member may perform other related duties as negotiated to meet the ongoing needs of the organization.