Middle Market Underwriting Leader

About the role

The Middle Market Underwriting Leader role provides leadership and oversight for the Middle Market underwriting team. The role includes providing guidance on evaluating, pricing, and managing complex risks, driving development to remain competitive, and monitoring performance and claims trends to inform actionable strategies.

Responsibilities

• Leads and oversees Middle Market underwriting, guiding a team to effectively evaluate, price, and manage complex risks while modeling strong underwriting judgment.
• Drives development to remain competitive and monitors performance and claims trends to inform actionable strategies that support sustainable growth and portfolio stability.
• Accountable for P&L results, manages key metrics, and implements corrective actions as needed.
• Fosters a culture of accountability and excellence through coaching, audits, and governance of underwriting authority.
• Collaborates cross-functionally with Distribution, Claims, Pricing, and Risk Management, while building strategic partnerships to drive profitable growth.
• Contributes to identifying emerging risks and opportunities, balancing strategic vision with operational leadership.
• May lead other underwriting segments, such as Programs and/or Excess and Surplus Lines.
• Leads the Middle Market underwriting portfolio, driving disciplined growth, execution, and sustained performance through strategic portfolio management.
• Directs the Middle Market strategy, translating company objectives into actionable plans for the portfolio.
• Oversees and optimizes the operational performance of the Middle Market portfolio, driving alignment with profitability, risk appetite, and regulatory requirements while identifying and implementing improvements to enhance portfolio outcomes.
• Designs and drives training programs to enhance team capabilities, aligning development efforts with performance goals and business needs.
• Understands the Middle Market marketplace and agent and customer expectations.
• Participates in Guidelines Leadership Team to develop underwriting guidelines.
• Models effective leadership, motivating the team to achieve shared goals while reinforcing professionalism and accountability.
• Recruits, trains, coaches, and develops underwriting staff.
• Conducts goal-setting activities and individual performance reviews.
• Manages department workflow to ensure proper controls and procedures are documented, maintained, and followed.
• Establishes workload and territory assignments and monitors productivity.
• Collaborates with the VP, Underwriting to shape and execute the Middle Market strategy, translating company objectives into actionable plans for the portfolio.
• Ensures compliance with underwriting guidelines, authority levels, company policies, and regulatory requirements.
• Maintains expenses at or below budget for assigned team.
• Drives innovation and capability enhancements in portfolio management, AI utilization, underwriting processes, and performance metrics by identifying opportunities, developing recommendations, and leading implementation.
• Uses data and analytics to inform decisions, identify trends, and improve underwriting practices.
• Stays informed on industry trends, emerging risks, and competitor offerings to enhance underwriting effectiveness.
• May underwrite complex Middle Market business.

Requirements

• Thorough knowledge of principles and practices of commercial insurance underwriting.
• Expert knowledge of commercial policy language.
• Expertise in building and maintaining relationships with distribution partners and individual account negotiations.
• Ability to develop, build, and lead highly-effective teams.
• Demonstrated experience in influencing and leading teams of underwriters.
• Knowledge of employee management principles including hiring, supervision, training, retention, and performance evaluation.
• Ability to develop a plan and execute it.
• Ability to make timely decisions independently, using personal knowledge and discretion.
• Ability to organize and prioritize work.
• Strong interpersonal skills.
• Deep problem-solving skills.
• Work independently and use initiative.
• Possess critical thinking skills and sound judgment in underwriting decisions.
• Determine when and how to escalate concerns.
• Ability to understand and apply laws, rules and regulations.
• Ability to deal with confidential information.
• Establish and maintain effective working relationships with those contacted in the course of work.
• Interact externally and internally with professionalism and confidence.
• Possess a high level of executive functioning skills to organize and prioritize work.
• Meet finite deadlines and deal with pressure situations.
• Maintain records; prepare reports/correspondence related to the work.
• Communicate and work effectively with others (oral and written).
• Correct English usage, spelling, grammar, vocabulary and punctuation.
• Knowledge of management information and business systems such as Word, Excel, PowerPoint etc.
• Utilize computer and related software effectively.

Qualifications

• High School Diploma or equivalent and 20 years of related experience with at least 5 in leadership; or Associate’s Degree or equivalent and 15 years of related experience with at least 3 in leadership; and One of the following industry related certifications: Chartered Property Casualty Underwriter (CPCU), or Certified Insurance Counselor (CIC) OR Bachelor’s Degree and 8 years of related experience with at least 2 in leadership; or Master’s Degree and 6 years of related experience with at least 1 in leadership
• Bachelor’s Degree and 10 years of related experience with at least 5 years in leadership; or Master’s Degree and 8 years of related experience with at least 3 years in leadership