Senior Director, Underwriting

Trustmark • Lake Forest, IL

1d • $107,546 - $160,583

About The Position

Leads production underwriting and underwriting operations for small group and level-funded business, ensuring disciplined growth, consistent risk selection, and operational excellence. Manages production underwriters and underwriting operations leadership while shaping underwriting strategy through the design and implementation of scalable processes and workflows. Develops and reports on data driven insights to improve effectiveness. As a key partner to sales, ensures alignment on growth objectives and coaches team members on effective sales staff engagement. Collaborates with actuarial, product, operations, and technology teams to ensure alignment of processes, risk management, and business strategy. Accountable for underwriting quality, team development, process innovation/efficiency, and achieving profitable growth across the portfolio.

Requirements

• Bachelor’s degree in business, finance, actuarial science, or a related field.
• 8+ years of underwriting experience in health insurance, with a strong focus on small group and/or level-funded products.
• 2+ years of leadership experience, including direct management of underwriting teams and/or team leaders.
• Demonstrated expertise in underwriting risk assessment, pricing discipline, and portfolio management.
• Proven ability to lead and develop high-performing teams, including both production underwriters and operational support functions.
• Experience designing, implementing, and optimizing underwriting processes, workflows, and operational improvements.
• Strong analytical skills with experience leveraging data, reporting, and performance metrics to drive decisions and outcomes.
• Demonstrated success partnering with sales teams, including aligning underwriting strategies to support growth and improve close rates.
• Deep understanding of underwriting systems, case management workflows, and service-level performance expectations.
• Excellent communication, influencing, and stakeholder management skills across cross-functional teams (e.g., sales, actuarial, operations).

Nice To Haves

• Experience with level-funded or alternative funding arrangements.
• Background working closely with actuarial pricing or analytics teams.
• Exposure to underwriting automation, digital tools, or AI-driven processes.

Responsibilities

• Leads production underwriting to ensure disciplined risk selection, pricing consistency, and achievement of growth and profitability targets across small group and level-funded business.
• Establishes underwriting guidelines and leverages performance reporting, analytics, and portfolio insights to monitor results, identify trends, and drive accountability across the team.
• Shapes underwriting strategy by identifying opportunities to improve outcomes through the design and implementation of new processes, tools, and workflows.
• Drives scalable, repeatable approaches that enhance efficiency, risk assessment, and consistency, while adapting to market dynamics.
• Partners closely with sales leadership to align underwriting execution with growth objectives.
• Serves as a subject matter expert in underwriting-sales collaboration and coaches team members on effective field engagement, positioning, and deal support to improve close rates and field confidence.
• Oversees underwriting operations through direct management of operations leadership.
• Ensures efficient case flow, service level performance, and high-quality submission handling.
• Aligns operational processes with underwriting objectives to reduce friction and improve throughput.
• Builds and develops a high-performing underwriting team through coaching, performance management, and capability development.
• Establishes clear expectations, fosters accountability, and develops future leaders across both production underwriting and operations.
• Partners with actuarial, product, and operations teams to ensure alignment on pricing, risk management, and business strategy.
• Supports governance processes, contributes to performance reviews, and ensures underwriting practices are consistent with enterprise objectives.

Benefits

• Health/dental/vision
• life insurance
• FSA and HSA
• 401(k) plan
• Employee Assistant Program
• Back-up Care for Children, Adults and Elders
• many health and wellness initiatives
• Wellness program that enables employees to participate in health initiatives to reduce their insurance premiums.

What This Job Offers

• Job Type: Full-time
• Career Level: Senior