Senior Director, Underwriting

Trustmark; Chicago (IL); On-site; USD 108,000 - 161,000; Full time

Benefits offered by this job

Health/dental/vision

Life insurance

401(k) plan

Wellness program

Back-up Care for Children, Adults andE

Job summary

Trustmark, headquartered in the United States, seeks an experienced Head of Underwriting to lead production underwriting and operations for small group and level-funded portfolios. You will shape strategy, drive scalable processes, and partner with sales to support growth and profitability.

You will develop the team, implement data-driven insights, and collaborate across actuarial, product, and technology to ensure quality and efficiency in underwriting.

Qualifications

• Bachelor’s degree in business, finance, actuarial science, or related field.
• 8+ years of underwriting experience in health insurance, focusing on small group 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 operations staff.
• Experience designing, implementing, and optimizing underwriting processes, workflows, and operational improvements.
• Strong analytical skills with data, reporting, and performance metrics to drive decisions.
• Demonstrated success partnering with sales teams, including aligning underwriting strategies to support growth and improve close rates.

Responsibilities

• Leads production underwriting to ensure disciplined risk selection, pricing consistency, and growth & profitability targets across small group and level-funded business.
• Shapes underwriting strategy by designing scalable processes, tools, and workflows to improve efficiency and risk assessment.
• Partners with sales leadership to align underwriting execution with growth objectives and coaches field engagement.
• Oversees underwriting operations and ensures efficient case flow, service levels, and high-quality submission handling.
• Builds and develops a high-performing underwriting team through coaching, performance mgmt, and capability development.
• Collaborates with actuarial, product, and operations teams to align pricing, risk management, and business strategy.

Skills

Underwriting leadership

Data analysis

Stakeholder management

Pricing discipline

Portfolio management

Team development

Sales collaboration

Process optimization

Communication

Education

Bachelor's degree in business, finance, actuarial science, or related field

Job description

Trustmark’s mission is to improve wellbeing – for everyone. It is a mission grounded in a belief in equality and born from our caring culture. It is a culture we can only realize by building trust. Trust established by ensuring associates feel respected, valued and heard. At Trustmark, you’ll work collaboratively to transform lives and help people, communities and businesses thrive. Flourish in a culture of diversity and inclusion where appreciation, mutual respect and trust are constants, not just for our customers but for ourselves. At Trustmark, we have a commitment to welcoming people, no matter their background, identity or experience, to a workplace where they feel safe being their whole, authentic selves. A workplace made up of diverse, empowered individuals that allows ideas to thrive and enables us to bring the best to our colleagues, clients and communities.

About The Role

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.

Key Accountabilities

• Underwriting Leadership and Portfolio Performance: 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.
• Underwriting Strategy and Process Innovation: 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.
• Sales Partnership Effectiveness: 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.
• Underwriting Operation Oversights: 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.
• Talent Development and Team Leadership: 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.
• Cross Functional Collaboration: 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.

Minimum 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).

Preferred

• 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.

The compensation range for this role is (based on the corporate location in Lake Forest, Illinois):

$107,546 - $160,583 per year

The final salary offer will be determined based on factors such as location, qualifications, experience, skill set, and other relevant factors. This position may also be eligible for bonus. We understand that compensation is an important factor when considering a new opportunity, and we strive to provide a competitive salary within the market.

Brand: Trustmark

• In addition to compensation, we offer a comprehensive benefits package that includes: Health/dental/vision, life insurance, FSA and HSA, 401(k) plan, Employee Assistant Program, Back-up Care for Children, Adults and Elders and many health and wellness initiatives.
• We also offer a Wellness program that enables employees to participate in health initiatives to reduce their insurance premiums.

Trustmark is committed to leveraging the talent of a diverse workforce to create great opportunities for our people and our business. We are an equal opportunity employer, including disability and protected veteran status.