Director of Underwriting

About the role

National Healthcare Solutions Group (NHSG), a certified "Great Place to Work," is an enterprise of specialized healthcare administration and insurance services companies. Our portfolio includes domestic companies spanning third-party employee benefits administration, pharmacy benefits management, stop loss underwriting, and PPO network solutions. With decades of industry experience, our team is united by a single mission: standing with members through every moment and milestone in their healthcare journey.

Position Summary

The Director of Underwriting leads the underwriting function and serves as a senior subject-matter expert on complex risk evaluation, pricing strategy, and portfolio performance. This role is responsible for the development, execution, and continuous improvement of underwriting strategies, guidelines, and processes that support the organization's long-term stability and growth. The Director partners closely with the SVP of Underwriting & MGU Operations to strengthen governance, modernize underwriting operations, and support enterprise-level initiatives that enhance DRM's competitiveness, credibility, and operational discipline. This role also collaborates cross-functionally with actuarial, claims, finance, sales, and external carrier and reinsurer partners to ensure underwriting outcomes align with organizational goals.

Duties and Responsibilities

• Evaluate and underwrite traditional and level-funded stop-loss products in accordance with established guidelines, policies, and authority levels.
• Assess and analyze complex risk profiles, client demographics, plan documents, and experience to determine appropriate coverage structures, pricing, and premiums.
• Ensure underwriting decisions align with company risk appetite, guidelines, and regulatory requirements.
• Contribute to portfolio performance by analyzing client experience, identifying trends, and supporting corrective action strategies.
• Support underwriting components of product development and refinement, including level-funded and emerging product opportunities.
• Mentor, train, and develop junior underwriters to strengthen underwriting judgment, consistency, and capability.
• Establish structured training programs, authority levels, and progression paths for underwriting staff.
• Provide day-to-day guidance, coaching, and oversight to ensure accuracy, timeliness, and adherence to guidelines.
• Support a collaborative, accountable, and high-performance underwriting culture.
• Lead the creation, maintenance, and enforcement of underwriting guidelines, policies, and procedures.
• Conduct or support audit cycles, evaluate adherence to guidelines, and implement corrective actions as needed.
• Partner with actuarial and leadership to refine guidelines based on performance, market trends, and audit findings.
• Ensure compliance with all applicable federal, state, and industry regulations, as well as internal policies.
• Support analysis and corrective action planning for underperforming segments, including level-funded business.
• Collaborate with actuarial to develop proactive reporting, dashboards, and performance metrics.
• Identify emerging trends, cost drivers, and opportunities to improve profitability and operational consistency.
• Contribute to strategies that strengthen reinsurer confidence and support capacity restoration.
• Partner with reinsurers and carriers to support underwriting alignment, guideline adherence, and facultative review processes.
• Provide underwriting expertise during reinsurer discussions, audits, and capacity evaluations.
• Support distribution by delivering consistent, timely, and credible underwriting decisions that strengthen broker relationships.
• Participate in client and producer meetings to communicate underwriting rationale and strategy.
• Collaborate with actuarial, claims, finance, sales, and operations to ensure comprehensive risk assessment and pricing accuracy.
• Support enterprise-level initiatives that enhance DRM's long-term stability and growth, operational discipline, and competitive positioning.
• Partner with leadership to re-envision underwriting processes, product strategy, and workflow modernization.
• Serve as a trusted advisor to the SVP of Underwriting & MGU Operations on underwriting, product, and portfolio strategy.
• Utilize digital tools, data analytics, and reporting platforms to enhance underwriting accuracy and decision-making.
• Support modernization of underwriting workflows, documentation standards, and operational efficiency.
• Provide feedback on underwriting systems, participate in testing, and support continuous improvement initiatives.
• Build and maintain relationships with brokers, TPAs, agents, and stop-loss carriers to support profitable business growth.
• Provide underwriting expertise for new and expanding client opportunities.
• Participate in client meetings and support sales efforts with clear, strategic underwriting insights.

Leadership Alignment – NHSI Capability Model

This role is expected to demonstrate the organization’s six core leadership capabilities in all areas of responsibility: Cultivate Belonging– Create inclusive and equitable hiring experiences where every candidate and employee feels valued. Drive Innovation– Introduce creative sourcing methods, leverage technology, and refine processes to strengthen talent acquisition outcomes. Execute with Excellence– Deliver measurable results in hiring velocity, quality, and retention with precision and accountability. Client-Focused Leadership– Partner with internal clients (hiring managers and leaders) to anticipate needs and exceed expectations. Navigate Strategic Change– Respond agilely to shifting business priorities, hiring demands, and market trends. Grow Talent– Serve as a talent steward who identifies, advocates for, and develops high-performing individuals across the organization.

Key Attributes for Success

• Strategic & Hands-On Execution: Balances tactical recruiting delivery with long-term workforce planning.
• Analytical & Data-Oriented: Uses insights and metrics to inform recruiting strategy and drive performance.
• Relationship Builder: Builds trust and credibility across leadership, departments, and candidates.
• Resourceful & Self-Directed: Operates autonomously and effectively in a fast-paced, high-accountability environment.
• Brand Advocate: Embodies professionalism, integrity, and service excellence in every interaction.
• Governance-Minded & Detail-Driven: Focuses on stability and growth.

Minimum Qualifications (Knowledge, Skills, and Abilities)

• Bachelor’s degree in Business, Finance, Insurance, or related field required; advanced degree preferred.
• Minimum of 7 years underwriting experience with complex risks and high-value accounts.
• Strong analytical, financial, and decision-making skills.
• In-depth knowledge of underwriting principles, risk assessment, insurance products, and regulatory requirements.
• Experience developing or maintaining underwriting guidelines strongly preferred.
• Strong negotiation, communication, and interpersonal skills.
• Proficiency in underwriting systems, data analysis tools, and Microsoft Office Suite.
• Leadership experience including mentoring or managing underwriting staff.
• Professional designations (CPCU, ARM, etc.) preferred.

Other Details

• Supervisory Responsibilities: Manages the work of individual contributors and other managers.
• Work Environment: The noise level in the work environment is usually low to moderate.
• Physical Demands: The physical demands described here are representative of those that must be met by an employee to successfully perform the essential functions of this position. Reasonable accommodations may be made to enable individuals with disabilities to perform the functions.
• Travel Requirements: Up to 30% travel as business needs require.