Director of Underwriting

Small Group Health Insurance (3–100 Employees)

Department: Underwriting & Actuarial | Reports To: CEO WellGuard Assurance

Employment Type: Full-Time, Exempt | Location: Hybrid/Remote

Company Overview

WellGuard Assurance is a Tennessee health captive insurance organization within the VerraCare healthcare eco-system. WellGuard Assurance connects small businesses with comprehensive, affordable group health coverage and partners with employers across the United States to design benefit solutions that protect their teams and support business growth.

At WellGuard Assurance, people are a greatest asset, beginning with the advisors who represent the organization in the field and help brokers, consultants, employers, and small business leaders understand coverage option

Position Summary

The Director of Underwriting provides strategic and operational leadership for the pricing, evaluation, and risk management of small employer group health insurance business (3–100 enrolled employees). WellGuard services as the underwriting and stop loss provider to small groups pooled in the captive. This individual is responsible for developing and executing rating methodologies, establishing underwriting guidelines, and ensuring that all pricing decisions align with the company's financial targets, and competitive market positioning. The Director serves as a key cross-functional partner to Actuarial, Sales, Compliance, and Product teams, and maintains consistent, data-driven decision-making across the small group book of business.

Key Responsibilities

• Rate Development & Pricing Strategy: Lead the development, maintenance, and refinement of small group manual rates and composite rating methodologies. Establish and monitor premium equivalents, trend factors, and age/gender adjustment factors in compliance with ACA single-risk-pool requirements.
• Group Analysis & Risk Assessment: Evaluate individual group submissions using both experience rating and manual rating approaches, incorporating analysis of group demographics, SIC codes, prior claims history, morbidity indicators, and benefit plan design. Determine appropriate risk loads, retention factors, and administrative cost allocations.
• Loss Ratio Management: Monitor incurred loss ratios and projected medical cost trends at the group and aggregate book level. Develop corrective pricing actions when loss experience deviates from targets, and lead quarterly and annual rate action cycles.
• Technology & AI Enhanced Method: Serve as lead and visionary for AI enhanced methods for applying rating factors to third party risk scores. Maintain regular calibration of automated processes. Manage partnerships with Gradient, Milliman, and Davies North America and provide direction for customizing/developing new processes..
• Carrier & Reinsurance Relationships: Partner with reinsurance carriers and stop-loss vendors to negotiate treaty terms and individual case rates.. Assess specific stop-loss (ISL) and aggregate stop-loss (ASL) structures for self-funded or level-funded small group products. Maintain relationships with carrier partners, wholesalers, and managing general underwriters (MGUs).
• Broker & Employer Group Relations: Serve as a senior escalation point for broker and producer inquiries on quote disputes, renewal negotiations, and coverage structure questions. Develop and maintain strong relationships with key producing agents in the small group distribution channel. Participate in finalist presentations and broker advisory panels as needed.
• Reporting & Analytics: Design and oversee production of underwriting management reports, including monthly book-of-business performance dashboards, renewal conversion rate tracking, declination analysis, and cohort-level loss experience. Present findings and recommendations to senior leadership, CEO, and Managing Partners.
• Process Improvement & Automation: Identify and implement process improvements in quoting workflows, case submission turnaround time, and decisioning consistency. Lead or sponsor technology initiatives to modernize rating engines, RFP platforms, and group management systems.
• Product & Benefit Design Collaboration: Collaborate with Product Development and Actuarial on the introduction of new benefit designs, plan structures, and network configurations, providing underwriting perspective on risk implications and premium impact. Support competitive analysis and market benchmarking.
• Underwriting Guideline Governance: Author, maintain, and periodically review the company's small group underwriting manual and risk selection guidelines. Ensure guidelines are applied consistently across the underwriting team and are updated to reflect changes in risk environment, regulatory landscape, or company strategy.

Required Qualifications

Education

• Bachelor's degree in Business Administration, Finance, Mathematics, Actuarial Science, Healthcare Administration, or a related quantitative field.

Experience

• Minimum of 5 years of progressive underwriting experience in health insurance, with at least 3 years focused on the small group market (employer groups of 2–100 employees).
• Minimum of 3 years in a underwriting leadership role, including direct supervisory responsibility for underwriting staff.
• Demonstrated hands-on experience with both manual rating and experience rating methodologies for fully insured small group medical plans.

Technical & Domain Skills

• Proficiency with rate development tools and actuarial data models; ability to build and interrogate Excel-based pricing models (advanced functions, pivot tables, scenario analysis).
• Familiarity with medical cost trend drivers, morbidity analysis, and utilization management concepts (inpatient, outpatient, pharmacy, behavioral health).
• Working knowledge of reinsurance structures including specific stop-loss (ISL), aggregate stop-loss (ASL), and surplus lines products applicable to self-funded small groups.
• Experience interpreting and applying HIPAA, state insurance regulations, DOL rules, and CMS guidance as applicable to the small group underwriting function.

Preferred Qualifications

• Master's degree (MBA, MHA, or MS in Actuarial Science) or equivalent advanced professional credential.
• Associate of the Society of Actuaries (ASA) designation, Fellowship (FSA), or progress toward ACAS/FCAS credentials.
• Certified Healthcare Financial Professional (CHFP) or Fellow of the Health Plan Association (FHPA).
• 8 years ars of health insurance underwriting experience, including exposure to level-funded and administrative services only (ASO) products for small groups.
• Experience working within a health plan, , regional HMO, or managed care organization in a small-to-mid-size group underwriting capacity.
• Familiarity with underwriting information systems and group management platforms (e.g., Sail, Curve, Salesforce Health Cloud, or equivalent).
• Experience with business intelligence and data visualization tools such as Tableau, Power BI, or SQL-based reporting environments.
• Exposure to ancillary benefits underwriting (dental, vision, life, disability) in support of packaged small group product offerings.

Key Competencies

• Analytical Rigor: Ability to synthesize large volumes of claims, demographic, and financial data into clear, actionable underwriting conclusions; strong command of statistical reasoning and probability concepts.
• Strategic Thinking: Ability to connect individual group underwriting decisions to portfolio-level financial outcomes and company strategy; forward-looking perspective on market trends, competitive dynamics, and regulatory shifts.
• Leadership & People Development: Proven ability to build high-performing underwriting teams, provide constructive feedback, set stretch goals, and cultivate technical expertise at all levels of the team.
• Decision-Making Under Uncertainty: Comfort with making sound risk selection and pricing decisions using incomplete information; ability to document and defend underwriting rationale consistently.
• Regulatory Acumen: Strong command of ACA small group market regulations and state insurance department requirements; ability to translate regulatory changes into actionable underwriting policy updates.
• Stakeholder Communication: Ability to communicate complex actuarial and underwriting concepts clearly to non-technical audiences including senior leadership, brokers, and employer clients.
• Attention to Detail: High degree of accuracy in rate calculations, guideline interpretation, and compliance documentation; strong written and verbal communication skills.
• Collaborative Influence: Ability to drive cross-functional alignment with Actuarial, Sales, Product, Compliance, and Finance teams without direct authority.

Pay: $150,000.00 - $180,000.00 per year

Benefits:

• 401(k) matching
• Dental insurance
• Employee assistance program
• Health insurance
• Life insurance
• Paid time off
• Vision insurance

Work Location: Remote