Underwriting Analyst (Stop Loss Insurance) – Remote or Hybrid Chicago Suburbs, IL Full-Time | $60,000 – $70,000 We are seeking a detail-oriented and analytically driven Underwriting Analyst to join a growing Stop Loss underwriting team supporting complex risk assessment and pricing decisions in a fast-paced, collaborative environment. This role plays a critical part in the underwriting process by ensuring the accuracy of submitted data, validating risk parameters, and supporting underwriting decisions through detailed analysis and documentation. The ideal candidate is comfortable working with large data sets, highly proficient in Excel, and interested in developing a long-term career within health insurance and stop loss underwriting. Reporting to the AVP, Underwriting – Life & Health, this position works closely with Underwriters, Actuaries, and Sales partners to ensure consistent underwriting standards and high-quality risk selection.

Key Responsibilities

• Review submitted underwriting data for accuracy and completeness
• Validate quote inputs and ensure adherence to underwriting guidelines prior to release
• Analyze expense assumptions and ensure proper system setup
• Review state and regulatory requirements for compliance considerations
• Set up and evaluate experience data for underwriting analysis
• Summarize large claim data to identify risk indicators and trends
• Support risk evaluation for stop loss and self-funded health plans
• Prepare underwriting summaries and group write-ups for senior review
• Maintain accurate underwriting records and ensure data integrity across systems

Qualifications

• Bachelor’s degree preferred in Finance, Economics, Business, Actuarial Science, or related field
• 2–4 years of experience in insurance, ideally within stop loss, health insurance, or self-funded plans
• Strong Excel skills required (pivot tables, VLOOKUP/XLOOKUP, data analysis)
• Exposure to underwriting systems, databases, or rating tools preferred
• Progress toward insurance designations (AU, AINS, CPCU, HIA, FLMI) a plus
• Strong analytical mindset with excellent attention to detail

This is a great opportunity for someone looking to build deep expertise in stop loss underwriting while working alongside experienced industry professionals in a high-growth environment. Please reach out to Kyle Archer at [email protected] if interested. #LI-KA1 #LI-Hybrid Remote Skills: Actuarial Skills, Analysis Skills, Data Analysis, Data Quality, Data Sets, Detail Oriented, Documentation, Economics, Finance, Health Insurance, Health Plan, Insurance, Maintain Compliance, Microsoft Excel, Partner Sales, Pivot Tables, Pricing, Record Keeping, Regulatory Compliance, Regulatory Requirements, Risk, Risk Analysis, State Laws and Regulations, Stop Loss Insurance, Team Player, Underwriting, Vlookups About the Company: Daley and Associates Daley And Associates, LLC (“DAA”) is a boutique search, executive, and contract staffing firm located in Boston, MA. We specialize in the placement of Accounting, Finance, Information Technology, Legal, Administrative, and Life Sciences professionals at all levels. The firm was founded in 2005 by distinguished executives with over 30+ years of staffing agency experience with the mission to create a different kind of recruiting firm, one that provides a very hands-on, consultative approach to the clients they serve. Daley And Associates works with some of the most prominent businesses in the greater Boston area. Our clients range from promising start-ups to Fortune 100 companies. Company Size: 20 to 49 employees Industry: Staffing/Employment Agencies Founded: 2005 Website: http://daleyaa.com/