Vice President Medical Stop Loss Underwriting Operations - Chicago, IL (60606)

Vice President Medical Stop Loss Underwriting Operations Location: Chicago, IL (hybrid) Compensation: $160,000 - $200,000 (depending on experience) About the role We are seeking an experienced and strategic Vice President of Medical Stop Loss Underwriting Operations to lead all operational aspects of our growing medical stop loss portfolio.

In this high-impact role, you'll be responsible for ensuring efficient policy issuance, premium application, enrollment administration, and regulatory compliance — all while managing a team of dedicated account managers and analysts.

You'll work closely with senior leadership, underwriting teams, and cross-functional partners to streamline processes, reduce cycle times, and deliver a high-quality experience for brokers, TPAs, and clients.

This position is ideal for a collaborative leader with deep expertise in medical stop loss underwriting operations, a passion for team development, and a strong understanding of compliance and regulatory frameworks.

What You'll Do Lead and oversee all aspects of underwriting operations for Medical Stop Loss insurance, including: Policy issuance Premium application Enrollment variance identification Manage and mentor a team of account managers and premium & enrollment professionals Collaborate with underwriting, legal, compliance, and senior leadership to ensure regulatory alignment and operational consistency Identify and implement process improvements to increase accuracy, reduce cycle times, and enhance the client experience Maintain high standards for compliance, ensuring all activities meet state and federal requirements and align with company underwriting guidelines Drive performance tracking and reporting for underwriting operations KPIs What Makes You a Great Fit Bachelor's degree in Business, Finance, Insurance, or related field 8+ years of medical stop loss underwriting experience, including 3+ years in a leadership or operational management role Deep knowledge of stop loss products, underwriting guidelines, policy issuance, and premium administration Proven success leading high-performing teams in a fast-paced, regulated environment Strategic mindset with strong analytical, problem-solving, and process optimization capabilities Strong communication and collaboration skills across all levels of the organization Compensation & Benefits $160,000 to $200,000 (depending on experience) Enjoy a hybrid work environment with flexible scheduling and a supportive company culture Competitive executive compensation package with strong benefits, career development support, and leadership visibility