Director of Underwriting - Remote

Overview

The Director of Underwriting will lead Sidecar Health’s group underwriting function while also serving as a hands-on contributor. This role is both a player-coach and a growth partner, directly underwriting complex, high-value cases while managing, mentoring, and developing a team of underwriters.

In Short

• Lead and contribute to the underwriting of large and complex group cases.
• Manage and mentor a team of group underwriters.
• Establish underwriting guidelines balancing competitiveness, risk, and profitability.
• Support new business growth in collaboration with Sales.
• Provide creative underwriting solutions.
• Collaborate with various departments to inform pricing strategies.
• Review and approve escalated underwriting decisions.
• Monitor underwriting performance and implement corrective actions.
• Build relationships with brokers and consultants.
• Promote a culture of accountability and continuous improvement.

Requirements

• 8+ years of experience in group underwriting within health insurance.
• Proven ability as a “player-coach” in underwriting.
• Success in partnering with Sales to win new business.
• Deep knowledge of underwriting methodologies and healthcare cost drivers.
• Strong analytical and problem-solving skills.
• Excellent communication and relationship-building skills.
• Familiarity with reinsurance markets preferred.
• Comfortable in a fast-paced, high-growth environment.
• Bachelor’s degree.

Benefits

• Competitive salary, bonus opportunity, and equity package.
• Comprehensive Medical, Dental, and Vision benefits.
• A 401k retirement plan.
• Paid vacation and company holidays.
• Opportunity to make an impact at a rapidly growing company.