Senior Director, Risk & Insurance Strategy

CarMax Business Services; Richmond (VA); On-site; USD 112,000 - 179,000; Full time

Job summary

CarMax is seeking a Risk Manager in Richmond, VA to shape the risk and insurance program that supports over 250 retail locations and about 30,000 associates. You will oversee Workers’ Compensation, Auto and General Liability, Property, and related programs, partnering with actuaries and insurers to protect the Company’s financial security.

The role requires strategic leadership, budget stewardship, and the ability to drive underwriting submissions and complex claims decisions with senior

Qualifications

• 8+ years of risk management experience in a large company with multiple lines of insurance.
• Fluency in insurance markets, products, and terminology.
• Proficient in Microsoft Office (Excel, Word, PowerPoint, Outlook).
• Ability to motivate and influence across multiple levels of the organization.
• Strong relationship-building and negotiation skills.
• Ability to manage multiple projects and prioritize effectively.
• Analytical mindset to drive informed risk decisions.

Responsibilities

• Identify, evaluate, and manage risks across CarMax’s operations to reduce exposure.
• Lead strategy for commercial insurance programs including Auto Liability, General Liability, WC, Property, and more.
• Develop underwriting submissions and drive renewals and insurer negotiations.
• Analyze program effectiveness to align with exposures and risk tolerance.
• Lead Workers’ Compensation strategy and oversee WC associates and claims.
• Oversee Bermuda-based captive insurance company and related compliance.
• Cultivate relationships with actuaries, auditors, brokers, insurers, and counsel.
• Direct strategy and authority for litigated or complex claims with legal counsel.
• Prepare annual budget and present forecasts to Executive Leadership.
• Provide insurance updates to the Board/Audit Committee and support SOX controls.
• Support 250+ store locations with certificates, cards, inquiries, and guidance.

Skills

Risk management experience

Insurance knowledge

MS Office

Stakeholder influence

Relationship building

Negotiation

Project management

Analytical thinking

Education

Bachelor's degree

Job description

CarMax is seeking a Risk Manager in Richmond, VA to shape the risk and insurance program that supports over 250 retail locations and about 30,000 associates. You will oversee Workers’ Compensation, Auto and General Liability, Property, and related programs, partnering with actuaries and insurers to protect the Company’s financial security.

The role requires strategic leadership, budget stewardship, and the ability to drive underwriting submissions and complex claims decisions with senior