Director, Insurance & Risk

Be part of an amazing story.

Macy’s is more than just a store. We’re a story. One that’s captured the hearts and minds of America for more than 160 years. A story about innovations and traditions…about inspiring stores and irresistible products…about the excitement of the Macy’s 4th of July Fireworks, and the wonder of the Thanksgiving Day Parade. We’ve been part of memorable moments and milestones for countless customers and colleagues. Those stories are part of what makes this such a special place to work.

Job Overview 

The Director, Insurance & Risk serves as the enterprise leader responsible for the strategic management and governance of the Company's insurance programs, risk financing activities, captive insurance operations, claims administration, and insurance-related risk transfer strategies. This role protects enterprise assets through effective insurance program oversight, optimization of total cost of risk (TCOR), and alignment of risk financing solutions with the organization's evolving business objectives.  

The Director provides strategic leadership for the Company's captive insurance structure, reinsurance strategy, and opportunities to expand captive utilization. Working closely with Finance, Treasury, Tax, Legal, brokers, actuaries, carriers, and captive service providers, the role drives risk financing innovation, enhances claims outcomes, improves cost efficiency, and strengthens the organization's overall risk management and insurance governance framework.

What You Will Do 

Insurance Program Leadership

• Serve as the enterprise owner of all corporate insurance programs, including Property, General Liability, Workers' Compensation, Automobile Liability, Directors & Officers, Fiduciary, Crime, Cyber, Employment Practices Liability, Travel Accident, Environmental, Aviation, Marine Cargo, and all other specialty insurance coverages.

• Lead all insurance program renewals, including exposure collection, marketing strategy, coverage negotiations, insurer selection, renewal presentations, executive communications, and implementation.

• Ensure policy language, coverage grants, endorsements, limits, retentions, deductibles, and exclusions appropriately protect the organization's assets, operations, and strategic objectives.

• Oversee maintenance of all insurance policies, certificates of insurance, insurer filings, coverage schedules, and insurance governance documentation.

Captive Insurance & Risk Financing

• Assist in strategic oversight and governance of the company’s captive insurance structure.

• Participate in annual captive business planning, feasibility analyses, financial reviews, actuarial assessments, and performance reporting.

• Evaluate opportunities to increase captive participation and expand utilization to additional lines of coverage where economically beneficial.

• Partner with actuaries, captive managers, reinsurers, brokers, and finance leaders to optimize risk retention structures and reduce total cost of risk.

• Evaluate alternative risk financing solutions, deductible structures, self-insured retentions, collateral requirements, and emerging insurance market opportunities.

Claims Management & Loss Control

• Maintain executive ownership of all significant Workers’ Compensation, General Liability, Property, Auto Liability, Cyber, EPL, and other insured and self-insured claims.

• Direct claims management strategy and governance across carriers, third-party administrators, defense counsel, and internal business stakeholders.

• Participate in claim stewardship reviews, reserve reviews, and litigation reviews to ensure appropriate claims handling and financial accuracy.

• Drive claim closure initiatives, recovery opportunities, subrogation efforts, and loss mitigation programs.

• Develop and monitor KPIs related to claim frequency, severity, closure rates, litigation outcomes, reserve development, and total claim cost trends.

• Partner with Safety, Human Resources, Legal, Asset Protection, and Operations teams to identify trends and implement corrective actions designed to reduce loss frequency and severity.

Budget & Financial Management

• Develop, manage, and forecast the enterprise insurance and risk management budget.

• Monitor premiums, retained losses, broker compensation, captive operating expenses, actuarial fees, consulting expenses, legal costs, and third-party service provider expenditures.

• Identify opportunities to improve cost efficiency while maintaining appropriate levels of risk protection and financial security.

• Lead annual total cost of risk (TCOR) analyses and present recommendations to executive leadership.

Broker, Carrier, and External Partner Management

• Relationship management with insurance brokers, carriers, reinsurers, TPAs, captive managers, actuaries, consultants, and other risk management service providers.

• Lead annual stewardship meetings, service performance reviews, and strategic planning sessions with external partners.

• Negotiate coverage enhancements, fee structures, service expectations, and performance standards with insurance market participants.

• Maintain awareness of insurance market conditions, emerging risks, and industry trends to proactively position the company's insurance portfolio.

Enterprise Risk Governance

• Establish and maintain enterprise insurance governance processes to ensure business units appropriately disclose operational, contractual, and strategic changes impacting risk exposures.

• Partner with Legal and Procurement to establish insurance and indemnification standards that support effective contractual risk transfer.

• Support mergers, acquisitions, divestitures, and strategic initiatives through insurance due diligence, coverage assessments, and integration planning.

• Prepare executive-level reports and presentations regarding insurance program performance, claims activity, emerging risks, captive utilization, and TCOR initiatives.

• Foster a risk-aware culture throughout the organization through education, communication, and training.

Leadership & Team Development

• Lead, mentor, and develop a high-performing risk management team.

• Collaborate with cross-functional teams (Operations, Legal, HR, Tax, Legal) to support corporate objectives.

Skills You Will Need

Insurance Program Expertise: Deep knowledge of enterprise-wide insurance program design, underwriting, policy wording, claims management, alternative risk financing, and captive insurance structures. 

Risk Financing & Captive Management: Demonstrated experience leading captive insurance programs, retention analyses, actuarial reviews, reinsurance placements, and risk financing strategies. 

Financial Acumen: Strong understanding of insurance budgeting, retained loss forecasting, captive financial performance, and total cost of risk measurement and optimization. 

Relationship Management: Proven ability to lead strategic relationships with executive leadership, brokers, insurers, reinsurers, regulators, actuaries, and third-party administrators.

Stakeholder Engagement: Builds trusted relationships with business units (e.g., Operations, HR, Legal, Tax, Safety), insurance brokers, strategic service providers, insurance carriers, and other external partners.

Negotiation Skills: Effective in risk-transfer negotiations, with a holistic view of relationships, pricing and services.

Results-oriented leadership – Inspires and drives teams to achieve measurable outcomes, ensuring accountability and alignment with organizational goals.

Process Improvement – Demonstrated ability to identify inefficiencies and drive automation or enhancements in risk/insurance workflows.

Problem Solving & Decision Making – Strong critical thinking skills with the ability to troubleshoot issues and make informed decisions.

Communication – Excellent verbal and written communication skills to effectively convey complex information across teams and to external partners.

Time Management – Ability to prioritize and manage multiple responsibilities and deadlines in a fast-paced environment.

Ethics & Integrity – Unwavering commitment to ethical standards, with a reputation for operating transparently and earning trust across all levels of the organization.

Who You Are

• Bachelor’s degree in Risk Management, Finance, Business Administration, or related field; CRM (Certified Risk Manager) preferred.
• +10 years of risk and insurance experience with a large corporate enterprise, preferred captive management experience.
• Proven track record of leading teams and influencing senior executives.
• Excellent analytical, strategic thinking, and problem-solving skills.
• Strong leadership, communication, and relationship management abilities.
• This role involves performing essential job functions such as communication, collaboration, and use of office and computer systems. Responsibilities include the ability to access and review written and electronic information, and to move within the work environment and interact with workplace materials as needed to carry out job responsibilities.
• Able to work a flexible schedule based on department and company needs, including occasional travel to meet internal partners, insurance carriers, brokers, conferences, etc.

What We Can Offer You

Join a team where work is as rewarding as it is fun! We offer a dynamic, inclusive environment with competitive pay and benefits. Enjoy comprehensive health and wellness coverage and a 401(k) match to invest in your future. Prioritize your well-being with paid time off and eight paid holidays. Grow your career with continuous learning and leadership development. Plus, build community by joining one of our Colleague Resource Groups and make a difference through our volunteer opportunities. 

Some additional benefits we offer include:

• Merchandise discounts
• Performance-based incentives
• Annual merit review
• Employee Assistance Program with mental health counseling and legal/financial advice
• Tuition reimbursement

Access the full menu of benefits offerings here. 

About Us

This is a great time to join Macy’s! Whether you’re helping a customer find the perfect gift, streamlining operations in one of our distribution centers, enhancing our online shopping experience, buying in-style and on-trend merchandise to outfit our customers, or designing a balloon for the Thanksgiving Day Parade, we offer unique opportunities to be part of some of the most memorable moments in people’s lives. 

Join us and help write the next chapter in our story - apply today! 

This job description is not all-inclusive. Macy's, Inc. reserves the right to amend this job description at any time. Macy's, Inc. is an Equal Opportunity Employer, committed to a diverse and inclusive work environment. 

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