Director, Insurance Captive & Accounting

Director, Insurance Captive & Accounting

The Director, Insurance Captive & Accounting sits within the Risk Management team and is the owner of the organization's captive insurance program and broader risk financing strategy. This role manages captive operations, program performance reporting, capital planning, and new program development. This role works closely with risk managers and the captive Board of Directors to execute the strategy of the captive. The Director carries a dotted-line relationship with Accounting and Finance, coordinating on premium allocations, deposit accounting, and MIP/risk fee forecasting, but is not responsible for owning the enterprise accounting function. The role also partners closely with Treasury, Actuarial, Legal, Payroll, and GMS to execute risk financing programs. This position is a key advisor to senior leadership on captive performance, capital allocation, new program opportunities, and risk financing strategy in support of the company's enterprise risk management objectives.

Key Responsibilities:

Captive Insurance & Risk Finance Leadership

Direct financial management and operational oversight of the company's captive insurance programs.

Own loss run validation, actuarial reporting review, and financial reconciliations to ensure accuracy and consistency across reporting sources.

Establish and document internal controls and governance frameworks for captive and risk finance workflows.

Facilitate reinsurance premium and loss payment tracking and monitor compliance with captive regulatory and program obligations.

Oversee the captive auditor relationship, ensuring timely policy issuance, and manage relationships with actuaries, third-party administrators, and other strategic vendors.

Capital Management & Financial Strategy

Partner with the Treasurer to develop recommendations on captive capitalization, funding requirements, and distribution strategy.

Coordinate with Treasury and Finance on implementation and monitoring of investment policy for captive assets.

Evaluate regulatory capital requirements against downside risk exposure and business objectives.

Program Performance & Executive Reporting

Develop and deliver reporting on captive and risk financing program performance, including value creation generated beyond the captive.

Design and maintain underwriting performance summaries, forecasting models, and performance dashboards.

Present program results and strategic recommendations to executive leadership.

Perform NPV, volatility, and sensitivity analysis to evaluate new program and risk transfer opportunities.

Build the governance frameworks, controls, and operating procedures required to implement newly approved programs.

Accounting Coordination (Dotted Line)

Maintain a consolidated risk management view of accounting activity and budgets, in coordination with Finance and Accounting.

Assist with premium allocation methodologies across business units and/or the captive.

Own deposit accounting activities when captive solutions are not appropriate and provide oversight of program revenue/expense items sitting at the company rather than within the captive.

MIP & Workers' Compensation

Partner with the property management business to develop risk fee projections and forecasting assumptions.

Lead Workers' Compensation audit reviews and coordinate audit activities with Payroll (scope pending finalization per current working memo).

Basic Knowledge & Qualifications:

Bachelor's degree in Risk Management, Finance, Accounting, Business Administration, or related field.

810 years of progressive experience in captive insurance, risk finance, or related insurance disciplines.

Experience independently managing a complex insurance program, captive entity, or alternative risk financing structure.

Demonstrated success developing executive-level reporting, forecasts, and financial analyses.

Excellent communication and negotiation abilities.

Knowledge of current market trends and regulatory requirements.

Abilities to create and manage stakeholder relationships.

Deep understanding of captive insurance operations, reinsurance structures, and risk financing strategy.

Strong financial modeling, forecasting, and business analysis capabilities, including NPV and volatility analysis.

Working knowledge of insurance/risk finance accounting principles sufficient to partner effectively with Finance and Accounting.

Knowledge of internal controls, regulatory compliance, and audit processes for captive entities.

Ability to operate autonomously and communicate complex insurance and financial concepts to executive audiences.

Proven ability to lead cross-functional initiatives and influence stakeholders across Treasury, Finance, Actuarial, Legal, and Payroll.

Specialized Skills:

ARM, CPCU, CIRA, CPA, or other relevant professional designations.

Experience with captive insurance company operations and governance.

Background in real estate, asset management, or other complex multi-entity organizations.

Experience working directly with insurance regulators, auditors, and actuaries.

Travel / Physical Demands:

Team members work in an office or remote work environment. No special physical demands are required.

Rare or occasional travel may be required to attend business meetings, training programs, or other situations necessary for the accomplishment of some or all of the daily responsibilities of this position.

#LI-DNI

Additional Compensation:

Many factors go into determining employee pay within the posted range including business requirements, prior experience, current skills and geographical location.

• Corporate Positions: In addition to the base salary, this role may be eligible to participate in a quarterly or annual bonus program based on individual and company performance.
• Onsite Property Positions: In addition to the base salary, this role may be eligible to participate in weekly, monthly, and/or quarterly bonus programs.

Robust Benefits Offered*:

• Competitive Medical, Dental, Vision, and Disability & Life insurance benefits. Low (free basic) employee Medical costs for employee-only coverage; costs discounted after 3 and 5 years of service.
• Generous Paid Time off. All new hires start with 15 days of vacation, 4 personal days, 10 sick days, and 11 paid holidays. Plus your birthday off after 1 year of service! Additional vacation accrued with tenure.
• For onsite team members, onsite housing discount at Greystar-managed communities are available subject to discount and unit availability.
• 6-Week Paid Sabbatical after 10 years of service (and every 5 years thereafter).
• 401(k) with Company Match up to 6% of pay after 6 months of service.
• Paid Parental Leave and lifetime Fertility Benefit reimbursement up to $10,000 (includes adoption or surrogacy).
• Employee Assistance Program.
• Critical Illness, Accident, Hospital Indemnity, Pet Insurance and Legal Plans.
• Charitable giving program and benefits.

*Benefits offered for full-time employees. For Union and Prevailing Wage roles, compensation and benefits may vary from the listed information above due to Collective Bargaining Agreements and/or local governing authority.

Greystar will consider for employment qualified applicants with arrest and conviction records.

Greystar is an equal opportunity employer and does not discriminate in employment on the basis of race, color, religion, sex (including pregnancy, sexual orientation, and gender identity), national origin, age, disability, genetic information, military or veteran status, or any other characteristic protected by applicable law.

Important Notice: Greystar will never request your banking details or other sensitive personal information during the interview process. Greystar does not conduct any interviews via text or messaging, and all communication will come from official Greystar email addresses (@greystar.com). If you receive suspicious requests, please report them immediately to View email address on click.appcast.io.