Senior Associate, Finance & Accounting Outsourcing - Captive Insurance
Cherry Bekaert · Richmond, Virginia · Posted Jul 3, 2026
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Cherry Bekaert, a leading full-service accounting and advisory firm, is on the lookout for an Experienced Captive Manager and Accountant to become an integral part of our Finance & Accounting Outsourcing (FAO) team, specializing in the Captive Insurance industry. This role is pivotal in ensuring the delivery of high-quality outsourced accounting and regulatory filing services for various client engagements. As an Experienced Senior Accountant, you will take charge of daily accounting operations, comprehensive reporting, and captives' monthly, quarterly, and annual close activities.
Join us and make a difference by supporting captive insurance entities with all components of operational accounting, including:
- General ledger management
- Accounts payable
- Accounts receivable
- Payroll coordination
- Account reconciliations
You will play a vital role in preparing monthly and quarterly financial packages (including Balance Sheets and Income Statements), managing regulatory reporting, and generating month-end and year-end financial statements. The position provides exciting opportunities to collaborate closely with clients, fellow captive managers, actuaries, and external auditors, all while mentoring junior staff and driving process improvements.
Key Responsibilities:
- Conduct day-to-day and month-end accounting tasks, including journal entries in key areas such as:
- Premium revenue recognition
- Loss reserves and IBNR accruals
- Prepaid expenses and accrued liabilities
- Cash and investment accounting
- Perform complex balance sheet reconciliations and address discrepancies swiftly.
- Assist in monthly, quarterly, and year-end close processes for captive insurance clients.
- Prepare and review comprehensive financial reporting packages for management and board members.
- Gain and maintain a thorough understanding of each assigned client's operations and accounting systems.
- Contribute to statutory and GAAP-compliant financial reporting when applicable.
- Support regulatory filings and compliance for captive insurance entities.
- Collaborate with actuaries and TPAs on loss reserve analyses and claims data reconciliation.
- Facilitate audits by preparing schedules and documentation for external auditors and tax advisors.
- Help prepare and review annual 1099 filings.
- Propose and implement accounting controls, policies, and process enhancements.
- Communicate proactively with clients about accounting matters, deliverables, and timelines.
Supervisory Responsibilities:
- Oversee and review the work of Staff Accountants, ensuring quality and correctness.
- Mentor and coach staff, supporting their professional development.
- Distribute projects among team members and manage deadlines effectively.
- Ensure high standards for deliverables in a dynamic, client-focused environment.
Qualifications:
- Bachelor's degree in Accounting or related field.
- 3+ years of relevant accounting experience, ideally within the insurance or captive insurance sectors.
- Experience in managing multiple client engagements in a public accounting or outsourced environment is preferred.
- Proficient in automated accounting systems and spreadsheets; familiarity with QuickBooks, Sage, or similar systems is a plus.
- Advanced skills in Microsoft Excel are essential.
- Strong knowledge of GAAP and statutory accounting principles (SAP).
- Understanding of captive insurance operations, including:
- Premium and underwriting income
- Loss reserves and claims accounting
- Reinsurance arrangements
- Investment accounting
- Capital and equity management
- Excellent written and verbal communication skills.
- Detail-oriented with impressive analytical and problem-solving skills.
- Ability to juggle multiple engagements and deadlines.
- Strong organizational and time-management capabilities.
- Ability to work independently and collaboratively.
- Adaptable in a fast-paced, client-centered environment.
- Demonstrated professionalism and strong ethics.
- CPA license preferred, but not mandatory.
What You Can Expect from Us:
- We foster an inclusive culture centered around integrity, collaboration, and mutual respect.
- An innovative work environment that challenges and excites you.
- A supportive team atmosphere focused on your professional development.
- Competitive compensation and a comprehensive benefits package prioritizing your well-being.
- Flexible work arrangements that allow you to maintain a healthy work-life balance.
- Opportunities to connect with diverse professionals from various backgrounds.
Cherry Bekaert values its employees, offering competitive compensation that reflects our team’s contributions. The salary range for this position is between $103,000 and $134,000. Individual salaries are determined by a variety of factors, including experience, education, and geographical location.
About Cherry Bekaert:
Cherry Bekaert is one of the largest assurance, tax, and advisory firms in the U.S., providing services across industrie…