Assistant Controller

Corporate Office - Boca Raton, FL 33487

Position Type:

Job Shift:

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Experienced Senior Accountants and Accounting Managers with an active CPA license are encouraged to apply. We are seeking professionals with expertise in budget preparation, leadership of month-end close processes, team management, and driving process improvement initiatives.

Windward Risk Managers is seeking an experienced and detail-oriented Assistant Controller (CPA Required) to support the Controller in leading the organization's accounting and financial reporting functions. This highly visible leadership role is responsible for overseeing month-end close. financial reporting, budgeting, cost allocation, financial analysis, and accounting operations while providing guidance and mentorship to the accounting team.

The ideal candidate will have a strong foundation in financial reporting, budgeting, and process improvement, along with a proven ability to manage multiple priorities in a fast-paced environment.

Hybrid

Schedule:

This position offers a hybrid schedule of four days in the office and one day remote following the initial training period. During training (up to six months), the position is fully onsite five days per week.

• Lead month-end closing and preparation of monthly internal financial statements and reporting packages.
• Review journal entries, balance sheet reconciliations, and reports.
• Work closely with the Commissions team to develop, analyze, and reconcile reports and statements.
• Support Accounts Payable and Claims Billing functions as needed.
• Train and mentor junior staff.
• Assist with annual audit preparations.
• Assist with system reviews and process improvements.
• Perform other duties as assigned.

• Lead the annual operating budget process in coordination with department heads.
• Maintain department-level budgets and support models.
• Prepare monthly budget-to-actual variance analyses.
• Partner with department leaders to review variances and support corrective actions.
• Ensure budgets align with organizational objectives and cost structures.

• Develop, document, and maintain cost allocation methodologies across departments, entities, and cost centers.
• Ensure cost allocations are applied consistently, accurately, and in accordance with internal policies.
• Collaborate with Accounting to reconcile allocated costs to the general ledger and resolve discrepancies.
• Assesses allocation methodologies periodically to ensure continued appropriateness and transparency.

• Windward Risk Managers is proud to be recognized on Fortune’s Best Medium Workplaces list, ranking #28 among the Top 100 companies
• 100% employer paid health insurance for employees
• Up to 6% 401(k) match with immediate vesting
• Long-term and short-term disability insurance
• 3 weeks PTO to start + generous paid holidays
• Tuition reimbursement and continuing education support
• Collaborative and growth focused culture

• Bachelor’s degree in accounting
• Active CPA License (Required)
• More than five years of progressive accounting experience, preferably in publicly traded and multi-entity environments
• Experience in budgeting, cost analysis, and cost allocation
• Experience leading month-end close
• Strong understanding of financial reporting and meeting deadlines

• Strong analytical and problem-solving skills
• Advanced Excel skills, including complex formulas and financial models
• Solid understanding of general ledger accounting and expense structures
• Ability to communicate financial…