Assistant Controller

Windward Risk Managers • Boca Raton, FL

23d • Hybrid

About The Position

Windward Risk Managers is seeking an experienced, detail-oriented Assistant Controller to support the Controller in leading the organization’s accounting and financial reporting functions. This leadership role oversees month-end close, financial reporting, budgeting, cost allocation, financial analysis, and accounting operations, while guiding and mentoring the accounting team. The position calls for strong financial reporting, budgeting, and process-improvement capabilities and the ability to manage multiple priorities in a fast-paced environment.

The position is based at the corporate office in Boca Raton, Florida, with a hybrid schedule of four office days and one remote day after the initial training period. Training may last up to six months, during which the role is fully onsite five days per week.

Requirements

• Bachelor’s degree in accounting.
• Active CPA license.
• More than five years of progressive accounting experience.
• Experience in budgeting, cost analysis, and cost allocation.
• Experience leading month-end close.
• Strong understanding of financial reporting and meeting deadlines.
• Permanent U.S. work authorization; employer sponsorship is not offered now or in the future.
• Must reside in one of the states currently eligible for hiring: AL, AR, CA, CT, FL, GA, KY, MO, NC, NV, OH, SC, TN, TX, VA, or WI.

Nice To Haves

• Accounting experience in publicly traded and multi-entity environments.
• 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 concepts to non-financial audiences.
• Proven ability to collaborate across departments.
• Highly organized, with the ability to manage multiple priorities.

Responsibilities

• Lead month-end closing and prepare monthly internal financial statements and reporting packages.
• Review journal entries, balance sheet reconciliations, and reports.
• Work 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.
• 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 and accurately in accordance with internal policies.
• Collaborate with Accounting to reconcile allocated costs to the general ledger and resolve discrepancies.
• Periodically assess allocation methodologies for continued appropriateness and transparency.
• Perform other duties as assigned.

Benefits

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

What This Job Offers

• Job Type: Full-time
• Career Level: Senior