Assistant Controller (Hybrid)

Windward Risk; Boca Raton, Northern (FL, KY); Hybrid; USD 85,000 - 115,000; Full time

Benefits offered by this job

Health insurance (employer paid)

401(k) with match

Disability insurance

Paid time off 3 weeks + holidays

Tuition reimbursement

Job summary

Windward Risk is seeking an experienced accounting professional to manage day-to-day accounting activities including GL, Accounts Payable, Commissions and Claims Billing, and to lead the GL Accounting team through month-end close. The role supports financial reporting, audits, budgeting, and internal controls.

The position offers a hybrid schedule (4 days in office, 1 remote after training). During training (up to 6 months), work full-time in office.

Qualifications

• Bachelor’s degree in Accounting required.
• CPA license required.
• 5+ years of progressive accounting experience; public company exposure preferred.
• Budgeting, cost analysis, and cost allocation experience a must.
• Experience leading month-end close and financial reporting.

Responsibilities

• Lead month end close and prepare monthly financial statements/packages.
• Review journal entries, reconciliations, and month-end reports.
• Collaborate with Commissions team to develop, analyze, and reconcile reports.
• Support Accounts Payable and Claims Billing functions as needed.
• Train and mentor junior staff; assist with audits and system improvements.

Skills

Leadership

Budgeting

Cost analysis

Month-end close

Financial reporting

Education

Bachelor’s degree in Accounting

CPA license

Tools

Excel (Advanced)

Job description

Job DetailsJob Location: Corporate Office - Boca Raton, FL 33487Position Type: Full TimeJob Shift: DayJob Category: Accounting*****NO RECRUITERS PLEASE*****

POSITION SUMMARY:

The position will be managing and supporting day to day accounting activities including Accounts Payable, Commissions and Claims Billing functions, as well as managing the GL Accounting team with month end closing activities and producing company’s financial statements. Supporting the Finance Controller with financial reporting, audits, budgeting, cost allocation, and internal controls.

This position offers a hybrid schedule of 4 days in office and 1 day remote following the initial training period. During training (up to 6 months), the position is fully in office 5 days per week.

ESSENTIAL FUNCTIONS:

General Ledger and Financial Reporting

• Lead month end closing and preparation of internal monthly financial statements and packages.
• Review journal entries, balance sheet reconciliations, and reports for month-end and or as needed basis.
• Work closely with Commissions team to develop, analysis, 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 for process and reporting improvements.
• Perform other duties as required and as assigned.

Budgeting & Financial Analysis

• Lead the annual operating budget process in coordination with department heads, including guidance on budget assumptions, timelines, and documentation.
• Maintain detailed department level budgets within the financial system and supporting models.
• Prepare monthly budget to actual variance analyses, identifying key drivers and trends.
• Partner with department leaders to review variances, validate explanations, and support corrective action where needed.
• Ensure budgets align with approved organizational objectives and cost structures.

Cost Allocation & Expense Management

• 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.

Why Windward Risk Managers:

• Windward Risk Managers is proud to be recognized on Fortune's 2026 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

QualificationsREQUIRED EDUCATION AND EXPERIENCE:

• Bachelor’s degree in Accounting
• Certified Public Accountant (CPA) license
• More than five years of progressive accounting experience, preferably in publicly traded companies and multi company environment
• Experience in budgeting, cost analysis, and cost allocation
• Experience leading month close
• Strong understanding of month end close and adherence to meeting deadlines

PREFERRED QUALIFICATIONS:

• Ability to multi task and adapt to changing priorities
• Strong analytical and problem solving skills with attention to detail
• Advanced Excel skills, including complex formulas and financial models
• Solid understanding of general ledger accounting and expense structures
• Ability to clearly communicate financial concepts to non financial audiences
• Proven ability to work collaboratively across departments while maintaining financial discipline
• Highly organized, with the ability to manage multiple priorities and deadlines

Due to current business and operational considerations, we currently hire employees residing in the following states at this time:AL, AR, CA, CT, FL, GA, KY, MO, NC, NV, OH, SC, TN, TX, VA, andWI.

Work Authorization Requirement: This role requires permanent U.S. work authorization and does not offer employer sponsorship now or in the future.

WRM is committed to providing equal employment opportunities to all employees and applicants without regard to race, color, religion, sex, sexual orientation, gender identity or expression, national origin, disability, or veteran status. We take affirmative action to ensure that all employment decisions are based on merit, qualifications, and abilities.

Notice to Third Party Agencies: WRM does not accept unsolicited resumes from third party recruiting firms. Absent a signed Service Agreement by WRM’s Human Resources Department, WRM reserves the right to pursue and hire these candidates without financial obligation to recruiters or agencies.