Director of Finance / Controller

Our Mission

Windward is a coeducational, independent day school dedicated to providing a proven instructional program for children with language-based learning disabilities. The multisensory curriculum is designed for students of average-to-superior intelligence who can benefit from the unique educational experience provided. Through direct instruction in small class settings, a trained staff assists students to improve their language skills. Academic success, combined with opportunities for social and emotional growth within an intentionally diverse and inclusive setting, enables students to understand their learning differences, build confidence, and develop self-advocacy skills. Windward is committed to helping students achieve their full potential in preparation for a successful return to a mainstream educational environment. To meet these goals, the School provides ongoing training to its faculty based on the most current research and shares its expertise with the parent body, other educators, and the broader community.

Our Vision

A world where every child with a language-based learning disability is empowered to achieve unlimited success.

Overview

The Director of Finance / Controller is responsible for the overall integrity, accuracy, timeliness, and effectiveness of The Windward School’s accounting and financial operations. The position provides day-to-day leadership over the accounting function and ensures that financial processes are standardized, well controlled, documented, and completed on a timely basis.

This role serves as the principal tactical financial leader supporting the organization’s transition from historical reporting toward a more timely, process-driven financial environment. The Director of Finance / Controller works closely with FP&A, Operations, Payroll & Benefits, Accounts Receivable, Accounts Payable, and campus leadership to provide accurate financial information and strengthen accountability throughout the School.

The position is expected to execute disciplined financial processes that support the goal of completing financial statements and meaningful financial analysis. 

The position is full time on site.

Direct and Functional Oversight

The Director of Finance / Controller provides leadership and oversight for accounting operations, including coordination with:

• Senior Accountant
• Mid-Level Accountants
• Payroll & Benefits Manager
• Accounts Receivable personnel
• Accounts Payable and purchasing functions
• Campus financial operations

Primary Responsibilities

Accounting and Financial Reporting

• Direct the monthly, quarterly, and annual accounting close.
• Ensure financial statements are accurate, complete, and delivered on a timely basis.
• Establish a target of producing month-end financial statements and supporting analysis within approximately 10 business days. 

• Review general ledger activity, account reconciliations, accruals, prepaid expenses, fixed assets, deferred revenue, and other significant accounts.
• Maintain the integrity of the chart of accounts and financial reporting structure.
• Review financial results for unusual transactions, trends, errors, and inconsistencies.
• Ensure appropriate supporting documentation exists for material accounting transactions.
• Coordinate preparation of financial information required by senior management and FP&A.

Financial Controls and Standard Operating Procedures

• Develop, document, implement, and maintain Standard Operating Procedures for major finance and accounting processes.
• Establish appropriate segregation of duties and review controls.
• Maintain effective controls over receipts, disbursements, payroll, purchasing, and journal entries.
• Develop accounting checklists and recurring close procedures to improve accuracy and accountability.
• Identify areas of financial risk and recommend corrective action.
• Ensure financial processes are consistently followed across campuses and departments.

Accounts Payable and Purchasing

• Provide oversight of purchasing, invoice processing, and vendor-payment procedures.
• Coordinate with FP&A regarding purchase orders and budget availability.
• Strengthen the purchase-order and invoice-matching process. 

• Ensure invoices are properly approved, coded, supported, and paid on schedule.
• Monitor outstanding liabilities and vendor issues.
• Establish processes that create greater financial responsibility and clarity for operating departments.

Accounts Receivable and Billing Oversight

• Provide oversight of Accounts Receivable operations and related financial controls.
• Support improvements in billing and receivable processes.
• Monitor accounts receivable aging and collection performance.
• Work with responsible staff to reduce past-due balances and Days Sales Outstanding.
• Oversee the financial aspects of payment plans and collection activity.
• Review the effectiveness of systems and service providers supporting billing and receivables, including Veracross and Blackbaud-related processes where applicable.
• Evaluate opportunities to improve or bring selected financial processes in-house when economically and operationally appropriate.

Payroll and Benefits Oversight

• Provide financial oversight of payroll operations while the Payroll & Benefits Manager maintains primary responsibility for payroll execution.
• Ensure payroll costs reconcile to the general ledger.
• Review significant payroll adjustments, accruals, and unusual transactions.
• Ensure adequate controls, checklists, approvals, and segregation of duties exist for each payroll. 

• Coordinate with the Payroll & Benefits Manager regarding compliance matters and financial reporting.

Coordination With FP&A

• Provide FP&A with accurate and timely historical financial information.
• Coordinate accounting results with budgeting and forecasting activities.
• Support management with timely information that allows problems to be identified and corrected quickly.
• Ensure financial reporting provides a reliable foundation for forecasts and strategic analysis.

Campus and Operational Support

• Develop consistent financial processes across the School’s campuses and operating departments.
• Monitor adherence to purchasing, budgeting, and approval policies.
• Conduct periodic financial reviews with appropriate operating leaders.
• Help management identify opportunities to reduce unnecessary costs and improve operating efficiency.

Audit, Tax, and Compliance

• Coordinate the annual financial statement audit.
• Prepare schedules and supporting documentation requested by external auditors.
• Coordinate preparation of financial information required for Form 990 and other applicable tax and regulatory filings.
• Maintain appropriate accounting records in accordance with generally accepted accounting principles.
• Monitor compliance with applicable nonprofit accounting and financial reporting requirements. 

• Assist management with responses to audit findings and recommendations.

Staff Leadership and Development

• Supervise, coach, and develop members of the accounting team responsible for accounts payable, accounts receivable, payroll, and other accounting functions across the school 
• Establish clear responsibilities and performance expectations.
• Develop cross-training and rotational training opportunities for finance staff.
• Build a flexible financial team capable of providing backup coverage for critical accounting functions.
• Encourage upward progression and professional development within the finance organization.
• Evaluate work processes and recommend appropriate staffing and responsibility changes.
• Promote a culture of accountability, accuracy, responsiveness, and continuous improvement.

Qualifications

Required

• Bachelor’s degree in Accounting, Finance, Business Administration, or a related field.
• Significant progressive accounting experience, including responsibility for financial reporting and general ledger operations.
• Prior management or supervisory experience.
• Strong understanding of GAAP and internal accounting controls.
• Demonstrated experience managing month-end and year-end closing processes.
• Strong analytical and problem-solving skills 

• Ability to develop and document accounting procedures.
• Strong Excel and financial systems capabilities.
• Ability to communicate financial information effectively to both financial and non-financial managers.

Preferred

• CPA, CMA, MBA, or other advanced financial credentials.
• Experience in an independent school, nonprofit organization, educational institution, or similarly complex organization.
• Experience with fund accounting or nonprofit financial reporting.
• Experience with Veracross, Blackbaud, or comparable school and financial management systems.
• Experience implementing or improving purchase-order, billing, accounts receivable, and financial reporting processes.

Leadership Profile

The successful Director of Finance / Controller will be a hands-on financial leader who combines strong technical accounting skills with a process-improvement mindset. The individual should be comfortable moving between detailed accounting issues and organization-wide financial matters while creating a more disciplined, timely, and accountable finance organization.