Director of Client Accounting

WESTWARD360 ASSOCIATION MANAGEMENT LLC•Chicago, IL

1d•$80,000 - $100,000•Hybrid

About The Position

Westward360 is seeking a transformative leader to join their organization as Director of Client Accounting. This role will lead and strengthen the accounting operations supporting a growing portfolio of condominium and homeowners associations. The Director of Client Accounting will oversee a team of accounting professionals and be responsible for delivering accurate, timely, and high-quality financial management across a large association client base. The ideal candidate will bring strong property management accounting expertise, a hands-on leadership style, and the ability to build trust with board members, internal partners, and clients. Success in this role requires a sharp understanding of accounting operations, team development, process improvement, and the ability to drive consistency and efficiency in a fast-paced, high-volume environment.

Requirements

Bachelor’s degree in Accounting, Finance, or a related field.
5+ years of progressive accounting experience, including leadership or management responsibilities.
Experience in real estate or property management is strongly preferred.
Strong knowledge of client relationships, budgeting, and financial reporting.
Proficiency in client accounting systems (Vantaca, Appfolio, Strongroom, Quickbooks preferred) and Excel/Google Sheets.
Excellent leadership, organizational, and communication skills.
Demonstrated experience leading large teams and high-volume client portfolios
High attention to detail with the ability to manage multiple priorities in a fast-paced environment.

Responsibilities

Lead, mentor, and develop a global workforce of 100+ offshore and onshore accounting professionals, creating a cohesive, accountable, and high-performing team.
Own the systems and processes supporting the full accounting lifecycle for 1,000+ community associations across all markets.
Evaluate and optimize departmental structure, leadership layers, and workflows to maximize efficiency, clarity, and scalability.
Engineer scalable operating models capable of supporting bulk acquisition events while maintaining service excellence for existing clients.
Build a culture of professional development, accountability, and operational excellence that positions Westward360 as an employer of choice in the industry.
Oversee onboarding systems and processes, including bank account setup, financial data integration into Vantaca, and management of starter and closeout balances from prior management companies.
Oversee contractual financial service deliverables, including review and approval of monthly financial statements and annual operating budgets.
Lead monthly pre-close and close processes, ensuring accuracy, timeliness, and compliance with internal controls.
Partner with Accounts Payable to ensure proper authorization, coding, and timely payment of one-time and recurring disbursements.
Supervise account analysis and reconciliations to ensure accurate, timely, and compliant financial reporting.
Lead the annual operating budget preparation process, ensuring alignment with governing documents, reserve funding requirements, and Board priorities.
Manage federal and state tax preparation processes in coordination with external tax providers.
Oversee the daily flow of accounting-related inquiries, ensuring timely responses, issue resolution, and a high standard of client service.
Ensure accurate GL coding, account closures, fund disbursement, and delivery of final financial statements during management transitions.
Design, maintain, and continuously improve a robust system of internal controls.
Provide ongoing training and development for accounting staff responsible for day-to-day financial operations.
Establish clear processes for identifying, reporting, and resolving discrepancies in partnership with Community Managers.
Proactively manage workloads and staffing assignments to ensure consistent coverage.
Own banking relationships and oversee all financial system integrations to ensure reliability, compliance, and seamless end-to-end service delivery.
Serve as the final executive point of escalation for complex or critical accounting issues.
Engage directly with Boards and Community Managers to resolve issues related to owner ledgers, payments, balance sheets, income statements, and budgets.
Champion transparency, responsiveness, and trust through clear communication and decisive resolution.