Director of Client Accounting in Chicago, Illinois at WESTWARD360 ASSOCIATION MANAGEMENT LLC

Westward360 is on a mission to be the envy of the property management industry—and the employer of choice for top-tier accounting talent. We are seeking a transformative leader to join our organization as Director of Client Accounting to lead and strengthen the accounting operations supporting our growing portfolio of condominium and homeowners associations.

This leadership role oversees a team of accounting professionals and is responsible for delivering accurate, timely, and high-quality financial management across a large association client base. The ideal candidate brings 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.

What we offer:

• Compensation range of $80,000 - $100,000
• Hybrid flexibility
• Medical/Dental/Vision insurance
• Front loaded PTO plus additional personal time
• 401k - Company match up to 4%
• Long and short term disability at no cost to employee
• Career advancement opportunity

What you’ll do:

Strategic Leadership & Organizational Design

• 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.
• Onboarding & Transitions
  • 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.
• Active Community Accounting
  • 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.
• Offboarding & Account Closure
  • Ensure accurate GL coding, account closures, fund disbursement, and delivery of final financial statements during management transitions.

Internal Controls & Quality Assurance

• 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.

Client Satisfaction & Executive Escalation

• 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.

What Success Looks Like:

Success in this role is defined by transforming Client Accounting into a scalable strategic asset that supports Westward360’s aggressive growth strategy.

• A Strategic Advantage: Accounting operations are streamlined, scalable, and differentiated—serving as a selling point and driver of client retention.
• Unshakeable Trust: Boards and Community Managers experience a new standard of accuracy, transparency, and reliability.
• Growth-Ready Infrastructure: Rapid portfolio expansion becomes normalized, supported by disciplined processes, strong controls, and confident leadership.
• At Westward360, financial excellence isn’t just operational—it’s foundational. If you’re ready to build something exceptional at scale, we’d love to talk.

What you’ll need:

• 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.

About Westward360:

Westward360 is dedicated to providing exceptional community management, rental management and brokerage services. Serving multiple markets throughout the United States, we have the systems, strategies, and expertise to meet the specialized needs of even the most demanding client. With more than 50,000 homes under management, we’re your all-in-one real estate solution.

*Disability Notice: Disclosure is divulging or giving out personal information about a disability. It is important for the employee to provide information about the nature of the disability, the limitations involved, and how the disability affects the ability to learn and /or perform the job effectively. The employer has a right to know if a disability is involved when an employee asks for accommodations. Deciding if, when, and how to share disability-related information with a prospective or current employer can be overwhelming but we ask to please request a required accommodation prior to your first date of work. *Please note, a doctor's note may be requested by Human Resources, depending on the accommodation being requested, on a case-by-case basis.