Regional Community Leader & Strategy Director

associacareers; Chicago (IL); On-site; USD 120,000 - 180,000; Full time

Job summary

associacareers seeks a Community Director to provide strategic leadership across multiple communities, mentor managers, and partner with the VP of Operations to drive client satisfaction and financial performance. The role focuses on developing talent, overseeing operations, and strengthening client relationships while promoting accountability and continuous improvement across branches in the Chicago area.

You'll monitor budgets, oversee transitions, and align workforce with business objectives,

Qualifications

• 7+ years of community association, property management, or related operational leadership experience.
• 3+ years of leadership, supervisory, or management experience.
• Experience working directly with Boards of Directors and community stakeholders.
• Experience managing escalations, client relationships, and operational performance.

Responsibilities

• Provide direct leadership, coaching, and mentorship to Community Managers and Assistant Directors.
• Conduct regular one-on-one meetings with direct reports.
• Partner with managers to establish professional development goals.
• Support employee engagement and retention initiatives.
• Assist with performance management conversations and employee development planning.
• Provide training and onboarding support for new managers and team members.
• Foster a culture of accountability, collaboration, and continuous improvement.
• Identify future leaders and support succession planning efforts.
• Build and maintain strong relationships with Board Members and key client stakeholders.
• Partner with managers to improve client satisfaction and community performance.
• Participate in client retention meetings and strategic client reviews.
• Address high-level client concerns and elevate issues as appropriate.
• Assist with resolution of complex customer service issues and board concerns.
• Support managers in navigating difficult board relationships and challenging situations.
• Monitor client satisfaction trends and proactively identify retention risks.
• Monitor branch operations and community performance metrics.
• Review community deliverables and ensure service expectations are met.
• Assist with oversight of community transitions, including onboarding and offboarding of communities.
• Support implementation of operational initiatives and process improvements.
• Review workloads and staffing needs to ensure appropriate resource allocation.
• Partner with leadership to maintain consistency across management practices.
• Serve as a resource for managers on community operations, inspections, projects, and governance matters.
• Review community financial statements and budgets with managers.
• Partner with accounting teams to address financial escalations and concerns.
• Monitor budget performance and identify areas of risk.
• Assist managers and boards with budget planning and financial discussions.
• Review reserve funding strategies and major project planning.
• Support financial accountability and stewardship across managed communities.
• Partner with Human Resources and leadership on recruitment efforts.
• Participate in interviewing and candidate selection processes.
• Assist with onboarding and training initiatives.
• Support the development of Community Manager training programs.
• Identify skill gaps and recommend development opportunities.
• Encourage professional education and industry certifications.
• Participate in branch leadership meetings and planning sessions.
• Support business development efforts, including client presentations and relationship-building activities.
• Assist with strategic initiatives designed to improve operational efficiency, employee engagement, and client retention.
• Analyze trends, performance metrics, and operational data to make informed recommendations.
• Contribute to branch growth and organizational success.
• Strong leadership presence and coaching ability
• Ability to motivate, develop, and hold employees accountable
• Excellent interpersonal and relationship-building skills
• Strong conflict resolution and problem-solving abilities
• Strong understanding of community association management operations
• Ability to evaluate business performance and operational effectiveness
• Knowledge of strategic planning and organizational development
• Ability to prioritize competing responsibilities
• Knowledge of financial statements, budgets, and reserve planning
• Understanding of financial analysis and reporting
• Ability to communicate financial information to non-financial audiences
• Exceptional verbal and written communication abilities
• Professional presentation and public speaking skills
• Ability to communicate effectively with boards, homeowners, employees, vendors, and executive leadership
• Proficiency in Microsoft Outlook, Excel, Word, PowerPoint, Teams, and SharePoint
• Ability to utilize reporting tools and dashboards to support decision-making
• Strong organizational and documentation skills

Skills

Leadership

Business Acumen

Financial Analysis

Communication

Technology Proficiency

Education

Bachelor's Degree in Business or related field

CMCA designation

AMS designation

PCAM designation

Tools

Microsoft Outlook

Excel

Word

PowerPoint

Teams

SharePoint

Job description

associacareers seeks a Community Director to provide strategic leadership across multiple communities, mentor managers, and partner with the VP of Operations to drive client satisfaction and financial performance. The role focuses on developing talent, overseeing operations, and strengthening client relationships while promoting accountability and continuous improvement across branches in the Chicago area.

You'll monitor budgets, oversee transitions, and align workforce with business objectives,