Senior Vice President, Community Management at WESTWARD360 ASSOCIATION MANAGEMENT LLC – Chicago, Illinois

Westward360 is looking to add a Senior Vice President, Community Management to our executive leadership team. This is a high-impact opportunity for a strategic, results-driven leader to oversee and evolve our community management division across all markets.

This role is responsible for driving predictable revenue, strengthening product superiority, and elevating customer retention by continuously optimizing our services, talent, and operational model. If you are energized by scale, accountability, and building best-in-class community management operations — we want to hear from you.

Westward360 is a leader in the Community Management industry, with locations across the map. We service condo, townhome, and homeowner associations, and provide rental management services to multi-family, single-unit, and co-op properties.

What we offer:

• Base salary of $120,000–$140,000, plus bonus eligibility
• In-office presence expected 4 days per week in the Chicagoland area
• National travel up to once per month; international travel annually
• Medical, Dental, and Vision insurance
• Monthly cell phone stipend
• Unlimited PTO
• 401(k) with company match up to 4%
• Long- and short-term disability at no cost to employee
• Executive-level influence within a fast-growing organization
• Opportunity to shape strategy, operations, and client experience at scale

What you’ll do:

The Senior Vice President, Community Management is accountable for the overall success, scalability, and performance of Westward360’s community management division. This role partners closely with Executive Leadership to execute company vision, drive revenue growth, improve operational efficiency, and ensure an exceptional client experience across all markets.

You will lead Vice Presidents and General Managers of Community Association Management (CAM), ensuring alignment, accountability, and consistent execution of divisional initiatives.

Division Leadership & Strategy

• Serve as executive leader for the Community Management division, reporting directly to the Management Company President (MCP).
• Provide ongoing insight, recommendations, and performance updates to the MCP and Executive Leadership Team.
• Implement and reinforce company vision, culture, and values across the CAM division.
• Identify opportunities to enhance, retool, and scale community management products and services to meet evolving market and client needs.

Predictable Revenue & Growth

• Drive predictable, recurring revenue through optimized management contracts and value-added services.
• Ensure contractual structures balance client expectations, staff workload, and company profitability.
• Partner with Sales & Marketing to develop new programs and offerings that expand market share among both new and existing clients.
• Support development of differentiated services that create win-win-win outcomes for clients, employees, and the organization.

Product Superiority & Operational Excellence

• Continuously assess and enhance service delivery models, staffing structures, and operational workflows.
• Ensure community management services are accurate, efficient, easy to engage with, and clearly differentiated in the marketplace.
• Oversee CAM operational performance, efficiency, and consistency across all regions.
• Monitor and adjust CAM loads to ensure profitability, balanced workloads, and service quality, in collaboration with Finance, Operations, and regional leadership.
• Establish standardized policies, reporting, and guidance to support load utilization and strategic staffing decisions.

Customer Retention & Client Experience

• Partner closely with the Vice President of Client Success to strengthen client retention and elevate the customer experience.
• Use NPS data, client feedback, and performance metrics to improve service delivery and long-term loyalty.
• Work with General Managers to develop and execute client retention strategies and escalation management plans.
• Serve as the final point of escalation for Vice Presidents and General Managers of CAM, ensuring escalation pathways are defined, followed, and resolved effectively.
• Attend board meetings as needed to support client relationships and strategic outcomes.

Financial & Cross-Functional Leadership

• Review budgets, financial projections, and performance metrics; approve additional expenses and one-off project requests as appropriate.
• Collaborate with the VP of CAM Accounting to ensure quality, accuracy, and consistency of community financials.
• Assist the MCP and CFO with department budgeting, forecasting, and long-term financial planning.
• Support Executive Leadership in identifying and developing new revenue streams.

People Leadership & Collaboration

• Directly lead and develop Vice Presidents and General Managers of CAM.
• Task leaders with developing and executing strategic initiatives and ensure follow-through across divisions.
• Attend and lead weekly and ongoing CAM divisional meetings.
• Identify areas of development within the CAM division and implement policies, procedures, and training to address performance gaps.
• Promote cross-training, best-practice sharing, and collaboration across departments.
• Encourage a customer-centric, accountable, and performance-driven culture.

What you’ll need:

• Bachelor’s degree required.
• Proven executive or senior leadership experience with demonstrated success in operational leadership and growth.
• Experience leading multi-layered teams and cross-functional initiatives.
• Strong financial acumen, including budgeting, forecasting, and revenue growth strategies.
• Creative, solutions-oriented mindset with an entrepreneurial drive.
• High comfort level with technology platforms and operational software.
• Excellent communication, negotiation, presentation, and relationship-building skills.
• Ability to work independently while collaborating effectively with executive peers.
• Alignment with Westward360’s mission, values, and commitment to service excellence.

Preferred Qualifications:

• Experience in multi-state or multi-market operations.
• Background in system implementation, user administration, or workflow design.
• CAI designations (CMCA, AMS, PCAM) strongly preferred.
• Experience in a rapidly scaling or acquisitive organization.

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.