Director of Property Management

Director of Property Management Milestone Realty Aspinwall, PA Job Details Full-time $67,500 - $80,000 a year 1 day ago Benefits Relocation assistance Health insurance Dental insurance Paid time off 401(k) matching Opportunities for advancement Flexible schedule Life insurance Retirement plan Qualifications Operations management Real Estate License Team development Hiring Property management Senior leadership

Full Job Description Director of Property Management Milestone Realty Pittsburgh, PA Salary:

$67,500-$80,000 annually (based on experience)

Benefits:

Medical, PTO, Retirement Plan, Performance Bonuses, Advancement Opportunities Employment Type:

Full-Time Why Work Here? Milestone Realty is a rapidly growing Pittsburgh-based real estate brokerage and property management company specializing in scattered-site residential rental housing throughout the Pittsburgh region. As our portfolio continues to expand, we are seeking an experienced and highly organized Director of Property Management to lead and scale our property management operations. This is a senior leadership position responsible for overseeing the operational performance of the management portfolio, supervising property management staff, improving systems and accountability, and ensuring exceptional service to both owners and tenants. The ideal candidate is a strong communicator, highly organized, operationally minded, and capable of managing multiple moving parts in a fast-paced environment while helping build scalable systems for continued growth. This role is designed to remove day-to-day operational burden from company ownership and executive leadership while helping elevate the structure and professionalism of the department as we continue to expand. Position Overview The Director of Property Management will oversee the daily operations and performance of the company's residential property management portfolio including: Property management staff oversight Owner and tenant relations Delinquency and collections oversight Turnover coordination and operational workflow Leasing and occupancy performance Maintenance coordination with the maintenance department Inspection oversight and compliance Process improvement and departmental accountability Portfolio financial performance and operational reporting The Director of Property Management will work closely with company ownership, maintenance leadership, leasing personnel, accounting staff, and administrative teams to ensure efficient and professional operations across the portfolio. This is primarily an operations and leadership role rather than a field-based leasing or maintenance position. Key ResponsibilitiesDepartment Leadership & Staff Oversight Lead and supervise the property management department Establish accountability, expectations, and operational procedures Recruit, onboard, train, and develop property management staff Conduct regular team meetings and performance reviews Create systems to improve efficiency, communication, and scalability Assist ownership in building long-term departmental structure Portfolio Operations Oversee day-to-day management of residential rental portfolio Ensure properties are professionally managed and operating efficiently Monitor occupancy levels, lease renewals, delinquency, and tenant retention Review operational issues and implement solutions proactively Ensure timely handling of tenant concerns and escalations Oversee move-ins, move-outs, turnovers, inspections, and lease compliance processes Owner Communication & Client Relations Serve as a high-level point of contact for owner-clients Communicate operational updates, larger repair recommendations, and portfolio concerns Help strengthen owner relationships through professionalism, responsiveness, and transparency Assist in onboarding new management clients and portfolio transitions Review owner statements, reserve balances, and operational concerns when necessary Maintenance & Turnover Coordination Coordinate closely with the Maintenance Director and maintenance department Ensure turnovers are progressing efficiently and within timeline expectations Review larger maintenance approvals and project scopes Help prioritize maintenance workflow based on urgency and operational impact Ensure inspection recommendations and safety concerns are addressed properly Leasing, Compliance & Risk Management Oversee leasing performance and vacancy management Monitor rental pricing, renewal strategy, and market positioning Ensure compliance with company policies, lease standards, fair housing requirements, and local regulations Oversee inspection scheduling and compliance tracking Help identify operational risks and implement preventative systems Financial & Operational Oversight Monitor delinquency trends and collections performance Review operational KPIs and department metrics Assist with budgeting, forecasting, and operational planning Monitor vendor performance, staffing efficiency, and portfolio profitability Help implement scalable systems and reporting structures as the company grows Qualifications Ideal candidates will possess many of the following: Experience in residential property management leadership Experience managing staff and operational workflow Strong communication and conflict-resolution skills High-level organizational and time-management ability Experience handling owner relations and escalated tenant situations Knowledge of leasing, turnovers, maintenance coordination, and property operations Understanding of fair housing, lease enforcement, and property management compliance Ability to manage multiple priorities simultaneously Strong leadership mindset with a systems-oriented approach Experience with AppFolio or similar property management software preferred Experience managing scattered-site portfolios strongly preferred Schedule & Expectations Full-time leadership position Primarily Monday-Friday daytime schedule Some after-hours availability may occasionally be required for escalated operational issues Hybrid office and home based with occasional field visits, inspections, or owner meetings Leadership presence and responsiveness are critical to success in this role About Milestone Realty Milestone Realty is a locally owned real estate brokerage and property management company focused on residential investment properties throughout the Pittsburgh region. We specialize in scattered-site single-family and multi-family management and pride ourselves on operational efficiency, responsiveness, professionalism, and long-term client relationships. As we continue to scale, we are focused on building strong internal leadership, improving systems, and creating a professional environment where talented team members can grow with the company long-term. This is an opportunity to step into a true leadership role within a rapidly growing organization and help shape the future direction of our property management operations.

Pay:

$67,500.00 - $80,000.00 per year

Benefits:

401(k) matching Dental insurance Flexible schedule Health insurance Life insurance Paid time off Relocation assistance Retirement plan People with a criminal record are encouraged to apply

Work Location:

Hybrid remote in Aspinwall, PA 15215