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Director of Property Management

Clear Investment Group

Chicago, IL

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JOB DETAILS
JOB TYPE
Full-time
SKILLS
Accounting, Asset Management, Budgeting, Business Plan, Business Skills, Capital Expenditure (CAPEX), Coaching, Communication Skills, Compensation and Benefits, Conflict Resolution, Construction, Construction Planning, Continuous Improvement, Contract Negotiation, Corporate Policies, Cross-Functional, Customer Support/Service, Data Analysis, Documentation, Expense Management, File Maintenance, Financial Management, Forecasting, Insurance, Investment Strategy, Lead Management, Leadership, Maintenance Services, Management Strategy, Marketing, Operational Audit, Operations Processes, Organizational Skills, Past Due Accounts, Performance Analysis, Performance Metrics, Performance Reviews, Property Maintenance, Property Management, Property Rentals, Real Estate, Regulations, Rentals, Risk, Risk Analysis, Risk Management, Team Lead/Manager, Team Player, Willing to Travel
LOCATION
Chicago, IL
POSTED
10 days ago
Director of Property Management
Department: Asset Management Group
Reports to: Executive Leadership
Location: Chicago, IL (Office-based with regular travel)
Company Overview
Clear Investment Group, LLC is a boutique real estate investment firm with a 22+ year track record, specializing in rehabilitating and stabilizing distressed C-Class multifamily assets. Based in Chicago, the firm manages portfolios across the Midwest, South, and Northeast, aiming to improve communities through strategic real estate investments.
Our Core Values are:
  1. Get it Done
  2. Ride the Wave
  3. Add Value
  4. Exhibit Passion
Position Summary
The Director of Property Management leads the performance, operations, and resident experience across Clear Investment Group’s property portfolio. This role ensures each community meets targets for occupancy, revenue, NOI, compliance, and service quality. The Director builds strong processes, coaches high-performing teams, and maintains accountability across site operations while partnering closely with Asset Management, Construction, and Leasing to protect and enhance asset value.
This is an exceptional opportunity for a driven leader seeking significant upward mobility within a rapidly growing company. We are seeking an individual who can operate at a leadership level while remaining hands-on. Somebody who sees no task as too small when it contributes to the overall success of the firm. In the early stages of this role, there will be some ground-up learning curve in order to establish foundational knowledge; however, we would perceived the right person as a tremendous asset to the organization, with endless potential for professional growth, and expansion to leadership of our firm..
CIG is seeking a candidate who embodies the qualities of an ‘Ideal Team Player’, someone who can drive impact while shaping the company’s continued growth:
  • Humble – A seasoned leader with experience who is eager to learn and grow, yet willing to roll up their sleeves to ensure tasks (large and small) are completed.
  • Hungry – A results-driven individual who pushes for excellence, sets new standards, and thrives on continuous improvement.
  • Smart – Someone who has both business acumen and people smarts—a leader who understands how to analyze data, make sound strategic decisions, and communicate effectively with a diverse team.
Compensation & Benefits
  • Base Salary: $185,000 - $225,000, commensurate with experience
  • Bonus: Performance-based incentives
  • Benefits: Comprehensive health and dental insurance, 401(k) plan, unlimitedPTO policy
Key Responsibilities
Operational Leadership
  • Oversee day-to-day property operations across all managed communities.
  • Establish and enforce operational standards, policies, and KPIs for onsite teams.
  • Ensure each property consistently meets occupancy, rent growth, delinquency, and expense targets.
  • Drive accountability through regular performance reviews, site visits, and operational audits.
Team Leadership & Development
  • Lead, coach, and develop Regional Managers, Property Managers, and onsite teams.
  • Build a strong culture of ownership, consistency, communication, and resident-first decision-making.
  • Ensure team members receive appropriate training in systems, leasing, maintenance, compliance, and customer service.
Financial & Portfolio Performance
  • Review and approve annual budgets, operating plans, and reforecasts.
  • Monitor financial performance and work with onsite teams to manage expenses, optimize revenue, and minimize delinquency.
  • Ensure rent collection processes are tight and evictions are handled professionally and compliantly.
  • Partner with Accounting and Asset Management to ensure accurate reporting and alignment with investment objectives.
Resident Experience & Service Quality
  • Oversee resident relations, service request processes, communication standards, and escalation handling.
  • Ensure properties deliver a consistent, professional resident experience that supports retention.
  • Identify and address recurring operational pain points that impact resident satisfaction or financial performance.
Compliance, Risk & Safety
  • Ensure properties adhere to Fair Housing, landlord–tenant laws, local regulations, and company policies.
  • Oversee insurance requirements, incident reporting, safety protocols, and risk mitigation.
  • Maintain proper file documentation for leasing, compliance, and operational audits.
Cross-Functional Collaboration
  • Work closely with Leasing to align marketing, lead management, and occupancy strategies.
  • Partner with Construction on CapEx planning, unit turns, and renovation execution.
  • Coordinate with Asset Management to analyze property performance, identify opportunities, and execute business plans.
Qualifications & Skills
  • 15+ years of progressive property management experience, including oversight of multi-site portfolios.
  • Strong understanding of multifamily operations, maintenance processes, Fair Housing, and financial management.
  • Experience with risk assessment, compliance, contract negotiations, and insurance planning
  • Willingness and ability to travel as often as necessary to effectively oversee portfolio performance and team operations.
  • Proven track record of leading teams, driving performance, and developing people.
  • Skilled in budgeting, forecasting, reporting, and operational analysis.
  • Strong communication, conflict resolution, and organizational skills.
  • Experience with Yardi Voyager, Excel, RentCafe, and similar property management systems preferred.
  • Experience working within EOS or a similar operating framework is a plus.

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About the Company

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Clear Investment Group