Director of Asset Management
Salary undisclosed
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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:
The Director of Asset Management holds a key leadership role, responsible for overseeing and driving the financial and operational performance of our 3,500 – 7,000-unit multifamily portfolio, that is continuously evolving. This team member will be accountable for executing asset strategies, ensuring properties meet underwriting projections, and leading the regional management team to maximize value and efficiency across portfolio assets. The role requires a strong grasp of financial concepts, a strategic mindset, and leadership expertise to foster collaboration across departments and with external stakeholders.
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 an executive level while remaining hands-on—a leader 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:
Portfolio & Financial Oversight
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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:
- Get it Done
- Ride the Wave
- Add Value
- Exhibit Passion
The Director of Asset Management holds a key leadership role, responsible for overseeing and driving the financial and operational performance of our 3,500 – 7,000-unit multifamily portfolio, that is continuously evolving. This team member will be accountable for executing asset strategies, ensuring properties meet underwriting projections, and leading the regional management team to maximize value and efficiency across portfolio assets. The role requires a strong grasp of financial concepts, a strategic mindset, and leadership expertise to foster collaboration across departments and with external stakeholders.
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 an executive level while remaining hands-on—a leader 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
- Base Salary: $200,000 - $250,000, commensurate with experience
- Bonus: Performance-based incentives
- Benefits: Comprehensive health and dental insurance, 401(k) plan, unlimited PTO policy
Portfolio & Financial Oversight
- Develop and execute strategic asset management plans to optimize NOI, cash flow, and long-term value creation
- Monitor income, expenses, and asset-level financials, ensuring all properties adhere to underwriting standards
- Analyze property performance metrics, identifying trends, risks, and opportunities for improvement
- Identify opportunities for asset acquisition, disposition, and repositioning to enhance portfolio performance
- Prepare and present detailed asset reports to executive leadership, investors, and stakeholders
- Oversee and direct regional managers, holding them accountable for property-level performance
- Collaborate with finance, operations, acquisitions, and legal teams to align asset strategies with company goals
- Maintain oversight of capital improvement projects, ensuring efficient budgeting, project management, and adherence to company performance models/metrics
- In conjunction to the inhouse technology leader, drive the implementation of technology and data analytics tools to enhance decision-making and reporting
- Conduct regular portfolio reviews, making strategic adjustments to improve operational efficiencies
- Build a culture of continuous improvement, driven by a comprehensive view of budgeting and variance analysis at the asset level
- Ensure regulatory compliance, and local laws
- Develop and implement risk mitigation strategies, including insurance, liability protections, and financial risk management
- Oversee the negotiation and execution of contracts related to asset management activities
- Establish and maintain relationships with investors, lenders, and industry partners to support asset performance
- Continue the buildout and lead a high-performing asset management team, including regional managers, analysts, and support staff
- Provide ongoing mentorship, professional development, and performance evaluations
- Foster a culture of continuous improvement, accountability, and innovation within the asset management team
- Champion sustainability and operational efficiency initiatives to reduce costs and enhance asset longevity
- Education: Bachelor’s degree in Finance, Business Administration, Real Estate, or related field
- Experience: Minimum 10 years in property management, with at least 5 years in a senior leadership role overseeing multifamily portfolios of 3,500 – 7,000 units or more
- Industry Expertise: Strong knowledge of investment strategies, financial markets, and regulatory requirements in real estate
- Technical Proficiency: Proficiency in financial analysis, Excel, Yardi Voyager, RentCafe, and other asset management tools
- Analytical & Strategic Thinking: An understanding of financial statements, market trends, and operational performance to make data-driven decisions
- Leadership & Communication: Strong ability to lead teams, collaborate cross-functionally, and present to executive leadership and investors
- Risk Management: Experience with risk assessment, compliance, contract negotiations, and insurance planning
- Project & Time Management: Proven ability to manage multiple projects, prioritize tasks, and execute asset-level strategies efficiently
- Travel Requirement: Willingness and ability to travel as often as necessary to effectively oversee portfolio performance and team operations
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