We're Hiring! Director, Leasing | Chicago, IL
We are seeking an experienced Director, Leasing to join our team in Chicago, Illinois.
Position Summary
The Director, Leasing is a senior leadership role responsible for driving leasing strategy and portfolio performance across a diversified commercial real estate portfolio. This position oversees new leasing, renewals, expansions, relocations, and strategic occupancy planning while thinking beyond transactions to maximize long-term asset value and investment returns.
This is an entrepreneurial leadership role—not a traditional brokerage position. The successful candidate thinks like an owner, takes accountability for business outcomes, challenges assumptions with sound judgement and data, and proactively identifies opportunities to improve portfolio performance. They are naturally curious, commercially minded, and motivated by creating value rather than simply completing transactions.
The successful candidate has extensive experience representing institutional landlords, developers, REITs, or owner/operators across office, industrial, retail, and development assets. They partner closely with Asset Management, Property Management, Development, Legal, Finance, and Executive Leadership to execute leasing strategies that align with broader investment objectives.
This role is based in our Chicago main office, located at 120 S. LaSalle St., Chicago, IL, and is an in-office position, five days per week.
Candidates whose experience is limited primarily to third-party brokerage representation without ownership-side accountability will generally not align with the requirements of this role.
About the Company
We are an experienced global owner and operator of strategically located commercial real estate assets across Canada, Ireland, and the United States. Our diversified portfolio includes office buildings, data centres, industrial and retail properties, residential rental communities, surface parking facilities, and hospitality assets. Backed by deep industry expertise and an entrepreneurial mindset, we take a hands-on approach to creating long-term value through operational excellence, thoughtful asset management, and strategic investment.
As an active owner and operator, we are committed to enhancing the performance and market appeal of our properties to better serve both existing and prospective tenants. Through a combination of operational excellence, customer-focused service, and targeted capital investments, we are focused on unlocking value across our portfolio while delivering exceptional outcomes for our tenants, partners, and unitholders.
Ravelin’s head office is located in Halifax, Nova Scotia.
Given the breadth of the platform and the Company’s entrepreneurial, hands-on approach to ownership and operations, the organization values adaptability, initiative, and strong cross-functional collaboration.
REQUIRED SKILLS
- Entrepreneurial mindset with the ability to think like an owner and make decisions that maximize long-term portfolio value.
- Strategic leadership with the ability to make portfolio-level leasing decisions.
- Strong commercial acumen, financial analysis capabilities, and disciplined risk assessment.
- Proven expertise in leading complex landlord-side negotiations and structuring value-enhancing transactions.
- Advanced knowledge of landlord-side leasing, lease economics, incentives, documentation, and risk management.
- Demonstrated ability to challenge conventional thinking, make sound decisions under uncertainty, and take ownership of outcomes.
- Strong leadership, communication, negotiation, and stakeholder management skills.
- Proven ability to collaborate across Asset Management, Property Management, Development, Finance, Legal, and Construction.
- Experience leading leasing professionals and portfolio-wide initiatives.
- Naturally curious with a continuous improvement mindset and the ability to identify creative solutions that enhance business performance.
- Proficiency with Yardi, Yardi Deal Manager, VTS, and related systems.
- High degree of professionalism, integrity, and market credibility.
REQUIRED EDUCATION AND EXPERIENCE
- Bachelor's degree in Business, Real Estate, Finance, Economics, Urban Land Development, or a related discipline.
- Minimum 3 – 5 years of progressive commercial leasing experience representing institutional ownership, developers, REITs, or owner/operators.
- Demonstrated success developing and executing landlord-side leasing strategies that improve occupancy, revenue, tenant retention, and asset value.
- Experience leading leasing teams and portfolio-wide leasing initiatives.
- Proven success negotiating complex lease transactions with institutional, national, and multinational tenants.
- Strong understanding of investment real estate, asset management principles, portfolio performance metrics, market analysis, financial underwriting, and forecasting.
- Brokerage experience alone is not sufficient unless complemented by meaningful ownership-side or asset management experience.
RESPONSIBILITIES
Leasing Strategy & Portfolio Performance
- Lead leasing strategy across the Chicago portfolio to maximize occupancy, revenue, tenant quality, and long-term asset value. Think like an owner by evaluating every leasing decision through the lens of value creation, investment performance, and long-term portfolio success.
- Develop innovative leasing strategies aligned with investment objectives.
- Analyze market conditions, financial performance, tenant demand, and competitive positioning.
- Challenge assumptions, broker recommendations, and traditional approaches using market intelligence and financial analysis.
- Identify opportunities to improve portfolio performance while mitigating leasing risk.
Transaction Leadership
- Lead the full leasing lifecycle from prospecting through execution.
- Negotiate complex lease transactions with local, national, and multinational tenants.
- Structure creative deals that balance tenant requirements with ownership objectives.
- Evaluate deal economics, tenant creditworthiness, and investment risk.
- Oversee renewals, lease restructurings, LOIs, amendments, and lease documentation.
Cross-Functional Leadership
- Partner closely with Property Management, Asset Management, Construction, Development, Legal, and Finance.
- Coordinate leasing decisions that support operational efficiency and long-term asset performance.
- Serve as a trusted advisor to senior leadership on leasing strategy and market opportunities.
Leadership & Relationships
- Lead, mentor, and develop the leasing team.
- Foster a culture of accountability, collaboration, innovation, and continuous improvement.
- Represent ownership in the brokerage community while building long-term tenant relationships.
Financial Leadership
- Prepare leasing budgets, forecasts, underwriting, and business plans.
- Monitor portfolio performance and provide strategic recommendations.
- Support investment committee presentations and asset planning initiatives.
WORKPLACE EQUITY AND CONFIDENTIALITY
We are committed to cultivating an inclusive, respectful, and equitable work environment where every team member feels valued. We proudly uphold fair employment practices and do not tolerate discrimination or harassment of any kind. All hiring and employment decisions are based strictly on experience, qualifications, and organizational needs.
This role operates within a confidential and proprietary business environment. Select operational policies and procedures are shared across the Clarke Inc. family of companies. Sharing, discussing, or disclosing this information with individuals outside of our organization is strictly prohibited.
Compensation
This role offers a salary range of $145,000 - $180,000 (USD). Final compensation will be based on experience, qualifications, and job-related factors.
Benefits:
- Comprehensive healthcare coverage: Medical / Vision / Dental / Prescription Drug
- 401(K) retirement plan with matching contributions
- Health Savings Account (HSA)
Pay: $145,000.00 - $180,000.00 per year
Benefits:
- 401(k)
- 401(k) matching
- Dental insurance
- Health insurance
- Health savings account
- Paid time off
- Vision insurance
Work Location: In person
