Senior Manager, Real Estate & Property Management

sunnyside

Chicago, Illinois, United States · Chicago · United States

Posted Jul 13, 2026

Part-time
Real Estate

Apply on company site

Job description

COMPANY OVERVIEW

Cresco Labs is one of the largest public, vertically integrated, multistate operators in the cannabis industry. Our portfolio of in-house cultivated and manufactured brands features some of the highest quality, most awarded and most popular cannabis products in America. With dozens of locations nationwide, our owned and operated Sunnyside® dispensaries provide a welcoming, positive, judgement-free place to shop for anyone at any point on their cannabis journey.

Founded in 2013, Cresco Labs’ mission is to normalize and professionalize cannabis through our passionate employees. As stewards of the cannabis industry, our teams are constantly focused on supporting the needs of our fellow colleagues, consumers, customers, and communities alike. With a focus on Social Equity and Educational Development, our SEEDTM initiative ensures that our company reflects the communities in which we serve, ensuring equal opportunity for all to have the knowledge and resources to work in and own businesses in cannabis.

At Cresco Labs, we aim to revolutionize and lead the nation’s cannabis industry with a focus on quality and consistency of product, and to bring legitimacy to the industry with the highest level of integrity and professionalism.

If you’re interested in joining our mission, click the below links to join our team today!

MISSION STATEMENT

At Cresco, we aim to lead the nation’s cannabis industry with a focus on regulatory compliance, product consistency, and customer satisfaction. Our operations bring legitimacy to the cannabis industry by acting with the highest level of integrity, strictly adhering to regulations, and promoting the clinical efficacy of cannabis. As Cresco grows, we will operate with the same level of professionalism and precision in each new market we move in to.

JOB SUMMARY

The Senior Manager, Real Estate plays a critical role in executing Cresco Labs’ real estate strategy across an active, multistate portfolio. This role carries equal responsibility across two core areas: property management and lease administration for existing locations, and transaction execution supporting new site development and M&A activity. The ideal candidate has hands on experience negotiating commercial leases, managing landlord relationships through complex issues, and supporting acquisition due diligence under tight timelines. This role reports to the Senior Director, Real Estate and works closely with corporate development, legal, construction, and operations teams. Cannabis industry experience is not required, but candidates should be comfortable operating in a highly regulated, fast moving environment with significant ambiguity.

CORE JOB DUTIES

Transactions and M&A

Conduct market research and site evaluation to identify growth opportunities for new dispensary and production locations
Lead end to end transaction management for new leases, acquisitions, and dispositions, ensuring compliance with legal and regulatory requirements
Draft and negotiate letters of intent, term sheets, and purchase and sale agreements in coordination with counsel
Support M&A due diligence on real estate matters, including lease review, title and survey review
Prepare investment memos, deal summaries, and other materials to support deal approval
Coordinate with construction and facilities teams to align site readiness with operational and regulatory timelines
Engage and manage external consultants, brokers, appraisers, and legal advisors supporting real estate activity

Property Management and Lease Administration

Manage day to day landlord relationships across an active multistate portfolio, including dispensary, cultivation, and production sites
Review and negotiate lease amendments, estoppel certificates, subordination agreements, and assignment and consent documents
Lead lease administration functions including rent schedules, straight line rent calculations, CAM reconciliations, and critical date tracking
Resolve landlord disputes, default notices, and early termination requests, coordinating with legal counsel as needed
Maintain lease abstracts, landlord responsibility trackers, and portfolio reporting tools
Provide leadership and guidance to the property management function, including direct supervision of assigned staff

REQUIRED EXPERIENCE, EDUCATION AND SKILLS

Minimum of 7 years of commercial real estate experience (residential real estate experience does not qualify)
Bachelor’s degree in real estate, finance, or a related discipline
Demonstrated experience negotiating commercial leases and managing landlord relationships independently
Excellent organizational, quantitative, writing, and communication skills
Ability to manage multiple concurrent workstreams with minimal oversight and shifting priorities
Strong Excel and PowerPoint skills; experience with mapping or GIS tools is a plus
Comfortable interfacing directly with landlords, brokers, and legal counsel
Willing to travel 20% of the time

BENEFITS

Cresco Labs is proud to offer eligible employees a robust offering of benefits including, major medical, dental and vision insurance, a 401(K)-match program, FSA/HSA programs, LTD/STD options, life insurance and AD&D. We also offer eligible employees paid holidays and paid time off. Other rewards may include annual discretionary bonuses, stock options as well as participation in our employee discount program. Benefits eligibility for permanent positions may vary by full-time or part-time roles, location, or position.

In accordance with any local and state compensation laws, the compensation listed is the current estimated range for the position. Final offer details and future compensation may be determined by multiple factors including but not limited to, geographic location, market compensation data, skills, experience, and other relevant factors. For questions about this please discuss with your recruiter during the interview process.

Pay Range

$110,000—$135,000 USD

ADDITIONAL REQUIREMENTS

Must be 21 years of age or older to apply
Must comply with all legal or company regulations for working in the industry
The company does not offer employment-based visa sponsorship for this role or any other position, now or in the future. Applicants must be legally authorized to work in the United States on a permanent basis without the need for current or future sponsorship at any time.

Cresco Labs is an Equal Opportunity Employer and all applicants will be considered without attention to race, color, religion, sex, sexual orientation, gender identity, national origin, veteran, or disability status.

California Consumer Privacy Act (“CCPA”) Notice to Applicants: Please read the California Employee Privacy Notice (“CA Privacy Notice”) regarding Sunnyside* and its affiliate Cresco Labs’ policies pertaining to the collection, use, and disclosure of personal information. This CA Privacy Notice supplements the information contained in the Sunnyside* Privacy Policy and applies to California resident employees and job applicants. Applicants with disabilities may access this notice in an alternative format by contacting CCPAnotice@crescolabs.com Reporting a Scam:

Cresco Labs is aware of fictitious employment offers being circulated from various sources. Many of these schemes consist of an alleged offer of employment with Cresco Labs with the intention of gaining personal information, including payment and/or banking information. Be aware that fraudulent job offers and correspondence may appear legitimate: they may feature a Cresco Labs logo, they may appear to originate from an official-looking email address or web site, or they may be sent by individuals purporting to represent Cresco Labs or an entity which includes the word Cresco Labs in its name.

Please note that Cresco Labs does not ask for payment or personal banking information as a condition of employment. Any personal information is requested for payroll or state badging purposes only. Applications can be securely submitted through our career’s pages.We are working diligently to block this from happening. Beware if an offer of employment looks too good to be true. Never divulge personal and banking information or send money if you are unsure of the authenticity of an email or other communication in the name of Cresco Labs.If you are in doubt, please contact us at Report-a-spam@crescolabs.com with questions.