Full-Time

Senior Manager

Real Estate & Property Management

Updated on 9/3/2026

Sunnyside

Sunnyside

Retailer of medical and adult-use cannabis

Compensation Overview

$110k - $135k/yr

+ Annual discretionary bonuses + Stock options

No H1B Sponsorship

Chicago, IL, USA

In Person

Travel up to 20% of the time is required.

Bachelor's

Category
Real Estate (2)
,
Required Skills
Market Research
Mergers & Acquisitions (M&A)
Excel/Numbers/Sheets
PowerPoint/Keynote/Slides
Requirements
  • 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 independently managing landlord relationships.
  • Excellent organizational, quantitative, writing, and communication skills.
  • Ability to manage multiple concurrent workstreams with minimal oversight and shifting priorities.
  • Strong Excel and PowerPoint skills.
  • Ability to interface directly with landlords, brokers, and legal counsel.
  • Must be 21 years of age or older to apply.
  • Must comply with all legal or company regulations for working in the industry.
  • Must be legally authorized to work in the United States on a permanent basis without current or future sponsorship.
Responsibilities
  • 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 while 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 real estate M&A due diligence, including lease review and 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.
  • Manage day-to-day landlord relationships across an active multistate portfolio of 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 in coordination 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.
Desired Qualifications
  • Experience with mapping or geographic information system tools.

Sunnyside is a national cannabis dispensary brand under Cresco Labs that sells medical and recreational cannabis through a network of stores across multiple states. The company operates both in-person retail and online ordering for in-store pickup, with some markets offering home delivery. Stores emphasize a bright, wellness-focused shopping environment designed to be approachable for first-time and experienced cannabis users, and they employ trained wellness advisors to help customers choose products. Sunnyside carries a wide range of products, including flower, vapes, edibles, concentrates, and topicals, featuring many Cresco-backed brands (such as Cresco, High Supply, FloraCal, Mindy’s Edibles, Good News, Wonder, and Remedi) alongside products from other operators and local producers. The goal is to normalize cannabis shopping, educate customers, and provide easy access to cannabis products as the brand expands across the U.S.

Company Size

N/A

Company Stage

N/A

Total Funding

N/A

Headquarters

Leicester, United Kingdom

Founded

2018

Simplify Jobs

Simplify's Take

What believers are saying

  • Ohio expansion accelerated in April and May 2026, adding Bridgeport and Aberdeen locations.
  • Second-quarter 2026 revenue reached $173 million, with $40 million adjusted EBITDA and 22.8% margin.
  • The March 26, 2026 Wyomissing contract settled, reducing strike risk and improving retention.

What critics are saying

  • Teamsters struck Sunnyside Wyomissing on February 26, 2026, exposing labor unrest and wage pressure.
  • Cresco carried $311 million term debt and only $67 million cash on June 30, 2026.
  • Cannabis licensing remains state-fragmented; one adverse Ohio, Florida, or Illinois rule change hits store economics.

What makes Sunnyside unique

  • Sunnyside couples retail wellness branding with Cresco Labs' house brands and education-first advisors.
  • The chain spans 74 stores nationwide after Aberdeen and Bridgeport openings in May 2026.
  • Sunnyside uses omnichannel pickup and selective delivery, increasing convenience across mature cannabis markets.

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Benefits

Health Insurance

Dental Insurance

Vision Insurance

401(k) Retirement Plan

401(k) Company Match

Paid Holidays

Paid Time Off

Stock Options

Company News

Associated Press
Apr 10th, 2026
Cresco Labs opens seventh Ohio cannabis dispensary in Bridgeport

Cresco Labs has opened its seventh Ohio dispensary, Sunnyside Bridgeport, located at 435 Main Street in Bridgeport. The new location marks the company's 73rd dispensary nationwide. The store is situated in downtown Bridgeport near the Ohio River, close to I-70 and U.S. Route 40. It offers cannabis products from Cresco Labs' brand portfolio, including Cresco, Supply, Good News, Mindy's and Wonder, along with accessories. Customers aged 21 and older can shop in-store or order online for pickup. The dispensary operates daily from 9 a.m. to 9 p.m. CEO Charlie Bachtell said the opening brings the company's "education-first approach" to more consumers across Belmont County and the Ohio Valley region.