Regional Retail Director


Chicago, IL, USA

Full time

Aug 5

This job is no longer accepting applications.


Recently named one of Entrepreneur magazine’s Top 100 Cannabis Leaders, Cresco Labs is one of the largest vertically-integrated multi-state cannabis operators in the United States. Cresco is built to become the most important company in the cannabis industry by combining the most strategic geographic footprint with one of the leading distribution platforms in North America. Employing a consumer-packaged goods (“CPG”) approach to cannabis, Cresco’s house of brands is designed to meet the needs of all consumer segments and includes some of the most recognized and trusted national brands including Cresco, Remedi and Mindy’s, a line of edibles created by James Beard Award-winning chef Mindy Segal. Sunnyside*, Cresco’s national dispensary brand is a wellness-focused retailer designed to build trust, education and convenience for both existing and new cannabis consumers. Recognizing that the cannabis industry is poised to become one of the leading job creators in the country, Cresco has launched the industry’s first national comprehensive Social Equity and Educational Development (SEED) initiative designed to ensure that all members of society have the skills, knowledge and opportunity to work in and own businesses in the cannabis industry. 


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.


As a member of the Sunnyside* Retail Leadership Team, the Regional Director (RD), will oversee the four-wall retail environment for multiple dispensaries located in the state of Illinois.  The RD will be responsible for delivering the best-in-class retail experience that is patient and customer centric while focused on the training and development of our retail team members. The role will continuously build industry-leading best practices while delivering enhanced metrics tied to compliance, customer and patient satisfaction, and operational excellence tactics. Cross-functional partnerships will be critical to the success of the candidate, identifying opportunities for continuous improvement with the overall efficiency of the dispensaries. The leader will serve as the key liaison between Retail Senior Leadership, multiple Dispensary Managers, as well as numerous day-to-day partners including: Human Resources, Talent Acquisition, Merchants, Marketing, Visual, Training & Development, Security, and Compliance.

The role will be critical to the future success of the Sunnyside* Retail Organization as we further optimize the profitability of each dispensary.  The candidate must exude excitement for entrepreneurship as we continue to chart the dispensary operational playbook, while also having an appreciation of the unique nuances that are part of the initial foundation of what makes retail at Cresco unique.


Create and implements the regional plan to support the execution of regional and company initiatives, ultimately driving consistency and accountability to plans

Manages with integrity, honesty and knowledge that promote the culture, values and mission of Cresco and Sunnyside*

Direct day to day leader of multiple Dispensary Managers

Additional oversight of each dispensary leadership team including Assistant Dispensary Managers, Inventory Managers and Lead Wellness Advisors

Core focus on career development, leaderships skills, and team member engagement while being the constant source of motivation and support for the region

Inspirational leadership drivers, balancing celebratory achievements at the store and individual contributor level, while course-correcting any shortfalls requiring consistent documentation

Development of each dispensary leadership team member, including direct partnership with Talent Acquisition to recruit, hire and onboard the best talent in the industry

Driver of training materials execution (product, procedural, compliance), focused on consistent rollout tactics for the entire regional team; timeliness is critical while also providing feedback for continuous improvement of materials provided

Core Operational Excellence tactics including Dispensary schedules (team and operational hours), inventory efficiencies, IT/Equipment enhancement rollouts, online + in-store customer/patient journey flow

Oversight of the strategic revenue plans for each dispensary within the region, including merchant team and planning team partnership to ensure appropriate product mix and consistent execution of the promotional cadence tactics

Localized event execution, including Cresco House of Brand (HOB) events and 3rd party pop-up; creative input from the store team is important as we further optimize varying strategic marketing tactics within the region

Consistent focus on the Outreach Program, further optimizing levers that continuously drive new patient and customer awareness

Day to day focus of regulatory compliance with strict adherence to all policies and procedures; collaborative working partnerships with Compliance, Security, Environmental Health & Safety (EHS) are critical to successful operation

Strong comprehension of industry trends and state governance activity to anticipate and quickly adjust to future regulatory requirements

Ensures timely and successful state inspections as required for each location

Oversee accurate records of all dispensary activities including daily cash reconciliations, patient and customer records, sales, deliveries and returns in accordance with state laws and the standards set by company

Maintains multiple units’ inventory control system and daily counts of all cannabis and non-cannabis products in the facility

Cross functional leadership collaboration with Human Resources, Talent Acquisition, Merchants, Marketing, Visual, Training & Development, Security, and Compliance


Bachelor’s degree 

Retail Management Experience, specifically in a high-growth environment with multiple locations (10+ years)

District/Region or equivalent level experience (3+ years)

Experience analyzing financial reports

Experience in a complex, fast-paced environment

Ability to manage the overall operations of multiple stores independently

Organization and planning skills

Team-building skills

Strong business acumen including data management, attention to detail, and excellent communication and interpersonal skills

Proven experience establishing strategic goals with key stakeholders and monitoring company and individual performance through KPIs and other metrics

Proficient in MS Office, Highly Proficient in MS Excel

Demonstrated ability to learn and apply technical and product-related information in a professional consultative manner

Must maintain a high level of integrity, personal motivation, and sense of urgency

After-hours work required to manage sales facing inventory and order entry from time to time


Must be 21 years of age or older to apply

Must comply with all legal or company regulations for working in the industry

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.

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A new kind of cannabis shop