Vice President, Retail Operations


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 senior member of the Sunnyside* Retail Leadership team, the Vice President of Retail Operations will oversee the entire  network of Sunnyside* Dispensaries across the United States.  Based in Chicago, IL, this  role will oversee the Regional Directors across  25+ Dispensaries nationwide. The VP of Retail Operations will oversee the successful execution of visual merchandising and event execution standards for the network, as well as being a strategic driver and inspirational leader to deliver the best-in-class retail experience in the industry. Additionally, the role will drive strategic revenue focused tactics while delivering on budget costs and recognizing efficiencies across the retail operation. The ideal candidate will exude excitement for entrepreneurship while also serving as a key liaison with cross-functional leaders including HR, Merchants, Marketing, Visual, Training & Development, Maintenance, Security, and Compliance.  


Create and implement the national retail operations plan to support the execution of multi-region and company initiatives, ultimately driving consistency and accountability to sales plans and cost structures for each region and each dispensary.

Manage with integrity, honesty and knowledge that promotes the culture, values and mission of Cresco Labs and Sunnyside*.

Deliver a ‘People First’ mantra focused on the core values of Cresco Labs, including but not limited to leadership, ownership, and stewardship.

Lead the field teams with positive influence through clear, concise communication, while developing an environment that evokes passion and excitement for the industry and the company.

Continuously engage with the field team to provide career growth opportunities while also delivering constant feedback along with the tools needed to achieve long term professional growth.

In partnership with Training & Development leaders, collectively deliver the tools that allow dispensary managers to operate with autonomy and creativity while also operating within measurable guidelines.

Drive accountability for each aspect of the dispensary operation through the Division of Responsibility (DOR) program. The three DOR workstreams (Talent, Dispensary Experience, Operations) to be measured by strategic tactics with detailed milestones to mark continuous improvement.

Champion programs that further imbed Cresco Labs and Sunnyside* into the local community, including unique team building events that focus on volunteerism and integration into each neighborhood we serve.

Create the toolkit that strives for data-driven decisions to further optimize the operations of the Dispensary:

Daily/Weekly/Monthly focus on critical Key Performance Indicators (KPI’s); deep dive to further evaluate opportunities for growth and improvement.

Instill measurement tactics to drive enhanced transaction throughput while also recognizing the need to deliver personalized interactions with each customer and evolving the customer journey.

Consistently evaluate staffing levels to optimize peak/non-peak day throughput both front of house and back of house.

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

In partnership with the Regional Directors, consistently inspire and execute localized events, including Cresco House of Brand (HOB) experiences and 3rd party pop-ups, as well as Outreach Programs, to optimize marketing tactics within the region to 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, including the timely and successful state inspections 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 within each region.

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

Detailed comprehension of dispensary inventory and point-of-sale (POS) systems with a keen sense of awareness to continuously improve system output, acting as the key partner to drive system enhancements with IT and Compliance.


Bachelor’s degree or work equivalent

Minimum of 10 years Retail Management Experience, specifically in a high-growth environment with multiple locations across multiple states; flagship volume experience

District/Region or equivalent level experience across multiple states (10+ years)

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

Experience developing requirements needed for successful implementation of tools to analyze specific operations tactics as well as financial reports

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

Experience in a complex, fast-paced environment

Ability to manage the overall operations of multiple stores independently

Organization and planning skills

Team-building skills

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

Ability to travel throughout multiple locations up to 50% of the 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