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Regional Retail Trainer

Chicago, IL

The Regional Trainer, Retail for Sunnyside* Illinois and Arizona is responsible for leading operational training and onboarding for new and existing retail locations throughout the state. The Regional Trainer will ensure cohesive processes and procedures to best achieve operational excellence and a consistent customer and employee experience across all Sunnyside* stores. This role will work cross functionally with key partners including but not limited to Retail Ops Management, Human Resources, Compliance, Security, Marketing, New Store Development, Learning & Development and Talent Acquisition to ensure regional business needs are met.

At Sunnyside, we believe the employee experience is paramount to all. With a strong focus on training, development, diversity and authenticity, our employees experience both personal and professional growth. 

As a Regional Trainer, you will have: 

  • Experience leading and motivating new and existing dispensary teams; skills include onboarding, training, and coaching.
  • Skills in strategic thinking, decision making and complex problem solving.
  • The ability to influence and impact operational training in a dynamic hypergrowth organization.


  • You are energetic, possess strong interpersonal skills and work well with others. Collaboration is key to our team’s success!
  • You enjoy people! Consulting internal customers, understanding the business needs, and exceeding expectations!
  • You inspire others! You have a passion for coaching, developing, and influencing teams!
  • You hold yourself to an elevated high level of integrity. In an industry that is highly regulated, we trust in our employee’s commitment to always do the right thing.


  • Develop, coach, and inspire employees through their growth and development to achieve individual goals through regular feedback
  • Uphold a culture of accountability, people-centeredness and forward-thinking.
  • Support the direction of training resource planning and training needs aligning with the regional strategy.
  • Create and facilitate training resources in partnership with retail leadership to effectively support new and existing retail stores operational training needs.
  • Create, maintain, communicate and/or deliver training on SOPs, work instructions, job aids, and any other applicable training documents (including state-mandated requirements.)
  • Support change management efforts for launches of training programs/initiative including new SOPs, systems, product launches, etc.
  • Partner with store leadership to ensure execution of new hire 90-day onboarding plans and conduct on-site training when applicable.
  • Ensure timely completion of required onboarding programs and maintain accurate and timely training attendance logs.
  • Oversight of all new store opening new hire orientation including logistics planning, facilitating, and coordinating with key stakeholders to ensure a first in class onboarding experience.
  • Establish and nurture key business partner relationships across Retail Leadership, Human Resources/L&D, Compliance, New Store Development, Marketing, and IT.
  • Achieve training/onboarding objectives by maintaining onboarding checklists, training store visit reports and tracking store visits to provide visibility to retail leadership.
  • Gather data and insights from individual dispensaries to contribute to strategic plans for the region that address training and onboarding opportunities.
  • Provide retail store leaders and regional leadership with feedback during store visits and escalate concerns as deemed necessary.
  • Maintain practical subject matter expertise in all retail positions, as well as familiarity and understanding of Florida’s cannabis laws and regulations. 
  • Establish relationships with vendors to provide additional outside training programs. 
  • Frequent travel throughout regions for orientations, training, new store openings, store visits, etc.  


  • 3-5 years of retail management experience with an emphasis on training and onboarding. 
  • Professional experience in the cannabis industry preferred. 
  • Excellent written, verbal, and interpersonal communication skills. 
  • Experience with writing SOPs, work instructions, training materials and working with a Learning Management System preferred. 
  • Previous use and management of Point-of-Sale systems. 
  • Demonstrate an elevated level of professionalism and confidentiality as well as being able to relate comfortably to people at all levels of the organization and establish a rapport with trainees. 
  • Highly flexible and adaptable – working in a fast-paced industry involves daily shifting priorities; able to go with the flow and adjust to changing needs quickly. 
  • A high level of integrity, personal motivation, adaptability, and sense of urgency.
  • Ability to present in front of large audiences either virtually or in person.  
  • Ability to travel frequently to retail locations (50%-75% travel requirement dependent on regional business needs)
  • Available to work all hours of operation inclusive of nights, weekends, and holidays
  • Regular travel within the state to visit all assigned dispensaries as well periodic travel to other states for business meetings and events


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.


  • 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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