Manager in Training II
Windy City Cannabis Manager in Training II
Manager In Training II (MIT II)
Location: In-Store
Job Type: Full Time | Exempt
Reports to: District Manager
Company Overview
Founded in 2014, Windy City Cannabis has grown from a single dispensary to six locations across Illinois, with our flagship store proudly located in Homewood, Illinois. As a woman-owned company since 2023, we are committed to creating a safe, inclusive, and professional environment for both medical and recreational cannabis customers. We believe cannabis should be approached with knowledge and respect, which is why our highly trained team provides expert guidance and personalized support.
At Windy City, you'll be part of a passionate team that values education, customer care, and community connection. We offer a supportive and welcoming workplace where your contributions matter, your growth is encouraged, and your work truly makes a difference.
Summary
The Manager In Training II (MIT II) is a developmental leadership role designed for experienced managers who are looking to transition into the cannabis industry or further enhance their dispensary leadership experience. Through hands-on training and exposure to all aspects of dispensary operations, this role provides future leaders with the skills, knowledge, and business acumen needed to support organizational growth and pursue advanced leadership opportunities within Windy City Cannabis. The MIT II partners closely with General Managers and District Managers to develop expertise in operations, compliance, team development, customer experience, and financial performance.
Essential Duties and Responsibilities
Operations & Compliance
- Support the execution of daily dispensary operations while ensuring compliance with company policies and state regulations.
- Develop proficiency in inventory management, audits, deliveries, transfers, and cash-handling procedures.
- Assist with regulatory inspections and maintain accurate operational records.
- Identify opportunities to improve operational efficiency, organization, and overall store performance.
Customer Experience
- Model and promote exceptional customer service standards.
- Support the sales floor and assist with resolving customer concerns.
- Foster a welcoming environment that drives customer engagement, loyalty, and retention.
- Help maintain a clean, organized, and customer-focused store environment.
Leadership & Team Development
- Lead, coach, and support team members to drive engagement, accountability, and performance.
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Assist with hiring, onboarding, training, and ongoing development of dispensary staff.
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Communicate priorities, provide feedback, and support a positive team culture.
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Develop the leadership skills necessary to independently manage a dispensary team.
Business Performance
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Monitor sales, labor, inventory, and operational metrics to support business goals.
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Assist in analyzing reports and identifying opportunities to improve performance.
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Gain experience in scheduling, labor management, inventory control, and financial accountability.
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Partner with store and district leadership on initiatives that support growth and operational excellence.
Additional Responsibilities
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Complete all leadership development and training requirements.
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Maintain a thorough understanding of cannabis products, regulations, and industry trends.
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Perform other duties as assigned.
Role Requirements
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3+ years of retail management experience, including experience as an Assistant General Manager, Store Manager, or comparable leadership role.
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Experience leading teams in a high-volume retail, hospitality, or regulated environment preferred.
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Strong understanding of inventory management, compliance, staffing, and customer service operations.
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Demonstrated leadership skills with the ability to coach, develop, and motivate employees.
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Business acumen with knowledge of sales performance, labor management, and operational metrics.
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Must be at least 21 years of age.
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Must have open availability.
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Ability to obtain and maintain a Dispensing Agent Identification Card issued by the State of Illinois.
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Ability to maintain confidentiality and exercise sound judgment.
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Strong communication, organizational, and problem-solving skills.
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Must remain compliant with all company policies, regulatory requirements, and state and local laws applicable to the cannabis industry.
Internal Candidates
All Team Members who have successfully completed six (6) months of employment in their current position and are in good standing will be considered for promotion and are encouraged to apply to open positions. Being in "good standing" means an accrual of fewer than five attendance points and fewer than seven cash handling points. Additional criteria may apply based on the skills, experience, training requirements, and certifications necessary for the role.
Compensation & Benefits
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Salary Range: $60,000 - $70,000 annually
Benefits
- Medical, Dental, and Vision Insurance
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Paid Time Off and Sick Time
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401(k)
40% Employee Discount
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Employee Samples
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Leadership Development and General Manager Training Program
The above job description summarizes the role responsibilities and is not intended to be all inclusive, it may change from time to time.
Windy City Cannabis provides equal employment opportunities to all employees and applicants for employment and prohibits discrimination and harassment of any type without regard to race, color, religion, age, sex, national origin, disability status, genetics, protected veteran status, sexual orientation, gender identity or expression, or any other characteristic protected by federal, state or local laws.
This policy applies to all terms and conditions of employment, including recruiting, hiring, placement, promotion, termination, layoff, recall, transfer, leaves of absence, compensation and training.