Dispensary Associate Jobs in Chicago Ridge, IL (NOW HIRING)

Manager in Training I

Location:In-Store
Job Type:Full Time | Exempt
Reports to: General Manager

Company Overview

Windy City Cannabis is an inviting family of hometown cannabis dispensaries where passionate Dispensary Associates connect customers to the most trusted and effective cannabis products for their lifestyle.We offer a curated selection of high-quality products, personalized service, and a warm, welcoming atmosphere that encourages customers to return again and again.

Position Summary

The Manager in Training (MIT) is an emerging leader who is preparing for future advancement into store management. This position provides hands-on experience across all areas of dispensary operations, including customer experience, inventory management, compliance, team development, and business performance. Working closely with the General Manager, Assistant General Manager,and leadership team, the Manager in Training will build the knowledge and skills necessary to successfully lead a dispensary while ensuring exceptional service and adherence to all company policies and state regulations.

Essential Duties and Responsibilities

Operations & Compliance

• Assist the General Manageror Assistant General Managerwith daily dispensary operations and execution of storeobjectives.
• Assist with inventory management, product receiving, transfers, and audits.
• Help maintain accurate cash handling procedures, register accountability, and end-of-day reconciliation processes.
• Monitor operational workflows and identify opportunities to improve efficiency, organization, and customer service.
• Assistinpreparing forandparticipating in inspections conducted by state and local regulatory agencies.
• Ensure adherence to all company policies, security procedures, and compliance requirements.

Customer Experience

• Serve as a role model for exceptional customer service and promote a welcoming, inclusive environment.
• Support the sales floor during peak business periods while helping resolve customer concerns in a professional and timely manner.
• Encourage customer engagement, product education, and loyalty-building initiatives.
• Monitor the overall customer experience and collaborate with leadership to continuously improve service standards.

Team Leadership & Development

• Work alongside management to develop leadership skills through progressive responsibility and exposure to key business functions.
• Assist with onboarding, training, and coaching new team members on operational procedures, customer service expectations, and compliance requirements.
• Provide real-time support, guidance, and recognition to team members during shifts.
• Help communicate company initiatives, operational priorities, and performance expectations to staff.
• Support workforce planning efforts, including shift coverage and staffing needs, to ensure effective daily operations.

Business Performance

• Track and analyze sales performance, operational metrics, and key business indicators.
• Assistin preparing reports andidentifying opportunities to improve store performance.
• Participate in store initiatives designed to drive revenue growth, operational excellence, and customer retention.
• Develop an understanding of labor management, scheduling, inventory controls, and overall business operations in preparation for future leadership roles.

Additional Responsibilities

• Maintain a thorough understanding of cannabis products, regulations, and industry trends.
• Complete assigned leadership development and training programs.
• Perform other duties as assigned to support the success of the dispensary and leadership team.

Role Requirements

• 2+ years of experience in a retail, hospitality, customer service, or other fast-paced, customer-facing environmentrequired.
• At least 1 year of experience in previous leadership, supervisory, keyholder, shift lead, or management experience preferred.
• Experience utilizing Point of Sale (POS) systems and basic computer applications; cannabis retail experience is a plus.
• Demonstrated ability to lead by example, coach others, and deliver exceptional customer service.
• Strong organizational, communication, problem-solving, and time management skills.
• Ability to multitask and adapt in a fast-paced, highly regulated environment.
• Must be at least 21 years of age.
• Must have open availability, including evenings, weekends, and holidays as business needs require.
• Ability to obtain and maintain a Dispensing Agent Identification Card issued by the State of Illinois.
• Ability to maintainconfidentiality, exercise sound judgment, anddemonstrate ethical conduct.
• Must remain compliant with all applicable regulatory requirements, personnel policies, safety regulations, local codes, company policies, standard operating procedures, and state and local laws governing the cannabis industry.
• Commitment to learning all aspects of dispensary operations, including inventory management, compliance, customer experience, team leadership, and business performance.
• While performing the duties of this position, the employee must be able to stand or walk for extended periods of time; use hands to perform repetitive tasks; lift and/or move up to 10 pounds regularly (and more with assistance when necessary); hear, understand, and communicate effectively; and possess visual acuity sufficient to operate equipment, read screens, and identify product information and SKU numbers, with or without corrective lenses.
• Must be able to remain attentive to detail and maintain focus while handling multiple priorities.
• Must be able to communicate clearly and effectively with customers, team members, vendors, and regulatory officials.

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.Additionalcriteria may apply based on the skills, experience, training requirements, and certifications necessary for the role.

Compensation & Benefits

Salary Range:$50,000 - $60,000 annually

Benefits

• Medical, Dental, and Vision Insurance
• Paid Time Off (PTO) and Sick Time
• 401(k) Retirement Plan
• Employee Discount
• Leadership Development and Career Advancement Opportunities
• Hands-on Management Training Program