Assistant General Manager

Windy City Cannabis; Carpentersville (IL); On-site; USD 55,000 - 65,000; Full time

Benefits offered by this job

Medical, Dental, and Vision Insurance

Bonus Potential 7.5% of base salary

Paid Time Off and Sick Time

401(k) Retirement Plan

Employee Discount

Job summary

Windy City Cannabis in Illinois is seeking an Assistant General Manager (AGM) to lead the dispensary alongside the General Manager. You will drive daily operations, coach staff, ensure regulatory compliance, and deliver an exceptional customer experience.

This hands-on role requires building a high-performing team, overseeing onboarding, scheduling, inventory controls, and reporting to help achieve store goals and maintain standards in a fast-paced cannabis retail environment.

Qualifications

• 3+ years of retail, hospitality, or customer-facing management experience required.
• At least 2 years of experience utilizing POS systems.
• Proven ability to lead, coach, and develop team members.
• Strong customer service, communication, organizational, and problem-solving skills.
• Ability to multitask and adapt in a fast-paced, highly regulated environment.
• Business acumen with an understanding of sales performance, labor management, inventory control, and operational reporting.
• 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.
• 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.

Responsibilities

• Lead the dispensary in partnership with the General Manager to drive performance and compliance.
• Coach and develop the team, oversee onboarding and performance management initiatives.
• Provide real-time coaching to promote accountability and growth.
• Foster a positive, inclusive, customer-focused team culture.
• Communicate operational priorities, company initiatives, and performance expectations.
• Oversee daily operations, store initiatives, and regulatory inspections/audits.
• Maintain accurate operational documentation and records.
• Support implementation of company processes and best practices.
• Track and analyze sales metrics, labor utilization, and performance indicators.
• Assist in preparing reports and identifying opportunities to improve store performance.
• Support initiatives that drive sales growth, efficiency, and customer retention.
• Assist with scheduling and workforce planning.

Skills

Retail management

POS experience

Team leadership

Customer service

Multitasking

Operational reporting

Tools

POS systems

Job description

• Base Pay $55,000.00 - $65,000.00 / Year
• Employee Type Full Time Exempt
• Manage Others Yes

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

At Windy City Cannabis, we believe cannabis should be approached with knowledge and respect. Our highly trained team provides expert guidance, personalized support, and a welcoming experience that keeps customers coming back. We foster a culture centered on education, service, accountability, and growth, where team members are empowered to make a meaningful impact.

Position Summary

The Assistant General Manager (AGM) plays a key leadership role in supporting the overall performance, compliance, and daily operations of the dispensary. Working in partnership with the General Manager, the AGM helps drive operational excellence, develop team members, maintain regulatory compliance, and deliver an exceptional customer experience.

This role serves as a hands-on leader, providing daily guidance, coaching, and support to the dispensary team while helping execute business objectives and maintain a high standard of service and accountability.

Essential Duties and Responsibilities

Leadership & Team Development

• Support the General Manager in leading, coaching, and developing dispensary team members.
• Assist with onboarding, training, and performance management initiatives.
• Provide real-time coaching and feedback to promote accountability and professional growth.
• Help foster a positive, inclusive, and customer-focused team culture.
• Communicate operational priorities, company initiatives, and performance expectations.

Operations & Compliance

• Support daily dispensary operations and store initiatives.
• Ensure compliance with company policies, security procedures, and Illinois cannabis regulations.
• Assist in preparing for and participating in regulatory inspections and audits.
• Maintain accurate operational documentation and records.
• Support the implementation and execution of company processes and operational best practices.

Inventory & Asset Protection

• Assist with inventory receiving, transfers, organization, and reconciliation.
• Conduct nightly, monthly, and compliance-related inventory audits.
• Monitor inventory accuracy and assist in resolving discrepancies.
• Ensure all inventory activities are completed in accordance with company and regulatory requirements.

Customer Experience

• Model exceptional customer service and promote a welcoming dispensary environment.
• Support the sales floor during peak business periods and assist with customer issue resolution.
• Encourage customer engagement, product education, and loyalty initiatives.
• Collaborate with leadership to continuously improve the customer experience.

Business Performance

• Track and analyze sales metrics, labor utilization , and operational performance indicators.
• Assist in preparing reports and identifying opportunities to improve store performance.
• Support initiatives that drive sales growth, operational efficiency, and customer retention.
• Assist with scheduling and workforce planning to support business needs.

Additional Responsibilities

• Maintain knowledge of cannabis products, industry trends, and regulatory requirements.
• Partner with the General Manager to achieve store goals and business objectives .
• Perform other duties as assigned.

Role Requirements

• 3+ years of retail, hospitality, or customer-facing management experience required .
• At least 2 years of experience utilizing Point of Sale (POS) systems and basic computer applications; cannabis retail experience is a plus.
• Proven ability to lead, coach, and develop team members.
• Strong customer service, communication, organizational, and problem-solving skills.
• Ability to multitask and adapt in a fast-paced, highly regulated environment.
• Business acumen with an understanding of sales performance, labor management, inventory control, and operational reporting.
• 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 maintain confidentiality, exercise sound judgment, and uphold ethical standards.
• 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.

Physical Requirements

While performing the duties of this position, employees must be able to stand or walk for extended periods, perform repetitive tasks, lift and/or move up to 10 pounds regularly (and more with assistance when necessary), communicate effectively, and accurately identify products, labels, and SKU information with or without corrective lenses.

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.

Salary Range: $55,000 - $65,000 annually

• Medical, Dental, and Vision Insurance
• Bonus Potential 7.5% of base salary
• Paid Time Off and Sick Time
• 401(k) Retirement Plan
• Employee Discount

Additional Information

This job description is intended to describe the general nature and level of work performed and is not intended to be an exhaustive list of all duties, responsibilities, or qualifications. Responsibilities may be modified at any time to meet business needs.

Windy City Cannabis is committed to equal employment opportunities for all qualified candidates and employees without regard to race, color, religion, sex, gender (including gender identity, gender expression, change of sex, and transgender status), sexual orientation, national origin, ancestry, age, military or veteran status, physical or mental disability, pregnancy, marital status, genetic information, or any other characteristic protected by applicable law. Our EEO policy applies to all terms and conditions of employment, including recruiting, hiring, placement, promotion, termination, layoff, recall, transfer, leaves of absence,compensation,and training.If you need assistance or an accommodation during the application process because of a disability, it is available upon request.

Use of Artificial Intelligence in Recruiting

Windy City Cannabis may utilize artificial intelligence (AI) or other technology-assisted tools to support portions of the recruiting and hiring process, such as organizing applications, identifying job-related qualifications, scheduling interviews, or assisting with candidate communications. All employment decisions, including candidate selection and hiring determinations, are made by qualified human decision-makers .