Assistant to the Director of Retail

Department: Retail Operations
Reports To: Director of Retail Operations
Location: Multi-Store / Field-Based
Stores Supported: 4 Retail Dispensary Locations
Employment Type: Full-Time

Position Summary

The Assistant to the Director of Retail supports the Director of Retail Operations in overseeing the day-to-day performance, consistency, compliance, and continued development of four cannabis retail locations.

This position serves as an operational link between the Director of Retail, General Managers, and store-level teams. The role is responsible for helping ensure company initiatives are executed consistently, operational expectations are being met, issues are identified and addressed quickly, and each location has the support necessary to achieve its sales, staffing, compliance, and customer service goals.

The ideal candidate is highly organized, comfortable working across multiple locations, able to identify operational issues independently, and capable of balancing administrative responsibilities with hands-on retail support.

Key Responsibilities

Multi-Store Operations Support

• Assist the Director of Retail with oversight of four dispensary locations.
• Conduct regular store visits to evaluate overall operations, organization, customer experience, staffing, and execution of company standards.
• Follow up with General Managers regarding operational priorities, outstanding tasks, deadlines, and corrective actions.
• Help identify inconsistencies between locations and work with management to establish standardized practices.
• Assist with store openings, operational changes, special projects, and company-wide retail initiatives.
• Provide additional on-site leadership support when a location is experiencing staffing, management, or operational challenges.
• Serve as an additional point of contact for General Managers when the Director is unavailable.

General Manager Support & Accountability

• Maintain regular communication with General Managers regarding store performance and operational needs.
• Assist with weekly and monthly GM reporting.
• Track action items from management meetings and ensure appropriate follow-through.
• Help General Managers identify staffing, training, performance, and scheduling needs.
• Support the Director in holding store leadership accountable to company expectations.
• Help prepare agendas, reports, and supporting materials for GM meetings.
• Identify recurring store-level issues and escalate significant concerns to the Director.

Sales & Performance

• Review daily, weekly, and monthly store sales performance.
• Assist in tracking KPIs such as net sales, transactions, average basket/cart, discounts, product performance, and customer traffic.
• Identify trends and opportunities within individual stores.
• Assist the Director and General Managers in developing action plans for underperforming locations or metrics.
• Monitor execution of promotions, pricing initiatives, loyalty programs, and company sales strategies.
• Work with store leadership to identify opportunities to increase traffic, conversion, customer retention, and average transaction value.
• Assist in compiling retail performance information for presentation to executive leadership.

Staffing & Scheduling

• Review store schedules to help ensure appropriate coverage based on traffic, sales trends, and operational needs.
• Identify potential staffing shortages, excessive labor, scheduling gaps, or coverage concerns.
• Assist General Managers with staffing plans and cross-store coverage when necessary.
• Support hiring, onboarding, training, and employee development initiatives as directed.
• Help identify high-performing employees with potential for advancement.
• Assist with documentation and follow-up related to employee performance when appropriate.

Compliance & Operational Standards

• Support compliance with Massachusetts Cannabis Control Commission regulations and company policies and procedures.
• Conduct routine operational checks during store visits.
• Assist management in identifying and correcting compliance or procedural deficiencies.
• Monitor completion of required store logs, documentation, training, and operational checklists.
• Help ensure inventory handling, security procedures, cash controls, opening/closing procedures, and other regulated processes are being followed consistently.
• Immediately escalate significant compliance, security, safety, or operational concerns to the Director of Retail and appropriate leadership.

Inventory & Merchandising

• Monitor store inventory levels and identify product availability or assortment concerns.
• Work with appropriate departments and store leadership to improve product availability and merchandising execution.
• Help ensure promotional materials, menus, displays, and merchandising standards are implemented consistently.
• Communicate recurring customer requests and product feedback to the appropriate departments.
• Identify opportunities to improve product placement and the overall retail shopping experience.

Cross-Department Coordination

• Assist the Director of Retail in communicating retail needs to Marketing, Production, HR, Compliance, Maintenance, Inventory, and other departments.
• Track outstanding requests affecting store operations and follow through until resolved.
• Help coordinate company-wide initiatives across all four retail locations.
• Ensure important information from corporate leadership is communicated clearly to store management.

Administrative & Reporting Responsibilities

• Maintain organized records of store visits, action items, operational concerns, and follow-up items.
• Prepare weekly summaries for the Director of Retail highlighting store performance, staffing concerns, compliance issues, and priorities.
• Maintain operational trackers and spreadsheets.
• Assist with scheduling meetings, gathering information, preparing reports, and documenting follow-up items.
• Complete special projects assigned by the Director of Retail.

Qualifications

• 2+ years of retail operations or management experience preferred.
• Cannabis retail experience strongly preferred.
• Experience supporting or managing multiple retail locations is a plus.
• Strong organizational and follow-through skills.
• Ability to analyze basic retail sales and operational data.
• Strong written and verbal communication skills.
• Comfortable providing direction and constructive feedback to store-level leadership.
• Ability to manage multiple priorities across several locations.
• Ability to maintain confidentiality when handling employee and company information.
• Working knowledge of Massachusetts cannabis regulations preferred.
• Reliable transportation and ability to travel regularly between all four retail locations.
• Flexible availability when operational needs require additional support.

Core Competencies

Successful candidates should demonstrate:

• Operational Awareness – Able to walk into a store and quickly identify what is working and what requires attention.
• Accountability – Consistently follows up on assignments and holds others to established expectations.
• Organization – Effectively manages priorities across four locations without losing track of details.
• Communication – Communicates clearly with General Managers, employees, the Director, and other departments.
• Problem Solving – Identifies problems and proposes solutions rather than simply escalating every issue.
• Leadership Presence – Able to provide support and direction while maintaining positive working relationships with store leadership.
• Adaptability – Comfortable shifting priorities based on changing retail needs.
• Compliance Mindset – Understands the importance of operating within a highly regulated cannabis environment.

Role Expectations

This position is intended to increase the operational capacity of the Director of Retail. The Assistant to the Director should progressively take ownership of routine follow-up, store visits, reporting, operational audits, and cross-store coordination so the Director can remain focused on higher-level retail strategy, financial performance, leadership development, and company-wide initiatives.

The Assistant does not replace the General Managers' responsibility for running their individual stores. Instead, the position helps ensure that General Managers are supported, held accountable, and consistently executing the expectations established by the Director of Retail and company leadership.

Salary

$60000 - $68000 USD per year