Assistant General Manager – People (Multi-Location)

Job Type: Full-time

Location: In-person, Westfield/West Springfield, MA (oversight of two dispensary locations)

As the Assistant General Manager of People at CC, you play a pivotal role in leading the charge for an unparalleled guest experience across multiple locations. Reporting to the General Manager, you excel in providing on the fly solutions and swiftly diffusing objections from both staff and customers. Your focus extends beyond operations; you are the driving force in all things people across two dispensaries. Leading coaching, development, and training initiatives, you cultivate an atmosphere of unwavering support for our dynamic teams and customers alike. If you're passionate about creating positive connections, overcoming challenges, and shaping a thriving people-centric, multi-location environment, this role is for you.

RESPONSIBILITIES

Team & Sales Excellence

Partner with the Dispensary Manager (GM) to ensure goals, targets, and accountability of teams across both locations are aligned.

Oversee both teams in achieving their day-to-day goals through consistent feedback, regular touch bases, and performance reviews aligned with RoadTrip objectives.

Maintain dispensary operations at both locations by adhering to RoadTrip’s Policies & Procedures and ensuring full compliance with state recreational cannabis regulations.

Create and sustain a strong selling culture across both stores through consistent staff training, goal setting, and incentive programs.

Maintain an active presence on the sales floors of both locations to understand performance, identify opportunities, and drive sales.

Ensure in-store marketing, signage, and customer information are current, consistent, branded, and educational across both dispensaries.

Partner with the Assistant Manager of Operations to ensure appropriate inventory levels at both locations support revenue and promotional strategies.

Monitor and analyze dispensary KPIs across both locations and align training and team behaviors accordingly.

Manage and inspire teams at both locations to deliver the highest level of customer experience.

Represent the company professionally at all times across both sites.

Team Journey

Partner with the GM to oversee teams of leads at both locations, utilizing delegation to ensure efficient daily operations.

Drive a culture of positive employee engagement across both stores, with a strong focus on inclusion and diversity.

Lead recruitment, hiring, onboarding, and training of new staff across both locations.

Ensure team efficiency through ongoing coaching, instruction, counseling, and leadership.

Identify and address employee issues in a timely manner across both locations, ensuring proper documentation and communication with HR.

Oversee all personnel-related administrative processes (performance evaluations, time sheets, status changes, etc.) for both teams.

Operational Excellence

Maintain all aspects of dispensary operations at both locations in strict compliance with Cannabis Control Commission, municipal, and state regulations.

Build and maintain positive relationships with neighboring businesses, community groups, and local stakeholders for both locations.

Effectively manage cash controls and financial reporting across both stores, ensuring accuracy in POS, cash handling, bank logs, inventory, and deposits.

Partner with the inventory managers to ensure accurate and compliant inventory records are maintained at both locations.

QUALIFICATIONS

Must be 21 years of age or older as required by the Massachusetts Cannabis Commission.

Able to pass all required background checks.

Maintain regular and punctual attendance.

Proficient in MS Office (Word, Excel) and willing to learn accounting, tracking, and inventory systems.

REQUIRED EXPERIENCE

Minimum 1–3 years of retail management experience overseeing 10+ employees; multi-location oversight strongly preferred.

Demonstrated experience in coaching, performance management, and employee development.

Experience driving sales performance, achieving KPIs, and building a strong customer-centric culture.

Experience with Massachusetts Seed-to-Sale System (METRC) required.

Experience with Dutchie POS or similar retail POS systems.

Experience working in a highly regulated environment (cannabis, pharmacy, alcohol, or similar) strongly preferred.

Proven ability to manage multiple priorities, locations, and teams in a fast-paced environment.

Strong conflict resolution and problem-solving skills with the ability to make sound decisions in real time.

PHYSICAL REQUIREMENTS

Ability to stand, walk, and remain active on the sales floor for extended periods (8+ hours per shift).

Ability to lift, carry, and move items up to 25–50 pounds (inventory boxes, supplies, etc.).

Frequent bending, reaching, and crouching to access products and assist with merchandising or inventory tasks.

Ability to work in a fast-paced retail environment with moderate noise levels and frequent customer interaction.

Ability to operate standard office and retail equipment (computers, POS systems, cash registers).

Must be able to travel regularly between both dispensary locations and have reliable transportation.

WORKING CONDITIONS

Ability to accommodate varied shifts, including evenings, weekends, and holidays.

Ability to travel regularly between both dispensary locations.

Able to assist customers with disabilities in navigating the dispensary.