Manager In Training Jobs in Winchester, VA (NOW HIRING)

Ayr Wellness is a leading U.S. multi-state cannabis operator with more than 90 licensed retail locations across Florida, Massachusetts, Pennsylvania, Ohio, New Jersey, Nevada, Virginia, and Delaware. We cultivate, manufacture, and sell a broad portfolio of high-quality cannabis products, serving both medical patients and adult-use consumers across our markets.

At Ayr, our strength is our people. We are reimagining how we operate across every part of the business and are looking for builders and doers who want to roll up their sleeves and help build what’s next. The cannabis industry is fast-moving, complex, and full of opportunity. At Ayr, you will have the opportunity to make a meaningful impact while growing your career alongside a company focused on long-term success.

At AYR Wellness, our District Managers are hands‑on leaders who drive results, grow people, and bring consistency across multiple retail locations. In Virginia, this role carries additional scope and complexity. You will operate in a medical cannabis environment today while leading the district through preparation for adult use expansion. This is not a steady‑state role. It requires building, scaling, and leading through change. Reporting to the VP Retail, the District Manager is responsible for delivering business results, developing strong store leadership teams, and ensuring a consistent, compliant, and customer‑first experience across all locations. At the same time, preparing teams, processes, and execution standards to support increased volume, pace, and operational complexity as the market evolves. This role partners closely with Operations, People Ops, Compliance, Marketing, and Asset Protection, and other support teams to build infrastructure, align priorities, and execute effectively in a highly regulated and evolving environment.

• Meet and exceed sales goals, KPIs, and operational targets.
• Manage budgets, drive ROI, and control expenses with intention.
• Effective scheduling: implement and manage practices that ensure full operational coverage during business hours and high-volume periods, maintaining pharmacist staffing levels in compliance with all regulatory requirements.
• Ensure consistent execution of retail standards across all locations.
• Maintain a strong focus on customer experience, operational discipline, and compliance.
• Drive a customer‑focused culture across all locations, with accountability for customer feedback, online reputation (including Google reviews), and consistent, high‑quality in‑store experiences.

• Coach and develop Store Managers to lead with accountability, clarity, and strong business ownership.
• Build and maintain a strong internal talent pipeline across the district.
• Identify high‑potential team members and create clear paths for development and promotion.
• Partner with People Ops and Talent team to manage performance, address issues early, and support leadership growth.

• Lead district‑wide readiness for adult use expansion, including operational planning, team capability, and execution standards.
• Ensure AYR SOPs are thoughtfully crafted to reflect market‑specific requirements and are effectively implemented across all locations.
• Prepare store teams to transition from a medical‑only model to a higher‑volume, dual‑channel environment.
• Identify gaps in staffing, processes, and execution, and build scalable solutions ahead of launch.
• Partner cross‑functionally to align retail, compliance, marketing, people operations, and asset protection in preparation for adult use.
• Ensure a smooth and compliant transition at launch, maintaining performance, customer experience, and operational control.
• Set clear expectations for pace, productivity, and execution as the market evolves.

• Ensure all locations meet state‑specific regulatory requirements, including pharmacist coverage ratios and credentialed staff.

• Support new store openings and market expansion efforts.
• Build scalable processes and operating rhythms that support growth.
• Establish consistency across locations while adapting to evolving market conditions.

• Other duties as assigned.

• Demonstrated ability to lead high‑volume cannabis retail operations in both medical and adult‑use environments, managing dual‑channel complexity and evolving state regulatory requirements.
• Strong business acumen with the ability to plan, prioritize, and deliver results.
• Experience leading teams through growth, change, or operational transformation.
• Ability to scale operations and teams in advance of increased demand and complexity.
• Strong understanding of retail performance drivers, customer experience, and team development.
• Ability to partner cross‑functionally and lead through ambiguity in evolving environments.

• College degree or equivalent experience.

• Experience operating in or leading a high‑volume dispensary or retail environment through a medical‑to‑adult‑use market expansion is required.

Ayr Wellness is an equal‑opportunity employer. We are committed to building a team that represents a variety of backgrounds, perspectives, and skills. We do not discriminate on the basis of race, color, religion, creed, national origin, ancestry, sex (including pregnancy, childbirth, or related medical conditions), sexual orientation, gender identity or expression, age, disability, genetic information, marital status, military or veteran status, or any other protected status in accordance with applicable federal, state, and local laws.

Nothing in this job description restricts management’s right to assign or reassign duties and responsibilities to this job at any time.