Retail Training Specialist

Retail Training Specialist 
Location: Chicago, IL
The candidate in this role will be required to travel 50-70% of the time throughout the assigned region and will be working on-site at our corporate office when not traveling.
Compensation is negotiable and will be based on qualifications and experience.

About the Role:

Are you passionate about training others and making a real impact at the store level? Join Curaleaf as a Retail Training Specialist and help shape the guest experience across our retail footprint. In this field-based role, you’ll bring national training strategies to life by supporting Store and District Managers through hands-on coaching, engaging facilitation, and performance-driven insights. You’ll be the critical connection between our learning programs and the customer experience, driving consistency, elevating performance, and fueling growth from the ground up.

What You’ll Do:

• Be a champion of Curaleaf’s culture, mission, values, and products, and share that energy with every team you train.
• Deliver in-store and virtual training sessions that focus on product knowledge, guest experience, and sales strategies.
• Reinforce training through regular store visits, live coaching, and on-the-floor support, helping teams turn learning into action.
• Collaborate closely with Store and District Managers to identify development opportunities and offer scalable, practical training solutions.
• Build strong, positive relationships with store teams, field leaders, and senior stakeholders to ensure training translates into real performance outcomes.
• Facilitate the rollout of our national training curriculum for both new and existing store teams.
• Support cross-functional initiatives by partnering with other departments to ensure our training content stays fresh, relevant, and aligned with business goals.
• Track and report on training effectiveness, offering feedback to continuously improve our programs.
• Contribute to operational excellence by optimizing training delivery and helping drive revenue through best-in-class retail practices.
• Travel extensively (50–70%) to support teams across the country — this role is for someone who thrives on the move.
• Pitch in on other training and development duties as needed — we’re a team that supports each other.

What You’ll Bring:

• A tenacious, curious mindset - you’re flexible, adaptable, and always eager to learn.
• Experience thriving in fast-paced, high-energy retail environments where priorities shift quickly.
• At least 3 years of hands-on experience in store operations, retail training, or leadership development.
• At least 2 years of experience as a Retail Store Manager.
• The ability to collaborate, influence, and build alignment across departments — even when navigating competing priorities.
• A calm, confident, and solutions-oriented approach, especially when things get hectic.
• A people-first attitude with a natural ability to build trust through clear, honest communication.
• Strong interpersonal and coaching skills, you know how to connect with team members at every level and inspire action.
• An entrepreneurial spirit and a strategic mindset, you don’t just follow the playbook, you help rewrite it.
• Self-starter energy with strong time management and organizational chops.
• A coachable mindset with a genuine desire to grow the brand by developing and empowering others.
• Impeccable attention to detail and the ability to stay organized while supporting teams nationwide.
• Solid tech skills - you’re comfortable with Microsoft Office Suite (Outlook, Excel, PowerPoint, Teams)

Even Better If You Have:

• Experience working with learning management systems (LMS) or training platforms like Cornerstone.
• Experience with tools like Tableau or PowerBI

Physical Requirements:

While performing the duties of this Job, the employee is regularly required to walk, sit, stand, talk or hear, use hands to finger or feel, and reach with hands and arms. The employee is occasionally required to climb and balance, stoop, kneel, crouch, or crawl, and lift up to 50 lbs.

This position has allergen warnings - Potential exposure to dust, pollen, and plant pathogens and requires a high-stress tolerance, adaptability, and flexibility. Ability to work in an ever-changing environment.