Retail Training Specialist

Curaleaf; Chicago (IL); On-site; USD 62,000 - 70,000; Full time

Benefits offered by this job

Medical, dental, and vision insurance

Health Savings Account (HSA) and/or FS

Employee Assistance Program (EAP)

Wellness program and challenges

Gym discounts

401(k) retirement plan with company “

Life and disability insurance

Supplemental insurance options (e.g.,/

Commuter benefits

Paid time off (PTO) including vacation

Parental leave

Bereavement leave

Employee discounts

Recognition programs

Pet insurance

Job summary

Curaleaf is seeking a Retail Training Specialist to support store teams nationwide. The role emphasizes coaching, delivering in-store and virtual sessions, and driving guest experience improvements.

You will travel 50–70% and partner with Store/District Managers to implement national training curricula, ensuring programs stay relevant and impactful.

Qualifications

• A tenacious, curious mindset; flexible, adaptable, eager to learn.
• Experience thriving in fast-paced, high-energy retail environments.
• 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.

Responsibilities

• Be a champion of Curaleaf’s culture, mission, values, and products.
• Deliver in-store and virtual training sessions focusing on product knowledge, guest experience, and sales strategies.
• Reinforce training through store visits, live coaching, and on-the-floor support.
• Collaborate with Store and District Managers to identify development opportunities and scalable training solutions.
• Track and report on training effectiveness and continuously improve programs.

Skills

Retail Training

Store Operations

Leadership Development

Coaching

Communication

Time Management

Organizational Skills

Cross-functional Collaboration

Tools

LMS

Cornerstone

Tableau

PowerBI

Job description

• Bereavement leave

At Curaleaf, we’re redefining the cannabis industry with a strong commitment to quality, expertise, and innovation. As a leading global cannabis provider, our brands—including Curaleaf, Select, and Grassroots—offer premium products and services in both medical and adult-use markets.

Join us at Curaleaf to be part of a high-growth, purpose-driven company that champions corporate social responsibility through our Rooted in Good initiative, supporting community outreach and positive change. Here, you’ll have the opportunity to make a meaningful impact, drive innovation, and help shape the future of cannabis.

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.

What We Offer

Health & Wellness

• Medical, dental, and vision insurance*
• Health Savings Account (HSA) and/or Flexible Spending Account (FSA)*
• Employee Assistance Program (EAP)
• Wellness program and challenges
• Gym discounts

Financial Security

• 401(k) retirement plan with company match
• Life and disability insurance*
• Supplemental Critical Illness, Hospital Indemnity and Accident Insurance*
• Commuter benefits*

Time Off

• Paid time off (PTO) including vacation*, sick leave and holidays
• Parental leave
• Bereavement leave

Additional Perks

• Employee discounts
• Recognition programs
• Pet insurance*
• Available to eligible, full‑time employees only.

Illinois Hiring Range

$62,000—$70,000 USD

What We Offer

• Career Growth Opportunities
• Competitive Pay and Benefits
• Generous PTO and Parental Leave
• 401(K) Retirement Plan
• Life/ Disability Insurance
• Community Involvement
• Referral Bonuses and Product Discounts

Benefits vary by state, role type, and eligibility.

Follow us on Social Media

Instagram: @curaleaf.usa

Twitter: @Curaleaf_Inc

LinkedIn: Curaleaf LinkedIn

Curaleaf Holdings, Inc. (TSX: CURA) (OTCQX: CURLF) (“Curaleaf”) is a leading international provider of consumer products in cannabis with a mission to enhance lives by cultivating, sharing, and celebrating the power of the plant. As a high‑growth cannabis company known for quality, expertise and reliability, the Company, and its brands, including Curaleaf, Select, Grassroots, Find, and Anthem provide industry‑leading service, product selection and accessibility across the medical and adult‑use markets. Curaleaf International is powered by a strong presence in all stages of the supply chain. Its unique distribution network throughout Europe, Canada and Australasia brings together pioneering science and research with cutting‑edge cultivation, extraction and production.

Our Vision

To be the world’s leading cannabis company by consistently delivering superior products and services and driving the global acceptance of cannabis.

Our Values

• Lead and Inspire.
• Commit to Win.
• ONE Curaleaf.
• Driven to Deliver Excellence.

Curaleaf is an equal opportunity employer. Curaleaf recruits, employs, trains, compensates, and promotes regardless of race, religion, color, national origin, gender identity, sexual orientation, physical ability, age, veteran status, and other protected status as required by applicable law.

We will ensure that individuals with disabilities are provided reasonable accommodation to participate in the job application or interview process, to perform essential job functions, and to receive other benefits and privileges of employment. Please contact us to request accommodation.

Individuals adversely impacted by the war on drugs are encouraged to apply.

Current Curaleaf employees should apply for open positions through our Internal Job Board, which can be accessed via the link on The Leaf.

• Please note that U.S. immigration rules and regulations are governed by federal law; not state law. Although Curaleaf operates in states that have legalized and decriminalized marijuana, it is still considered a controlled substance under federal regulations and thus illegal under federal law. For this reason, unless and until federal law changes, Curaleaf is prohibited from offering sponsorship for any non‑immigrant or immigrant visas.
• Please also note that while candidates who are Lawful Permanent Residents (such as those with Green Cards) are eligible for employment with, and are hired by Curaleaf, working for a company engaged in a business that grows and sells a product that is illegal under federal law might compromise the candidate’s immigration status. Before a Lawful Permanent Resident accepts an offer of employment, Curaleaf recommends that the candidate seek the advice of an immigration lawyer.