Field Execution Senior Director

Title:Sr Director Field Execution - Wholesale

Location: Chicago, IL

Job Type:Full-Time | Travel 25-40%

About the Role:  The Sr. Director of Field Execution – Wholesale leads all direct engagement between Curaleaf brands, third-party dispensary partners, and their shoppers. As wholesale continues to evolve into a vital and dynamic growth channel, this role is central to accelerating brand presence and driving in-market relevance for the Curaleaf portfolio.

Leading a national field activation team across all U.S. sales regions, this senior leader brings to life high-impact brand programs—from trade shows and regional awareness campaigns to in-store activations that shape shopper behavior and strengthen brand loyalty.

We’re looking for a strategic, commercially minded marketing leader with exceptional field execution experience—someone who blends creativity with precision and thrives in fast-moving, highly regulated industries. You’ll navigate diverse markets, collaborate cross-functionally, and drive measurable results that move both the brand and business forward.

What You’ll Do: 

Regional Marketing Strategy & Execution

• Design and implement national and regional marketing programs aligned with sales and brand objectives.
• Translate brand strategies into actionable in-market activations across retail and event channels.
• Maximize regional budgets to ensure efficiency and reach.

Channel, Outlet & Event Activation

• Lead development of in-store programs, merchandising solutions, and point-of-sale materials.
• Partner with sales and wholesale teams to ensure consistent brand presence and flawless execution.
• Oversee local events, pop-ups, trade shows, and large-scale brand activations.

Cross-Functional Collaboration

• Serve as the key liaison between field sales and marketing teams.
• Collaborate closely with sales, brand, and compliance teams to align on regional and channel goals.
• Ensure programming supports both brand equity and commercial success.

Team Leadership & Development

• Lead, mentor, and grow a national team of field and trade marketing professionals.
• Foster a culture of accountability, creativity, and continuous improvement.
• Recruit and manage agency partners to ensure excellence in execution.

Promotions & Product Launches

• Develop and own the annual field activation calendar across regions and brands.
• Partner with brand and product teams to create impactful go-to-market strategies.
• Ensure retail readiness and sales enablement for all new product launches.

Customer Engagement & Brand Advocacy

• Develop and execute training programs for commercial teams and retail partners.
• Manage customer and budtender incentive programs to build engagement and brand love.
• Partner with influencers and local media to amplify brand presence and storytelling.

Compliance & Responsible Marketing

• Ensure all activations comply with state and federal regulations.
• Partner with Legal and Compliance on all claims, messaging, and event approvals.

What You’ll Bring:

• Bachelor’s degree in Marketing, Business Administration, or related field.
• 10+ years of experience in field marketing, brand activation, or trade marketing, including agency and team leadership.
• Proven track record of delivering breakthrough brand programs in retail and experiential environments.
• Strong understanding of sales and marketing alignment.
• Passion for the cannabis industry and its evolving consumer landscape.
• Highly organized and effective at managing multiple priorities across markets.
• Strategic and creative problem-solver with the ability to thrive in a regulated environment.
• Skilled at leveraging local media and digital platforms to drive engagement and conversion.

Even Better If:

• MBA or advanced degree.
• Experience in cannabis, alcohol, tobacco, pharma, or other regulated industries.
• Leadership experience within a shopper marketing or experiential agency.
• Expertise in influencer partnerships and localized media strategy.

Who You Are:

• A customer-obsessed marketer who understands how to connect brand and consumer at every touchpoint.
• A collaborative leader who inspires teams and drives accountability.
• A curious, creative, and adaptable problem-solver who thrives in ambiguity.
• A strategic thinker who also loves rolling up their sleeves to make big ideas happen.