🔹 Job Title: VP, Retail Marketing
🔹 Company: Cresco Labs
🔹 Location: Chicago, Illinois
🔹 Job Type: Hybrid
🔹 Category: Alternative Medicine
🔹 Date Posted: July 14, 2025
🚀 Job Overview
- Strategic and execution-oriented role leading retail marketing for Sunnyside business
- Reports directly to SVP of Retail and serves as key architect of retail brand, digital experience, and shopper communications
- Requires retail-first and digital-first thinker with deep experience in building scalable marketing systems
- Success demands ownership, follow-through, and operational excellence
📋 Key Responsibilities
- Owns end-to-end marketing strategy for retail business, driving customer acquisition, retention, and brand affinity at scale
- Architects retail marketing budget, accountable for delivering measurable results accretive to the business
- Partners closely with P&L owners to align marketing strategy and spend, translating goals into clear business outcomes
- Sets and leads retail brand vision, positioning, and identity, ensuring cohesion across store design, visual merchandising, content, e-commerce, and Sunnyside owned brand
- Builds and scales marketing programs that can be executed with nuance locally and effectively implemented across stores in partnership with field operations and store teams
- Leads measurement and optimization of full-funnel marketing, from discovery through repeat visits, using structured KPIs to assess and drive impact
- Leads digital-first retail innovation, including loyalty programs, personalized e-commerce experiences, and frictionless transactions in-store and online
- Defines and executes digital product roadmap for retail marketing, collaborating with product and engineering teams to bring to life seamless customer journeys
- Owns the development and performance of CRM channels, including personalized, high-conversion email and SMS marketing
- Drives paid media and national advertising, scalable outreach, referral and review programs, building systems to convert satisfied customers into promoters and new traffic
- Leads in-house creative agency, delivering exceptional creative and production output on brief and on time, balancing the needs of high quality and high quantity work
- Provides dotted-line leadership to regional marketing team, ensuring continuity of brand expression and consistency with national commercial strategies
- Partners with Regional VP of Retail to execute approved regional programs that drive consistency, performance, and adoption of marketing processes
- Establishes a culture of accountability and ownership within the marketing team, setting clear expectations and delivering results with operational excellence
- Partners cross-functionally across Retail Operations, Merchandising & Planning, Dev, Finance, HR, Wholesale Marketing, etc. to ensure unified execution of initiatives and proactive communication of plans
- Champions a strong feedback and testing culture, leveraging performance data to continually iterate and improve marketing programs
- Owns internal marketing operations systems and toolkits, ensuring processes are scalable, repeatable, and consistently executed across teams
🎯 Required Qualifications
- Bachelor’s degree and 10+ years of marketing leadership experience in high-growth, multi-unit retail environments; cannabis experience is a plus but not required
- Chicago-based and can participate in hybrid work environment (office in Fulton Market 2-3 days per week); quarterly travel in market
- Proven success in leading digital and omnichannel retail marketing, including loyalty, e-commerce, CRM, and performance marketing
- Deep understanding of customer segmentation and lifecycle marketing, with demonstrated ability to personalize experiences that drive measurable outcomes
- Experience building and evolving brand systems across all physical and digital retail touchpoints, including store concept and design
- Demonstrated ability to define and lead digital product roadmaps in collaboration with cross-functional teams
- Experience assessing and integrating M&A is a plus but not required
- Strong analytical mindset and comfort with KPIs spanning both customer behavior and commercial metrics (e.g., CLV, NPS, frequency, retention, ATV, CAC, ROAS, loyalty engagement)
- Outstanding communication and stakeholder management skills, with a proactive and transparent approach to cross-functional collaboration
- A builder and leader of high-performing teams, who sets a high bar, offers strong support, and develops future leaders
- Operates with an ownership mindset — delivers with excellence, follows through on commitments, and proactively solves problems
💰 Compensation & Benefits
- Salary Range: $195,000 - $215,000 USD per year
- Benefits:
- Major Medical
- Dental Insurance
- Vision Insurance
- 401(K)-Match Program
- FSA/HSA Programs
- LTD/STD Options
- Life Insurance
- AD&D
- Paid Holidays
- Paid Time Off
- Annual Discretionary Bonuses
- Stock Options
- Employee Discount Program
📌 Applicant Insights
🔍 Company Context
- Industry: Alternative Medicine
- Company Size: 1,001-5,000 employees
- Founded: 2013
- Company Description: Cresco Labs is one of the largest public, vertically integrated, multistate operators in the cannabis industry. Our portfolio of in-house cultivated and manufactured brands features some of the highest quality, most awarded and most popular cannabis products in America. With dozens of locations nationwide, our owned and operated Sunnyside® dispensaries provide a welcoming, positive, judgement-free place to shop for anyone at any point on their cannabis journey. Founded in 2013, Cresco Labs’ mission is to normalize and professionalize cannabis through our passionate employees. As stewards of the cannabis industry, our teams are constantly focused on supporting the needs of our fellow colleagues, consumers, customers, and communities alike. With a focus on Social Equity and Educational Development, our SEED™ initiative ensures that our company reflects the communities in which we serve, ensuring equal opportunity for all to have the knowledge and resources to work in and own businesses in cannabis. At Cresco Labs, we aim to revolutionize and lead the nation’s cannabis industry with a focus on quality and consistency of product, and to bring legitimacy to the industry with the highest level of integrity and professionalism.
- Company Specialties: Cultivation, manufacturing, wholesale distribution, and retail
📊 Role Analysis
- Career Level: Executive
- Reporting Structure: Reports directly to SVP of Retail
- Work Arrangement: Hybrid (2-3 days per week in the office)
- Growth Opportunities:
- Potential to shape the retail marketing strategy for a rapidly growing cannabis company
- Opportunity to work cross-functionally with various teams to drive business growth
- Possibility to develop and mentor a regional marketing team
🌍 Location & Work Environment
- Office Type: Hybrid (Fulton Market, Chicago)
- Office Location(s): 600 W Fulton St, Chicago, Illinois 60661, US
- Geographic Context: Chicago, Illinois, United States
- Work Schedule: Full-time (40 hours per week)
💼 Interview & Application Insights
- Typical Process: Application review, phone/ video screen, on-site interview, final round interview
- Key Assessment Areas:
- Marketing strategy and execution
- Leadership and team management
- Analytical skills and data-driven decision making
- Cultural fit and alignment with company values
- Application Tips:
- Tailor your resume and cover letter to highlight relevant marketing experience and skills
- Prepare for behavioral interview questions focusing on leadership, problem-solving, and adaptability
- Research Cresco Labs and the cannabis industry to demonstrate your enthusiasm and understanding
🛠 Tools & Technologies
- Marketing automation tools (e.g., Marketo, HubSpot)
- CRM software (e.g., Salesforce, Zoho CRM)
- Email marketing platforms (e.g., Mailchimp, Constant Contact)
- Social media management tools (e.g., Hootsuite, Buffer)
- SEO and analytics tools (e.g., Google Analytics, SEMrush)
- Project management software (e.g., Asana, Trello)
- Design and creative tools (e.g., Adobe Creative Suite, Sketch)
👔 Cultural Fit Considerations
- Company Values: Integrity, Professionalism, Innovation, Collaboration, Empowerment, and Community
- Work Style: Fast-paced, dynamic, data-driven, and customer-focused
- Self-Assessment Questions:
- How do you align with Cresco Labs' commitment to normalizing and professionalizing cannabis?
- How do you approach working in a hybrid office environment?
- How do you ensure the consistency of brand expression across multiple channels and locations?
⚠️ Potential Challenges
- Navigating the complex and evolving cannabis industry regulations
- Managing a remote regional marketing team with limited resources
- Balancing the needs of high-quality and high-quantity creative work
- Ensuring consistent brand expression across various retail touchpoints and digital channels
📈 Similar Roles Comparison
- Differences from related positions: This role focuses on retail marketing for a cannabis company, requiring industry-specific knowledge and experience with cannabis regulations
- Industry-specific context: The cannabis industry is highly regulated and rapidly evolving, presenting unique challenges and opportunities
- Career path comparison: This role can serve as a stepping stone to senior marketing leadership positions within the cannabis industry or other highly regulated industries
📝 Sample Projects
- Developing and executing a customer acquisition campaign targeting new cannabis users
- Launching a loyalty program to drive repeat visits and customer retention
- Collaborating with product and engineering teams to enhance the e-commerce platform and improve user experience
💡 Key Questions to Ask During Interview
- What are the biggest challenges facing the retail marketing team currently, and how can this role help address them?
- How does Cresco Labs support the growth and development of its marketing team members?
- What are the key performance indicators (KPIs) used to measure the success of retail marketing campaigns, and how are they tracked and analyzed?
- How does Cresco Labs approach working with regulatory bodies and ensuring compliance with cannabis regulations?
📌 Next Steps for Applicants
- To apply for this position:
- Submit your application through [this link](https://job-boards.greenhouse.io/crescolabs/jobs/8071485002)
- Tailor your resume and cover letter to highlight relevant marketing experience and skills
- Prepare for behavioral interview questions focusing on leadership, problem-solving, and adaptability
- Research Cresco Labs and the cannabis industry to demonstrate your enthusiasm and understanding
- Follow up with the hiring manager after your interview to reiterate your interest in the position and address any concerns or questions
⚠️ Disclaimer
- This job description contains AI-assisted information. Details should be verified directly with the employer before making decisions.
