Senior Director, Digital; Retail

Overview

Join to apply for the Senior Director, Digital role at Cresco Labs.

Cresco Labs is one of the largest public, vertically integrated, multistate operators in the cannabis industry. Our portfolio includes in-house cultivated and manufactured brands with high-quality, award-winning products. With dozens of locations nationwide, our Sunnyside dispensaries provide a welcoming, judgment-free place to shop for anyone on their cannabis journey.

Founded in 2013, Cresco Labs aims to normalize and professionalize cannabis through our passionate employees, with a focus on Social Equity and Educational Development through our SEED initiative to reflect the communities we serve.

Our mission is to lead the nation’s cannabis industry with a focus on quality, consistency, integrity, and professionalism.

Cresco Labs is seeking a strategic and execution-oriented Sr. Director, Digital to own the full digital commerce ecosystem—from e-commerce and media to CRM, loyalty and analytics—ensuring seamless integration between online and in-store experiences. This role reports to the VP of Retail Operations and acts as the architect of a unified, data-driven customer ecosystem spanning paid, owned and earned channels. The ideal candidate will have experience building integrated digital strategies that drive customer acquisition, retention and lifetime value, while enhancing the overall digital customer journey.

The role requires a retail-first and digital-first thinker with ownership, follow-through, and operational excellence in a dynamic, high-growth environment.

• Owns the digital revenue contribution, site conversion and online-to-offline experience
• Manages and optimizes a multi-channel digital budget, directly accountable for ROI, ROAS and contribution margin
• Drives digital innovation from loyalty gamification and mobile app engagement to frictionless payments and emerging tech integration
• Partners with P&L owners to align digital marketing strategy and spend and translate goals into clear business outcomes
• Implements a test-and-learn culture leveraging A/B testing, predictive analytics and personalization to improve conversion and retention
• Defines and executes the digital product roadmap for retail marketing, collaborating with product and engineering teams
• Owns the development and performance of CRM channels, including personalized email and SMS marketing
• Drives paid media and national advertising, scalable outreach, referral and review programs
• Builds and mentors a growing digital team and fosters ownership, experimentation and innovation
• Partners with Regional VP of Retail to execute regional programs that drive consistency and adoption of marketing processes
• Provides dotted-line leadership to a regional marketing team for day-to-day execution and cross-functional alignment
• Establishes a culture of accountability and ownership within the digital marketing team
• Collaborates with Retail Operations, Merchandising & Planning, IT/Dev, Finance, HR, Wholesale Marketing to ensure unified execution
• Owns internal marketing operations systems and toolkits to ensure scalable, repeatable processes

• A bachelor’s degree and 10+ years of digital marketing experience in high-growth, multi-unit retail environments; cannabis experience is a plus but not required
• Best suited for someone who is Chicago-based and can participate in a hybrid work environment (office in Fulton Market 2-3 days per week). Quarterly travel in market
• Proven success in leading end-to-end digital commerce ecosystems that integrate loyalty, CRM, e-commerce, media and analytics
• Deep understanding of customer segmentation and lifecycle marketing, with demonstrated ability to personalize experiences that drive measurable outcomes
• Direct experience partnering with technology and data teams to build and optimize digital infrastructure and martech systems
• Experience assessing and integrating M&A opportunities 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)
• Ou…