Senior Director, Digital (Retail)

JOB SUMMARY

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 individual will report directly to the VP of Retail Operations and serve as the key architect of a unified, data-driven customer ecosystem spanning paid, owned and earned channels. The role requires a retail-first and digital-first thinker with deep experience in building integrated digital strategies that drive customer acquisition, retention and lifetime value, while enhancing the overall digital customer journey. Success in this role demands someone who thrives in a dynamic, high-growth environment and approaches their work with ownership, follow-through, and operational excellence. The ideal candidate will have experience leading performance-driven marketing organizations at the forefront of retail innovation. They must be able to define a compelling vision and lead with clarity, structure, and accountability.

CORE JOB DUTIES

• 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 closely with P&L owners to align digital marketing strategy and spend, translating goals into clear business outcomes. Educates cross-functional stakeholders on the impact of digital marketing levers, driving understanding, trust, and shared accountability for results.
• 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 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.
• Builds and mentors a growing digital team, fostering a culture of ownership, experimentation and innovation.
• Partners with Regional VP of Retail to execute approved regional programs that drive consistency, performance, and adoption of marketing processes.
• Provides dotted-line leadership to a regional marketing team that supports day-to-day execution and cross-functional alignment across markets, ensuring consistency with national digital strategies.
• Establishes a culture of accountability and ownership within the digital marketing team, setting clear expectations and delivering results with operational excellence.
• Partners cross-functionally across Retail Operations, Merchandising & Planning, IT/Dev, Finance, HR, Wholesale Marketing etc. to ensure unified execution of initiatives and proactive communication of plans.
• Owns internal marketing operations systems and toolkits, ensuring processes are scalable, repeatable, and consistently executed across teams.

REQUIRED EXPERIENCE, EDUCATION AND SKILLS

• 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 our 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).
• 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.

BENEFITS

Cresco Labs is proud to offer eligible employees a robust offering of benefits including, major medical, dental and vision insurance, a 401(K)-match program, FSA/HSA programs, LTD/STD options, life insurance and AD&D. We also offer eligible employees paid holidays and paid time off. Other rewards may include annual discretionary bonuses, stock options as well as participation in our employee discount program. Benefits eligibility for permanent positions may vary by full-time or part-time roles, location, or position.