Sunnyside

Senior Director, Digital (Retail)

Sunnyside

Chicago, Illinois • Full-Time 💰 $170,000-$190,000

Posted 1 weeks ago • 20 views

Job Description

Cresco Labs is seeking a strategic and execution-oriented Sr. Director, Digital to own the full digital commerce ecosystem, ensuring seamless integration between online and in-store experiences. 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. The ideal candidate will have experience leading performance-driven marketing organizations at the forefront of retail innovation and must be able to define a compelling vision and lead with clarity, structure, and accountability.

Key Responsibilities

  • 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

Requirements

  • A bachelor's degree and 10+ years of digital marketing experience in high-growth, multi-unit retail environments
  • 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
  • Strong analytical mindset and comfort with KPIs spanning both customer behavior and commercial metrics
  • 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

Benefits & Perks

  • Major medical, dental, and vision insurance
  • 401(K)-match program
  • FSA/HSA programs
  • LTD/STD options
  • Life insurance and AD&D
  • Paid holidays and paid time off
  • Annual discretionary bonuses
  • Stock options
  • Employee discount program

Job Details

Job Type

Full-Time

Category

Marketing

Required License

Cannabis Employee Permit

Company Size

1000+ employees

Remote Work

On-site

Pay Range

$170,000-$190,000

About Sunnyside

Sunnyside

Sunnyside

Cannabis Dispensary

Sunnyside is a premier cannabis dispensary brand operated by Cresco Labs, offering a curated selection of cannabis products across multiple states. Sunnyside dispensaries provide an elevated retail experience with knowledgeable staff, quality products, and a welcoming environment for both medical patients and adult-use customers.

Chicago, IL
1000+ employees employees
Founded in 2019
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