Sunnyside · 2 months ago
Senior Director, Digital (Retail)
Chicago, Illinois, United States
Full-time
Hybrid
Director/Executive
$170K/yr - $190K/yr
10+ years expCresco Labs is a leading operator in the cannabis industry, known for its quality products and commitment to social equity. They are seeking a Senior Director of Digital to oversee the digital commerce ecosystem, focusing on integrating online and in-store experiences while enhancing customer acquisition and retention strategies.
ConsumerHealth CarePersonal HealthPsychologyWellness
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
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
Qualification
Required
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
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
Preferred
Experience assessing and integrating M&A opportunities is a plus but not required
Benefits
Major medical
Dental and vision insurance
A 401(K)-match program
FSA/HSA programs
LTD/STD options
Life insurance
AD&D
Paid holidays
Paid time off
Annual discretionary bonuses
Stock options
Participation in our employee discount program
Company
Sunnyside
Sunnyside provides healthier drinking habits and avoid the negative effects of alcohol
11-50 employees
Funding
Current Stage
Early StageTotal Funding
$14.6MKey Investors
Motley Fool VenturesUncork Capital
2023-11-15Series A· $11.5M
2022-05-26Seed
2021-01-28Seed· $3.1M
Leadership Team
Nick Allen
Founder & CEO
Recent News
2025-10-06
2025-05-17
Company data provided by crunchbase