Director, Commercial Strategy

Chicago, IL

The Director of Commercial Strategy is a high-visibility role responsible for helping to define and drive Green Thumb’s lofty ambitions. This individual will join our commercial leadership team to tackle and drive the most pressing strategic priorities across our business. This team and role will define, manage, and execute strategic initiatives to shape how we operate our business today and for years to come. 

This individual will have the opportunity to work on a broad variety of projects providing exposure to retail, sales, marketing, finance, and operations/cultivation functions, paving the way for future career opportunities throughout our organization. We expect that this role will help build a deep understanding of many facets of our business, and this individual would ideally then transition to a CGM (Commercial General Manager) role to lead a region and manage the P&L. 

Reporting into the Vice President, Commercial Strategy, Marketing, and Planning, this team and individual will have significant exposure to the executive leadership team and serve as the go-to partners for the C-Suite to address existing challenges and establish new strategies to grow our business. To drive results, this individual will bring a people-first approach to building a team and developing and implementing strategies across a range of topics such as regional growth strategies, business process improvement, and capability building. 

Strategy Development 

  • Partner with the executive and Revenue Org leadership teams to define priorities, identify the most pressing needs, and drive strategic initiatives to bring our priorities to life throughout the organization
  • Develop and refine commercial strategies for markets, channels, and strategic customers based on current landscape, regulatory frameworks, and future ambitions
  • Support evaluation of corporate performance and develop recommendations to improve effectiveness of our execution strategies
  • Develop presentations and cohesive storylines for the strategic initiatives, adapting each to the target audience (e.g., retail operations vs. sales team vs. executive leadership) 

Analysis, Insights and Organizational Effectiveness

  • Leverage data and insights to identify drivers of our business and model implications of changes based on strategic shifts and/or regulatory changes
  • Lead and/or collaborate on ad-hoc analysis on brand, category, channel, and market level performance to support strategic objectives and business goals
  • Evaluate the effectiveness of key strategic commercial and market initiatives with regular reporting to senior leadership
  • Identify, develop, and execute enhancements and expansion of our organizational processes and tools 

Stakeholder Management

  • Collaborate closely with cross-functional counterparts to develop plans that ensure quality of recommendations and successful outcomes
  • Support executive leadership in the development of messaging and presentations for key internal and external meetings
  • Collaborate closely with Finance and IT to enhance reporting and analytics systems 


  • Establish Commercial Strategy team as a go-to resource for high-quality strategic insight, analytics, and concise executive-level communication of business performance, opportunities, and strategies 
  • Build and develop supporting team over time as role and function are integrated into the business 


  • Education: Bachelors degree required, MBA preferred 
  • Experience: 4+ years of graduating experience in management consulting or corporate strategy role, CPG experience preferred
  • Industry Knowledge (Preferred): Understanding of the cannabis market and/or similar highly regulated industries (e.g. Beverage Alcohol, Tobacco, etc.)
  • Collaboration: Experience working within a highly matrixed function and partnering with various groups – sales, brand marketing, retail operations, etc.
  • Project/Process/Stakeholder Management: Proven ability to manage projects from start to finish, with a focus on managing stakeholders and proactively identifying differing perspectives to anticipate and address challenges and gaps
  • People Leadership: Experience managing project teams and coaching direct reports to drive outcomes and develop pipeline of talent for the broader organization
  • Presentation Effectiveness: Ability to translate insights into structured presentations that highlight key takeaways; Ability to present effectively to senior audiences
  • Advanced Analytics: Ability to identify, analyze, and interpret trends in complex data sets to inform decision making 

Additional Requirements 

  • Must pass any and all required background checks  
  • Must be and remain compliant with all legal or company regulations for working in the industry  
  • Must possess valid driver’s license 
  • Must be a minimum of 21 years of age 
  • Must be approved by state badging agency to work in cannabis industry

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