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We're on a mission to normalize, professionalize and revolutionize cannabis

Director of Legal Operations

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Recently named one of Entrepreneur magazine’s Top 100 Cannabis Leaders, Cresco Labs is one of the largest vertically-integrated multi-state cannabis operators in the United States. Cresco is built to become the most important company in the cannabis industry by combining the most strategic geographic footprint with one of the leading distribution platforms in North America. Employing a consumer-packaged goods (“CPG”) approach to cannabis, Cresco’s house of brands is designed to meet the needs of all consumer segments and includes some of the most recognized and trusted national brands including Cresco, Remedi and Mindy’s, a line of edibles created by James Beard Award-winning chef Mindy Segal. Sunnyside*, Cresco’s national dispensary brand is a wellness-focused retailer designed to build trust, education and convenience for both existing and new cannabis consumers. Recognizing that the cannabis industry is poised to become one of the leading job creators in the country, Cresco has launched the industry’s first national comprehensive Social Equity and Educational Development (SEED) initiative designed to ensure that all members of society have the skills, knowledge and opportunity to work in and own businesses in the cannabis industry.


At Cresco, we aim to lead the nation’s cannabis industry with a focus on regulatory compliance, product consistency, and customer satisfaction. Our operations bring legitimacy to the cannabis industry by acting with the highest level of integrity, strictly adhering to regulations, and promoting the clinical efficacy of cannabis. As Cresco grows, we will operate with the same level of professionalism and precision in each new market we move in to.


Cresco Labs is seeking an experienced Director of Legal Operations to optimize the Legal Department as a business unit by implementing processes, practices, and systems to improve the day-to-day efficiency and effectiveness of the legal team, facilitate change, and control costs. This position will work very closely with the General Counsel and Legal leadership in an effort to manage business priorities and assist with executing the Legal Department’s operating model. The ideal candidate will have extensive hands-on experience directing administration and operations management within the legal department of a large, complex organization. This person will possess a strong business partner mindset and be able to expertly provide insight and guidance to the Cresco team. Many of the responsibilities will include driving operational planning, vendor management, assisting with budget development, financial planning and reconciliation, continuous improvement activities, and supporting special projects.


  • Define and drive strategic and operational initiatives with on-time and on-budget results
  • Develop and report on key operational and substantive metrics for the practice group that will better inform decision-making, including matter and work product analyses
  • Identify and implement legal department tools to streamline new or existing practices, as well as manage design, roll out, and training for new systems
  • Develop and enforce processes and policies to manage outside counsel usage and spend
  • Contribute to the development of common metrics to evaluate the efficiency of the Legal Department
  • Assist with the development and management of standard forms of agreements, documents, and policies
  • Assist Human Resources in managing legal department staffing (personnel budgeting and hiring)
  • Collaborate with the Finance Department to organize and manage the Legal Department’s budget and with other cross-functional teams to set objectives and achieve results
  • Utilize expertise in finance and consulting to manage billing, payment systems, and other Legal Department vendors
  • Organize Legal leadership meetings and manage subsequent action items
  • Integrate expert knowledge in eDiscovery, information governance, information technology, and information management principles, solutions, and best practices
  • Develop, implement, and lead technology platforms focused on cost and time efficiency, innovation, improving services, operational excellence, and effective data management
  • Develop and execute legal department resource planning and workflow optimization initiatives


  • Bachelor’s degree required; JD or MBA preferred
  • Minimum 6+ years’ of experience with legal operations and project management within a large, multi-site organization
  • Demonstrated experience building, running, and managing Legal programs, projects, and processes
  • Demonstrated ability to independently move projects forward by gaining support needed from others and to work collaboratively with cross-functional groups to set objectives, drive progress, and produce meaningful results
  • Strong experience in technology change management, project management, business process management, and system implementation
  • Strong analytical skills and ability to think through critical information, make informed recommendations, and problem-solve
  • Advanced proficiency in MS Excel, MS Office, and Adobe Suite required
  • Excellent organization and planning skills
  • Excellent people and communication skills (verbal and written)
  • Ability to work independently and successfully manage a high-volume workload with tight deadlines
  • Ability to model Cresco’s Values: Stewardship, Ownership, and Leadership


  • Must be 21 years of age or older to apply
  • Must comply with all legal or company regulations for working in the industry

Cresco Labs is an Equal Opportunity Employer and all applicants will be considered without attention to race, color, religion, sex, sexual orientation, gender identity, national origin, veteran, or disability status.


Cresco Labs at a glance

We're on a mission to normalize, professionalize and revolutionize cannabis

Cresco Labs focuses on Healthcare, Medical, Pharmaceuticals, Consumer Goods, and Canada. Their company has offices in Chicago. They have a large team that's between 501-1000 employees. To date, Cresco Labs has raised $415.5M of funding; their latest round was closed on February 2020.

You can view their website at or find them on Twitter, Facebook, and LinkedIn.

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