Senior Systems Administrator – Cresco Labs – Chicago, IL

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.


The primary responsibility for the Senior Systems Administrator is the configuration and deployment of the Pepperi Wholesale (B2B) Sales Order Management (SOM) system to all markets as their primary. Additionally, they will shadow the team as a secondary resource on that CRM system to ensure coverage across these areas. An ideal candidate will have a record of success in improving processes and adoption using Wholesale SOM systems and understands the core functions and processes of B2B sales. The Senior Systems Administrator will work closely with business leaders, department heads, and subject matter experts to identify develop and deploy new business processes including: Wholesale Sales, CRM and Customer Service. This role is part administrator, part solution architect and part analyst for the Pepperi SOM system as a primary responsibility and the Salesforce system as a secondary responsibility. Once the Pepperi and Salesforce rollouts are completed the Senior Systems Administrator is responsible for day-to-day configuration, support, maintenance and improvement of both platforms, with a primary focus on Pepperi SOM system. Additionally, this role will also perform similar ongoing development and configuration of the Salesforce system. Sales team members heavily use both Pepperi SOM and Salesforce systems to optimize opportunities with wholesale customers and both systems are mission critical for this work.


  • Be a key administrator and developer of Pepperi’s SaaS Wholesale B2B SOM system, which will have 100+ internal users today and thousands of B2B customers in direct B2B ecommerce self-service in the future
  • Be a back-up developer and administrator of the Salesforce implementation
  • Help improve the Wholesale B2B processes across all markets through system driven process improvements and efficiencies
  • As part of the Pepperi SOM and Salesforce implementation teams help prioritize user stories and provide direction on rollouts to implementation partners
  • Use pilot deployments to provide standard Pepperi and Salesforce functionality for smaller teams using iterative agile development
  • Work with the implementation partners and map out all the data sources and integration needed for Pepperi and Salesforce
  • Work with our change management and training teams to establish suitable processes to support change management, user training for ongoing rollouts
  • Once launched handle all basic administrative functions including user account maintenance, reports and dashboards, workflows and other routine tasks
  • Work independently with members of the user community to define and document development requirements
  • As part of Pepperi SOM team monitor and manage data feeds and other integrations
  • Coordinate the evaluation, scope, prioritization and completion of new development requests once we go live.
  • Assist in training of new users, and grow the Pepperi SOM and skill set across the organization
  • Effectively act as the liaison between our users, vendors and the Pepperi SOM and Salesforce developers


  • Minimum 5 years of experience as an administrator in either Pepperi or another B2B SOM system
  • Minimum 3 years of experience as a administrator
  • Core understanding of Wholesale B2B SOM systems and processes
  • Admin (ADM201 and ADM211) certified a plus
  • Sales Cloud certified a plus
  • Service Cloud, CPQ and Developer certifications preferred
  • Marketing Cloud experience a bonus
  • At least two full implementations of a Wholesale B2B SOM
  • Experience driving change management and user adoption of Wholesale B2B SOM systems
  • Strong understanding of the Wholesale B2B SOM and Salesforce platforms, the various clouds, their interaction and the best way to implement and use them.
  • Ability to build custom apps and objects, formula fields, workflows, custom views, and other content of intermediate complexity
  • Understanding of declarative capabilities
  • Strong data management abilities
  • A documented history of successfully driving projects to completion
  • A demonstrated ability to understand and articulate complex IT landscapes with multiple systems
  • Previous experience working in a SCRUM or agile environment preferred


  • 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.

Apply Here

Share on facebook
Share on twitter
Share on reddit
Share on pinterest
Share on email

Scroll to Top