Vice President of Infrastructure and Enablement

Cresco Labs

Chicago, IL, USA

Full time

Jan 24

This job is no longer accepting applications.


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.


Reporting into the Chief Information Officer, the VP of Infrastructure and Enablement will lead a team across all systems and IT processes to support all business operations, including help desk, security, networks, applications, etc. Working closely with vendors and internal stakeholders of varying levels, the ideal candidate will be a deep technology practitioner with strong project management and budget analysis skills to prioritize and execute initiatives companywide.


Responsible for creating and implementing the Cresco Labs Playbook on building repeatable and sustainable solutions in a multi-cloud environment, including the support and enablement of the company’s Cloud Strategy for both AWS and Azure with a high caliber of expertise on Cloud architecture design, optimization and delivery

Drive strategic cloud operations and build Cloud Center of Excellence maturing management, operations, SLA’s and KPI’s for critical systems.

Ownership of network strategy and hardware deployment across a dispersed organization

Works with internal team and external partners to design, architect and deploy company LANs, WANs, and wireless networks, including virtual servers, routers, switches, UPSs, and other hardware.

Own the design, implementation, and support of firewalls, site-to-site VPNs, and remote-access VPNs

Works with internal and external teams to design and deploy all Physical Security software and hardware for the enterprise

Works closely with the SVP of IT Security to align infrastructure strategy with IT Security Program and support deployment of hardware and software assets to protect Cresco Labs

Owns and responsible for network configurations, health of network appliances and their connectivity to all other IT and infrastructural components, including outage management and recovery process.

Owns network asset management, including maintenance of network component inventory and related documentation and technical specifications information.

Directly interfaces with vendors, outsourcers, and contractors for price negotiations and procurement of network products and services.

Owns the Technology Helpdesk strategy and execution, defines Key Performance indicators for infrastructure team’s service delivery

Oversee installation, configuration, maintenance, and troubleshooting of end user workstation hardware, software, and peripheral devices, including asset lifecycle management.

Responsible for deep dive assessments when issues arise, put risk mitigation actions in place and impact analysis and design modifications to existing systems to support new solutions.

Collaborate with Crisis Management team to create the business continuity and disaster recovery program for Cresco Labs

Responsible for software asset management for critical Enterprise applications

Own all O365 collaboration and productivity tools deployment and support for the Enterprise

Responsible for Azure Active Directory backbone and Integrations with key systems across the enterprise

Works closely with various cross functional members to evaluate acquisition targets and give assessments on their infrastructure platform, leading infrastructure integrations and migration plans


Bachelor's degree in Computer Science, Information Systems or a related field required; Related Master’s degree, preferred

10+ years’ experience in a production IT environment managing enterprise IT infrastructure, hardware, hosting service and network areas.

5+ years of leadership experience, with a focus on building and scaling teams, must be comfortable mentoring and coaching of team members

Ability to prepare and manage to a departmental budget.

Comfortable presenting and communicating across the organization, including with C-Suite and Board level stakeholders

Ability to write and review architectural design documents

Knowledge and understanding of industry trends and new technologies and ability to apply trends in all areas including OS, network and Cloud technologies

Must have a thorough knowledge of the Windows OS, Azure Active Directory and its concepts, and the interaction between hardware, operating systems, network, and application software.

Experience managing and architecting components of cloud platforms and infrastructure, including AWS and Azure.

Experience with Linux, Unix, Service Now, Intune and Jamf is a plus

Ability to understand business drivers in order to organize and prioritize multiple competing deadlines and assigning resources accordingly

Strong communication, analytical and problem-solving skills with the ability to drive actionable changes


Cresco Labs requires that all corporate employees be fully vaccinated against the COVID-19 virus on or before September 30, 2021. If you are offered and accept a position, you will be required to prove your vaccination status prior to when your employment begins. If you require a medical or religious accommodation with regard to vaccination, please let us know once you receive an offer of employment (if applicable).


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.

You must be logged in to to apply to this job.


Your application has been successfully submitted.

Please fix the errors below and resubmit.

Something went wrong. Please try again later or contact us.

Personal Information


View resume


Cresco Labs

Normalize and professionalize cannabis and educate consumers to eliminate the social stigmas associated with cannabis