Retail Technology Operations Manager

@ Sunnyside*

Company Overview

Cresco Labs is one of the largest public, vertically integrated operators in the cannabis industry, featuring award-winning products and a commitment to social equity and educational development through our SEEDTM initiative. Our Sunnyside® dispensaries offer a welcoming, judgment-free environment for all customers.

Mission Statement

We aim to lead the nation’s cannabis industry with a focus on regulatory compliance, product consistency, and customer satisfaction, while acting with integrity and precision in every market.

Job Summary

The Retail Technology Operations Manager supports retail store technology deployments and roadmap as Cresco Labs expands. Reporting directly to the Director, Retail Technology, this role is based in Chicago, IL.

Core Job Duties

• Provide daily operations support for Sunnyside*.
• Utilize ITIL practices for asset management, service management, and change controls.
• Manage installations, upgrades, and configurations of hardware and software.
• Develop and document processes for technical issue resolution and client complaint handling.
• Maintain knowledge of technical policies regarding hardware use in dispensaries.
• Escalate technical issues per defined channels ensuring resolution quality.
• Collaborate with product owners to address root cause issues and document troubleshooting steps.
• Provide escalation guidance on technical and managerial operational issues.
• Ensure provision of technical equipment and support via internal ticketing systems (Freshservice) adhering to SLA standards.
• Achieve team KPIs on resolution time, response times, and end user satisfaction.

Sunnyside* Technology Solutions Implementation & Project Management

• Develop and deploy firmware, software, and hardware solutions.
• Plan, coordinate, and execute all technical components of projects.
• Collaborate with IT team members and contracted field service support.
• Provision hardware for dispensaries and support incident tracking and resolution.

Required Experience, Education and Skills

• Bachelor’s degree in IT Management, Information Systems, Business, or equivalent work experience.
• 3-5 years in IT hardware provisioning, logistics, or asset management.
• Strong analytical skills and business acumen with attention to detail.
• Professional communication skills with both technical and business teams.
• Ability to adapt to new technical and business environments.
• Experience in Digital Transformation and customer experience initiatives is a plus.
• Acquisition due diligence and integration experience is a plus.
• Physical requirements include standing 4 to 8 hours and lifting up to 50 lbs.
• Willingness to travel approximately 20% of the time.

Benefits

Cresco Labs offers robust benefits including major medical, dental and vision insurance, a 401(K)-match program, FSA/HSA, LTD/STD options, life insurance, AD&D, paid holidays, paid time off, annual bonuses, stock options, and an employee discount program.

Additional Requirements

• Must be 21 years or older.
• Compliance with legal and company regulations within the industry.
• Adherence to California Consumer Privacy Act guidelines for applicants.
• Awareness of fraudulent job offers and safe application practices.

Key skills/competency

Retail Technology Operations Manager, ITIL, Asset Management, Technical Support, Firmware, Software Deployment, Project Management, Troubleshooting, Digital Transformation, Customer Experience