Windows System Engineer

Green Thumb Industries

Chicago, IL, USA

Full time

Sep 13

The Role 

The Windows System Engineer is responsible for building out, maintaining, and troubleshooting our rapidly expanding infrastructure.  As the Windows expert on our team, you will serve as the Subject Matter Expert around Active Directory and work to maintain our directory services as well as securely integrate with our enterprise applications and services. This role will also be responsible for providing superb technical competency, delivering mission critical infrastructure, and ensuring high levels of availability to support operations in retail, cultivation/production, and back office/HQ facilities.  


Interfaces with IT Operations team members to identify, analyze and resolve inefficient processes or standardizations across systems. 

Identify and implement areas of improvement in architecture 

Identify and implement, in conjunction with management and architects, areas for improvement within team with efficient and cutting-edge administration tools 

Building and implementing new or existing customer Microsoft environments. 

Handling Process & Automation Improvement projects, both Infrastructure and team-based initiatives. 

Performing and documenting disaster recovery tests 

Microsoft server-side support tickets through our ticket queue system that have gone through our Help Desk and NOC support 1-3 tiers 

Implementation and administration of Microsoft Windows Server 

Implementation and administration of Microsoft Exchange OnPrem and Office365 

Implementation and administration of Microsoft Active Directory environments 

Implementation and administration of Microsoft Azure environments as well as working in AWS 

Troubleshooting and maintenance of all above mentioned Microsoft Enterprise level products 

Knowledge and troubleshooting capability with multiple high availability solutions 

Continuous proactive maintenance, auditing, and monitoring of our customers Microsoft environments 

Following thorough Change Management processes and documentation 

Following thorough Root Cause Analysis processes and documentation 

Working with other infrastructure teams as well as non-infrastructure teams throughout organization on tasks 

Implementing server hardening/security best practices 

Server performance/capacity planning 

Troubleshooting supported end user application server issues 

Responsible for all tuning, monitoring and performance recommendations of the Microsoft systems 

Thorough environment documentation 

Ensures the efficient operation of daily activities and continuous improvement and automation of products and processes. 

Automates tasks by creating scripts in common scripting languages. 


Bachelor's degree in Computer Science, Information Management or a related field preferred 

4+ years' experience building Windows Server architecture using virtualization, cloud, and open-source technologies 

Knowledge of System Center Configuration Manager (SCCM) hierarchy, or similar tools, including administration, setup, configuration, troubleshooting, and maintenance 

Strong grasp of cloud-technology including Azure and AWS experience 

Solid knowledge of ITIL practices and demonstrated experience increasing ITIL capability 

Exceptional organization and planning skills and process-driven thinking 

Self-starter, creative, enthusiastic, innovative and collaborative outlook. 

Highly motivated, self-directed, innovative and able to work independently or among teams with keen judgement, common sense and resourcefulness 

Adapts and thrives in a demanding, fast-paced environment 

Possesses a high level of critical thinking 

Operates with a high level of professionalism and integrity, including dealing with confidential information 

 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

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Green Thumb Industries

Green Thumb | Health, Happiness & Wellbeing with Cannabis.