Remote Windows Server Jobs in Chicago, IL (NOW HIRING)

The Systems Administrator will maintain, configure, and secure the organization’s Windows and Linux server/workstation infrastructure, with primary responsibilities in Active Directory (including Group Policy), PostgreSQL administration, Remote Desktop Services, and helpdesk assistance. Systems operate 24/7; the role requires flexibility for out-of-hours work and participation in an on-call rotation.

What You Get To Do…

• Administer Windows servers and workstations (installation, updates, troubleshooting, Windows Server features).
• Administer Linux servers (deployment, patching, package management, service monitoring, performance tuning).
• Administer Truenas (CORE and SCALE) file servers (management, service and performance)
• Install, configure, and maintain PostgreSQL databases: backups, replication, performance tuning, schema migrations, and troubleshooting.
• Manage Active Directory: user/group lifecycle, OU structure, Group Policy Object (GPO) design, application and troubleshooting, AD health monitoring.
• Configure and maintain Remote Desktop Services (RDS) / Terminal Services: session host farms, licensing, profiles, RD Gateway, and security.
• Provide first- and second-line helpdesk support for server- and workstation-related incidents; escalate to vendors or senior engineers as needed.
• Implement and maintain monitoring, logging, and alerting (metrics, log aggregation, capacity planning) to support 24/7 operations.
• Perform regular backups and validate disaster recovery and business continuity procedures for systems and databases.
• Harden systems and enforce security best practices: patch management, access controls, vulnerability remediation, auditing, and endpoint protection.
• Automate routine tasks and deployments using scripting (Bash, PowerShell, Python) and configuration management tools.
• Maintain accurate documentation: knowledgebase, on-call procedures, topology diagrams, change logs, and incident post-mortems.
• Participate in an on-call rotation and perform out-of-hours maintenance or incident response as required.

Requirements

• Bachelor’s degree in Computer Science, Information Technology, applicable performance experience and appropriate industry certifications are also acceptable.
• 3+ years of systems administration experience supporting both Linux and Windows environments.
• Strong Linux administration experience (e.g., Ubuntu, RedHat, and other distros).
• Solid Windows Server administration experience, including Active Directory and Group Policy.
• Experience administering Remote Desktop Services or equivalent VDI/session-host technologies.
• Practical PostgreSQL administration experience: backups, replication, tuning, maintenance, and troubleshooting.
• Experience providing helpdesk or end-user support and triaging incidents.
• Proficiency with scripting (Bash, PowerShell, Python) and familiarity with automation/configuration management tools.
• Knowledge of networking fundamentals (TCP/IP, DNS, DHCP, routing, firewalls).
• An understanding of security controls, IAM concepts, and best practices.
• Strong communication, documentation, and customer-service skills.

Bonus Points If You Have…

• Relevant certifications (RHCE/LPIC, Microsoft Certified: Azure/Windows Server, PostgreSQL certification).
• Experience with cloud platforms (AWS, Azure) and hybrid architectures (Entra, Intune).
• Familiarity with containerization (Docker) and orchestration (Kubernetes).
• Familiarity with virtualization platforms (Proxmox)
• Experience with remote profile management (FSLogix), session brokering, or VDI platforms.

Benefits

Econ One offers a competitive salary with an annual bonus and excellent benefits, which include employer-paid health, dental, life, and disability insurance, 401(k) plan with a generous employer match, Employee Stock Ownership Plan (ESOP) and flexible spending accounts.

To be considered for this position, please submit your application using the link provided in this job posting. Due to high volume of applications, we regret that we cannot respond to every candidate or to unsolicited messages sent via email or social media platforms such as LinkedIn. If you require any accommodations to complete your application, pleas contact us at hr@econone.com.

We are an Equal Opportunity Employer and value diversity at our company. All qualified applicants will receive consideration for employment without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, age, disability, veteran status, or any other protected characteristic under applicable law.

Notice to Recruitment Agencies

Econ One does not accept unsolicited resumes from external recruiters, staffing agencies, or search firms. Please do not forward resumes directly to our employees, hiring managers, or through our careers site. Unsolicited resumes will not be considered and will not create any obligation for the Company to pay a placement fee.