Windows Systems Administrator

job summary:

We are seeking a hands-on Windows Systems Administrator to join our remote-first team, focused on deploying and supporting the application infrastructure for our global hosted products and services. This role is a strategic blend of infrastructure engineering, application support, and systems administration.

This position is ideal for a professional with a strong foundation in Windows Server, IIS, and SQL administration who has the ambition to transition their career into the cloud. You will work across our hosted environments, collaborating closely with DevOps and product teams to ensure our platforms remain secure, scalable, and performant for thousands of users worldwide.

location: Chicago, Illinois

job type: Permanent

salary: $85,000 - 95,000 per year

work hours: 8am to 5pm

education: Bachelors



responsibilities:

• Lead the delivery and testing of new application infrastructure environments.
• Implement customer-specific infrastructure and application change requests in alignment with business policies.
• Facilitate the deployment and testing of software updates, patches, and hotfixes.
• Identify and resolve complex infrastructure and application-layer issues to minimize downtime.
• Document technical fixes, internal processes, and system improvements to strengthen team knowledge sharing.
• Maintain environment alignment with rigorous security standards, including ISO27001 and PCI-DSS.

qualifications:

Minimum of 5 years of experience in systems administration or infrastructure support.

Bachelor's degree in Information Science or a related field

Hands-on experience with Windows Server administration.

Solid experience with IIS (Internet Information Services), SQL Server connectivity, and SMTP services.

Proficiency in Identity Management, SSO, and Federation configuration.

Strong understanding of DNS, VNETs, VPNs, proxies, and firewalls.

Confidence troubleshooting Active Directory and complex hybrid-cloud setups.

Ability to translate complex technical issues into clear language for non-technical stakeholders.

Relevant cloud administration experience or certifications (Azure preferred).

Exposure to Infrastructure as Code (IaC) using Terraform.

Experience with CI/CD tooling and deployment pipelines (e.g., GitHub Actions).

Familiarity with Agile methodologies and ticketing tools like Jira and Confluence.

Equal Opportunity Employer: Race, Color, Religion, Sex, Sexual Orientation, Gender Identity, National Origin, Age, Genetic Information, Disability, Protected Veteran Status, or any other legally protected group status.

At Randstad Digital, we welcome people of all abilities and want to ensure that our hiring and interview process meets the needs of all applicants. If you require a reasonable accommodation to make your application or interview experience a great one, please contact

Pay offered to a successful candidate will be based on several factors including the candidate's education, work experience, work location, specific job duties, certifications, etc. In addition, Randstad Digital offers a comprehensive benefits package, including: medical, prescription, dental, vision, AD&D, and life insurance offerings, short-term disability, and a 401K plan (all benefits are based on eligibility).

This posting is open for thirty (30) days.