Senior Associate, IT Server Administrator

Information Technology Chicago, Illinois


Company: Oak Street Health 

Title: Sr. Associate, IT Server Administrator 

Location: Downtown Chicago (30 W. Monroe St.)

Oak Street Health is a rapidly growing, innovative company of community-based healthcare centers that provides higher quality health and wellness care that improves outcomes, manages medical costs, and provides an unmatched experience for adults on Medicare in medically underserved communities.  By providing holistic, comprehensive and integrated care right in our patient’s communities, we can keep our patients healthy and then reinvest cost savings in further care for those same communities and others. Since 2013, Oak Street Health has brought its singular approach to tens of thousands of people in Illinois, Indiana, Michigan, Pennsylvania, and Ohio.  At 40 locations, and with an ambitious growth trajectory, Oak Street Health is attracting and cultivating team members who embody Oak Street values and are passionate about the mission to rebuild healthcare as it should be.

For more information, visit


Core Responsibilities:

Engineering and Provisioning

  • Engineering of related solutions for various project and operational needs.

  • Install new / rebuild existing servers and configure hardware, peripherals, services, settings, directories, storage, etc. in accordance with standards and project/operational requirements.

  • Install and configure systems such as supports EMR infrastructure applications or Asset Management applications.

  • Develop and maintain installation and configuration procedures.

  • Contribute to and maintain system standards.

  • Research and recommend innovative, and where possible automated approaches for system administration tasks.  Identify approaches that leverage our resources and provide economies of scale.

Operations and Support

  • Perform daily system monitoring, verifying the integrity and availability of all hardware, server resources, systems and key processes, reviewing system and application logs, and verifying completion of scheduled jobs such as backups.

  • Perform regular security monitoring to identify any possible intrusions.

  • Perform daily backup operations, ensuring all required file systems and system data are successfully backed up to the appropriate media

  • Create, change, and delete user accounts per request.

  • Provide Tier III/other support per request from various constituencies.  Investigate and troubleshoot issues.

  • Repair and recover from hardware or software failures.  Coordinate and communicate with impacted constituencies.


  • Apply OS patches and upgrades on a regular basis and upgrade administrative tools and utilities. Configure / add new services as necessary.

  • Upgrade and configure system software that supports EMR infrastructure applications or Asset Management applications per project or operational needs.

  • Maintain operational, configuration, or other procedures.

  • Perform periodic performance reporting to support capacity planning.

  • Perform ongoing performance tuning, hardware upgrades, and resource optimization as required.  Configure CPU, memory, and disk partitions as required.

  • Maintain data center environmental and monitoring equipment.

  • Other duties, as assigned 

This position will report to the Director of IT Engineering. 

What are we looking for?

We’re looking for motivated, experienced professionals with:

  • At least 8+ years server admin experience

  • Experience working with a multiple OS (Server 2008r2, 2012r2, 2016, 2019)

  • Associate's Degree required, Bachelor's degree preferred

  • Understanding of any EMR system processes

  • IIS Experience

  • SQL experience (2008r2, 2012,2014,2016,2017)

  • Experience with: VMware VCenter 6.0 and higher, VMware VSan 6.0 knowledge, Citrix ADC experience, Crowdstrike, Tenable, Sumo logic, MCSE, MCSA preferred

  • Demonstrated PC skills (MS Office, Google docs)

  • Ability to research emerging technologies and make recommendations that benefit our business

  • Knowledge of data center environments, hosting services, networks, and software as a service (SaaS)

  • Ability to document server physical / logical, topology

  • US work authorization

  • Someone who embodies being “Oaky”

What does being “Oaky” look like?

  • Radiating positive energy

  • Assuming good intentions

  • Creating an unmatched patient experience

  • Driving clinical excellence

  • Taking ownership and driving for results

  • Being scrappy

What does being “Oaky” look like?

  • Radiating positive energy

  • Assuming good intentions

  • Creating an unmatched patient experience

  • Driving clinical excellence

  • Taking ownership and delivering results

  • Being scrappy


Why Oak Street?

Oak Street Health offers our coworkers the opportunity to be at the forefront of a revolution in healthcare, as well as:

  • Collaborative and energetic culture

  • Fast-paced and innovative environment

  • Competitive benefits including paid vacation and sick time, generous 401K match with immediate vesting, and health benefits

Oak Street Health is an equal opportunity employer. We embrace diversity and encourage all interested readers to apply to