Desktop Engineer I

Information Technology Chicago, Illinois


Company: Oak Street Health 

Title: Desktop Engineer, IT

Location: Chicagoland. Must report onsite.


Oak Street Health is a rapidly growing, innovative company of community-based healthcare centers delivering 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 patients’ communities, we can help keep them healthy and 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 across the nation. With an ambitious growth trajectory, Oak Street Health is attracting and cultivating team members who embody Oak Street values and are passionate about our mission to rebuild healthcare as it should be.

For more information, visit

Role Description:

The Desktop Engineer will provide front-line support services for all support issues submitted by Company Employees. Duties will include installing and configuring PC hardware and software, evaluating and integrating new products, resolving computing issues, installing and troubleshooting peripheral devices, and maintaining the department's computer inventory.

Core Responsibilities:

  • Analyze, diagnose and resolve complex desktop end user problems and suggest corrective solutions.

  • Prepare, maintain and uphold logging and reporting procedures and monitor desktop operations.

  • Design and architect infrastructure using latest technologies.

  • Execute road map complying with technology and best practices.

  • Execute plans and implement technical infrastructure projects to refresh supported systems.

  • Document processes and procedures for maintenance and support.

  • Determine and leverage best practices amongst Desktop Engineering staff.

  • Offer third level desktop support to end-users running Windows workstations and laptops.

  • Extend remote support for global users.

  • Analyze root cause problems and execute corrective action.

  • Coordinate with computer specialists to resolve technical problems.

  • Execute, document and maintain desktop security standards as per IT security policies.

  • Handle system administration of enterprise desktop asset management software tools.

  • Review and test deployment updates through SSCM or MDT.

  • Handle Quality Assurance testing and application configurations using manual and automated testing tools.

  • Other duties as assigned

What are we looking for?

We’re looking for motivated professionals with:

  • An ambitious self-starter

  • Strong desire to solve with automation and self-service

  • A very strong and efficient communicator and collaborator

  • Able to multi-task and excel in a fast-paced trading environment

  • A deep problem solver; able to think on your own and develop quick, sound solutions to complex problems

  • Work well under minimal supervision to complete projects and tasks on time

  • Phenomenal customer service skills

  • Flexible and positive attitude

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

  • BS Degree in Computer Engineering, Computer Science or related field/technical experience

  • Expert administration/engineering skills in Windows 10 OS technologies

  • Minimum of 3 years supporting Windows desktop/server operating systems and technologies including Active Directory, DNS and DHCP and group policies

  • Advanced knowledge in automating for Windows platforms leveraging PowerShell, ActiveBatch, and SCCM or MDT

  • Strong technical ability and outstanding troubleshooting skills

  • US work authorization

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