Manager of Desktop Engineering

Information Technology Chicago, Illinois


Company: Oak Street Health 

Title: Manager, Desktop Engineering

Location: Chicago, Remote


Role Description:

Oak Street Health is seeking a Desktop Engineering Manager, to support day-to-day operations including scheduling, hiring, performance monitoring, and continual service improvement of endpoint services. You will oversee a team of endpoint engineers supporting the workstations.

The Desktop Engineering Manager should feel comfortable not only setting expectations for the team but also supporting the customer vision in deploying next-generation technology that drives imperative mission priorities. We are looking for someone who shows initiative, is self-directed, organized, and results-driven. The role will work as a mentor and teacher, working to identify skills gaps within the team and providing guidance and leadership to fill them through training and performance improvement.

Core Responsibilities:

  • Establish and document policies, practices, and working procedures needed for supported applications and services to deliver the intended results and for end users to make efficient and effective use of technology

  • Provide ongoing guidance concerning system usage and training

  • Participate and contribute to new Application and service evaluations

  • Collaborate with the Engineering, End User Support, and PMO teams to prioritize and plan project activities

  • Prepare comprehensive and well-structured proposals and plans to ensure that projects move successful completion

  • Coordination and management of the design, construction, deployment, and maintenance of personal computer operating system images, virtual desktops, and other application delivery platforms

  • Ongoing evaluation, selection, and effective use of deployment tools/systems

  • Coordinate with and manage a team to work with the appropriate Information Technology groups to ensure deployed systems and applications meet all firm user and client needs and requirements

  • Act as an Analyst/Consultant and provide systems and applications integration advice and expertise as needed throughout the firm and the department

  • Assist and guide the design and development of documentation and training materials to enable IT staff to use operating system and application deployment systems

  • Manage and participate in the design and implementation of software deployment packages and scripts to ensure timely and consistent deployment of new and updated software installations in a highly diverse user environment

  • Ensure control and coordination of the release management process for workstations

  • Ensure periodic audits of workstations occur to help ensure software licensing compliance

  • Further develop a Windows operations team responsible for directory services, patching, PC/service image design and deployment, and packaging services

  • Work Location – Hybrid, up to 3 days a week onsite.

  • Other duties as assigned

What are we looking for?

  • 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

  • Able to work under minimal supervision to complete projects and tasks on time

  • Able to work in high-pressure situations to find timely solutions

  • ITIL V4 Foundations certification

  • BA + 8 years of experience, AA + 12 years of experience, or 16 years of experience

  • 5 or more years of experience in a technical people management role

  • 8 or more years of hands-on experience in enterprise IT support

  • Experience managing engineers with varying skill levels and supporting end users remotely

  • Ability to provide rapid responses to all executive support requests and triage ongoing tickets

  • Working knowledge of Microsoft Windows Operating systems

  • Familiarity with Mobile Device Management application deployment technologies such as MS Intune

  • Familiarity to Microsoft M365 and Office 365 stack

  • Familiarity with standard Microsoft deployment tools and their application in the enterprise (Microsoft Deployment Toolkit/operating systems – Office Customization Tool/Microsoft Office suites and/or alternate third-party tools for deployment of core systems and applications

  • Demonstrated competency in one (or more) scripting languages (e.g., PowerShell)

  • Effective communicator at all levels, both written and verbal.

  • Experience with Patching and Endpoint Management Solutions (Intune, SCCM, BigFix, etc.)

  • Familiarity with Azure Virtual Desktop or other Virtual Desktop environments (VMWare, Citrix, etc.)

  • 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 delivering results

  • Being relentlessly determined

Why Oak Street Health?

Oak Street Health is on a mission to rebuild healthcare as it should be, providing personalized primary care for older adults on Medicare, with the goal of keeping patients healthy and living life to the fullest. Our innovative care model is centered right in our patient communities, and focused on the quality of care over volume of services. We are an organization on the move! With over 200+ locations and an ambitious growth trajectory, Oak Street Health is attracting and cultivating team members who embody Oaky values and passion for our mission.

Oak Street Health Benefits: 

  • Mission-focused career impacting change and measurably improving health outcomes for medicare patients

  • Paid vacation, sick time, and investment/retirement 401K match options

  • Health insurance, vision, and dental benefits

  • Opportunities for leadership development and continuing education stipends

  • New centers and flexible work environments

  • Opportunities for high levels of responsibility and rapid advancement


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

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