Windows 11 Migration Jobs (NOW HIRING)

Sentinel is seeking an IT Systems and Infrastructure Manager for a Chicago-based partner. This role leads execution across cybersecurity, infrastructure, endpoint management, and enterprise IT operations. Responsibilities include driving initiatives such as email security, Intune/Autopilot deployments, Windows 11 migration, and incident response readiness, while ensuring network reliability, outage recovery, and failover planning. The manager partners with key vendors and oversees identity management, onboarding/offboarding, and cross-functional support across office, plant, and executive teams. Additionally, the role promotes continuous improvement through automation, documentation, user training, and standardized processes, while monitoring operational performance and high-volume support. This position ensures secure, scalable, and efficient IT operations aligned with business goals.

This is a contract-to-hire hybrid position that requires onsite work 4 of 5 days a week at the client location in Chicago, IL.

• Strong expertise in cybersecurity, email security, and compliance frameworks
• Deep knowledge of Microsoft 365, Intune, Autopilot, and Windows endpoint management
• Proven ability to manage network infrastructure, incident response, and outage recovery
• Experience supporting enterprise environments across office, plant, and executive functions
• Proficiency in identity and access management (Active Directory, MFA, user lifecycle)
• Ability to lead vendor relationships and coordinate with external partners (e.g., Cisco, AT&T, Sentinel)
• Strong process improvement mindset, including automation, documentation, and standardization.
• Excellent troubleshooting skills with capacity to manage high-volume IT support operations.
• Relevant IT certifications (e.g., Microsoft, Cisco, CompTIA, or cybersecurity-focused credentials) preferred
• Demonstrated experience in IT roadmap development and execution to support organizational growth and scalability
• A valid driver's license and proof of vehicle insurance will be required
• Legally authorized to work in the US without sponsorship
• Must demonstrate a "can-do" attitude

We focus on candidates that display our "ACE" factor - Attitude, Compassion, and Enthusiasm to deliver quality solutions with exceptional customer service.

Compensation Range: 

$90,000-$125,000

What you get:

We offer weekly competitive pay, medical, dental, vision, 401K and more.

MOTIVATED.....make IT happen!

Sentinel Technologies, Inc. has been rated a top workplace every year since 2012!

About Us:      

Sentinel delivers solutions that can efficiently address a range of IT needs - from security, to communications, to systems & networks, to software applications, to cloud and managed services; all of which include our staffing solutions for our clients. Since 1982, Sentinel has grown from providing technology maintenance services to our current standing as one of the leading IT services and solutions provider in the US. We have aligned with many of today's global technology leaders including Cisco, Dell, VMware and Microsoft. Sentinel services customers both nationally and internationally with primary support operating centers in Downers Grove (HQ), Chicago, and Springfield, IL; Phoenix, AZ.; Lansing, and Grand Rapids, MI; Milwaukee, WI; and Denver, CO.

If you are MOTIVATED... you can make IT happen at Sentinel. Our commitment to our employees is to create a work environment that encourages creativity, an entrepreneurial spirit, fosters growth through certification and hands-on training, and values a team-oriented culture with rewards based on impact!

If you share our passion about what technology can do and want to be part of a top workplace environment - we'd like to have you join our team.  Learn more at www.sentinel.com/careers.

As part of Sentinel's employment process, candidates will be required to complete a background check. Only those who meet the minimum requirements will be contacted. No phone calls please.

Sentinel is proud to be an equal opportunity employer including disability and veterans. In accordance with Title VII and state regulations, all qualified applicants will receive consideration for employment without regard to race, color, religion, age, sex, sexual orientation, gender identity, national origin, marital status, pregnancy, genetics, disability, military, veteran status or any other basis protected by law.

If you are an individual with a disability and need assistance in applying for a position, please contact SentinelHR1@sentinel.com.

The "Know Your Rights" Poster is available here

https://www.eeoc.gov/sites/default/files/2023-06/22-088_EEOC_KnowYourRights6.12ScreenRdr.pdf

Sentinel EEO Policy Statement is available here.

https://www.sentinel.com/about/diversity

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