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Flex Chicago Tech Jobs (NOW HIRING)

Sierra ITS

Senior Support Specialist

Deerfield, IL · On-site

Familiarity with Flex workspace and modern office tech implementations. The right person will have ~5 years of experience doing the work, all in person and ready to start! Local (Chicago area ...

Simos

Warehouse Production Associate

IL · On-site

$16.60/hr

... client, Flex-N-Gate, the leading manufacturer and supplier of front-end components for the ... This warehouse position is located in the Hegewisch neighborhood in Chicago, IL. Available Shift:

KurzSolutions

Anesthesiologist

Chicago, IL

$412K/yr

... It plays a significant role in the air transportation network of the Chicago metropolitan area ... Completion of approved Residency in Anesthesia as per ECFMC and FLEX requirements. * Current ...

Fooda

Client Success Partner

Detroit, MI · On-site

$60K - $70K/yr

They had an idea: bring Chicago's local restaurant culture inside the office to sell food. It was ... Powered by technology and a network of 1500+ restaurants, we feed hungry people at work through a ...

Fooda

Client Success Partner

Tampa, FL · On-site

$60K - $70K/yr

They had an idea: bring Chicago's local restaurant culture inside the office to sell food. It was ... Powered by technology and a network of 1500+ restaurants, we feed hungry people at work through a ...

Fooda

Client Success Partner

Detroit, MI · On-site

They had an idea: bring Chicago's local restaurant culture inside the office to sell food. It was ... Powered by technology and a network of 1500+ restaurants, we feed hungry people at work through a ...

Fooda

Client Success Partner

Tampa, FL · On-site

They had an idea: bring Chicago's local restaurant culture inside the office to sell food. It was ... Powered by technology and a network of 1500+ restaurants, we feed hungry people at work through a ...

Fooda

Client Success Partner

Atlanta, GA

$60K - $70K/yr

They had an idea: bring Chicago's local restaurant culture inside the office to sell food. It was ... Powered by technology and a network of 1500+ restaurants, we feed hungry people at work through a ...

Fooda

Client Success Partner

Tampa, FL

$60K - $70K/yr

They had an idea: bring Chicago's local restaurant culture inside the office to sell food. It was ... Powered by technology and a network of 1500+ restaurants, we feed hungry people at work through a ...

Fooda

Client Success Partner

Atlanta, GA · On-site

$60K - $70K/yr

They had an idea: bring Chicago's local restaurant culture inside the office to sell food. It was ... Powered by technology and a network of 1500+ restaurants, we feed hungry people at work through a ...

Fooda

Client Success Partner

Atlanta, GA · On-site

They had an idea: bring Chicago's local restaurant culture inside the office to sell food. It was ... Powered by technology and a network of 1500+ restaurants, we feed hungry people at work through a ...

Fooda

Client Success Partner

Detroit, MI · On-site

$60K - $70K/yr

They had an idea: bring Chicago's local restaurant culture inside the office to sell food. It was ... Powered by technology and a network of 1500+ restaurants, we feed hungry people at work through a ...

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Flex Chicago Tech information

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$74.5K

$92.5K

$108K

How much do flex chicago tech jobs pay per year?

As of Jun 7, 2026, the average yearly pay for flex chicago tech in the United States is $92,500.00, according to ZipRecruiter salary data. Most workers in this role earn between $83,500.00 and $101,500.00 per year, depending on experience, location, and employer.

What is the difference between Flex Chicago Tech vs Network Technician?

AspectFlex Chicago TechNetwork Technician
CredentialsTypically requires technical certifications like CompTIA A+ or Network+Often requires similar certifications, sometimes Cisco CCNA
Work EnvironmentOn-site and remote support, troubleshooting hardware/software issuesPrimarily on-site network setup, maintenance, and troubleshooting
Industry UsageUsed across various industries including IT, healthcare, and retailPrimarily in IT and telecommunications sectors

Flex Chicago Tech and Network Technicians both require technical certifications and work in similar environments. However, Flex Chicago Tech roles often encompass broader IT support tasks, while Network Technicians focus specifically on network infrastructure. Both roles are essential in maintaining organizational technology systems.

What cities are hiring for Flex Chicago Tech jobs? Cities with the most Flex Chicago Tech job openings:
What are the most commonly searched types of Chicago Tech jobs? The most popular types of Chicago Tech jobs are:
What job categories do people searching Flex Chicago Tech jobs look for? The top searched job categories for Flex Chicago Tech jobs are:
Flex Chicago Tech jobs near you
Infographic showing various Flex Chicago Tech job openings in the United States as of May 2026, with employment types broken down into 50% Full Time, and 50% Part Time. Highlights an 100% In-person job distribution, with an average salary of $92,500 per year, or $44.5 per hour.
Senior Support Specialist

Senior Support Specialist

Sierra ITS

Deerfield, IL • On-site

Contractor

Posted 21 days ago

Job description

Job description

Overview:

We're looking for two experienced Senior IT Support Technicians to join our expanding IT team and play a critical role in scaling support for a rapidly growing organization. You'll be embedded at the HQ, working directly with executives, providing high-touch white-glove support, and helping lead key rollouts and infrastructure initiatives.

Responsibilities:

  • Primary point of contact for executive support-handle high-priority tickets and day-to-day tech needs for 30+ execs.
  • Provide 2nd and 3rd level support for Windows 10, Mac OS, Office 365, and enterprise collaboration tools.
  • Lead and support rollouts of new technologies and hardware across the org, including onboarding hundreds of new users.
  • Troubleshoot and support conference room tech: Cisco, Crestron, A/V setups, video conferencing hardware.
  • Implement and support infrastructure and security projects, such as modernizing video conferencing, flexible workspace tools, etc.
  • Support enterprise platforms: Box, Okta, Microsoft Teams, Office 365, Zoom, and MS Teams Voice.
  • Support executive communications and phones: MS Teams Phone, Cisco voice systems, and conference room integrations.
  • Assist in managing software deployment and license tracking using standard deployment tools and inventory systems.

Required Skills & Experience:

  • 5+ years in IT support, with 2+ years supporting executives.
  • Strong experience with Windows 10, Office 365, and Mac OS.
  • Experience with Crestron, Cisco conferencing, and troubleshooting A/V environments.
  • Proven ability to work independently, take initiative, and drive tech projects.
  • Familiarity with enterprise collaboration and identity management tools (Okta, Teams, Box, Zoom, etc.).
  • Customer-service mindset with clear communication and attention to detail.

Nice-to-Haves:

  • Experience in fast-growing or scaling organizations.
  • Certifications: Microsoft, Apple, Cisco, or ITIL.
  • Familiarity with Flex workspace and modern office tech implementations.

The right person will have ~5 years of experience doing the work, all in person and ready to start!

Local (Chicago area) applicants only, no third parties. To facilitate the process, email me directly at b p e n n e y @ s i e r r a i t s . c o m with "WHITE GLOVE) in the subject line. Thank you for reading!