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Remote Level 2 It Support Jobs in Chicago, IL (NOW HIRING)

Sterling Engineering Inc.

Director of IT

Chicago, IL · On-site +1

Title : Director of IT - (Manufacturing and Industrial) Infrastructure and Delivery Location ... remote users. * Partner with operational technology teams to support secure IT/OT integration ...

Sentinel

IT Security Engineer

Downers Grove, IL · On-site +1

$70K - $100K/yr

The Sentinel IT Security Engineer will be responsible for supporting, administering ... This position can work remote within the United States and occasional travel to Downers Grove, IL ...

Sentinel

IT Security Engineer

Downers Grove, IL · On-site +1

$70K - $100K/yr

Responsibilities The Sentinel IT Security Engineer will be responsible for supporting ... This position can work remote within the United States and occasional travel to Downers Grove, IL ...

Sentinel

IT Security Engineer

Downers Grove, IL · On-site +1

$70K - $100K/yr

Responsibilities The Sentinel IT Security Engineer will be responsible for supporting ... This position can work remote within the United States and occasional travel to Downers Grove, IL ...

Natus Medical Incorporated

IT Director

Schaumburg, IL · On-site +1

TSA to support business growth. * Risk Management: Identify, assess, and mitigate risks related to ... Bachelor's Degree or an equivalent level of education and experience in IT, Computer Science ...

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All JobsLevel 2 It Support JobsRemote Level 2 It Support JobsRemote Level 2 It Support Jobs in Chicago, IL

Remote Level 2 It Support information

See Chicago, IL salary details

$15

$28

$46

How much do remote level 2 it support jobs pay per hour?

As of Aug 24, 2026, the average hourly pay for remote level 2 it support in Chicago, IL is $28.90, according to ZipRecruiter salary data. Most workers in this role earn between $23.03 and $32.45 per hour, depending on experience, location, and employer.

What is a remote level 2 IT support?

Remote Level 2 IT Support professionals provide technical assistance to users by resolving more complex IT issues that cannot be solved by Level 1 support. They work remotely to troubleshoot software, hardware, and network problems, often using remote access tools and advanced diagnostic methods. These specialists may also escalate unresolved issues to higher-level engineers, maintain documentation, and contribute to system improvements. Strong communication skills and in-depth technical knowledge are essential for this role.

What skills and qualifications are needed for remote level 2 IT support?

To excel as a Remote Level 2 IT Support specialist, you need advanced troubleshooting skills, strong knowledge of operating systems and networks, and usually a relevant IT degree or certifications like CompTIA A+ or Microsoft Certified: Windows Support. Familiarity with remote desktop tools, ticketing systems, and diagnostic utilities is essential for resolving complex user issues. Outstanding communication, patience, and problem-solving abilities help build trust and efficiently assist users remotely. These competencies ensure timely resolution of technical problems, minimize downtime, and maintain high levels of user satisfaction in a distributed work environment.

What challenges do remote level 2 IT support professionals face and how can they address them?

Remote Level 2 IT Support professionals often encounter challenges such as troubleshooting complex technical issues without physical access to devices, managing multiple support tickets simultaneously, and communicating clearly with end-users who may have varying levels of technical knowledge. To address these challenges, it's important to leverage remote diagnostic tools, maintain organized ticket management, and develop strong communication skills to guide users through solutions. Regular collaboration with Level 1 and Level 3 support teams also helps ensure escalated issues are resolved efficiently and knowledge is shared across the team.

What is the difference between Remote Level 2 It Support vs Remote Help Desk Technician?

AspectRemote Level 2 It SupportRemote Help Desk Technician
CertificationsCompTIA A+, Network+; Microsoft CertifiedCompTIA A+; Basic certifications
Work EnvironmentTechnical support, troubleshooting complex issuesCustomer support, basic troubleshooting
Employer UsageIT departments, managed service providersHelp desk services, IT support companies
Search IntentTechnical problem-solving, advanced supportBasic support, customer service

Remote Level 2 It Support involves handling more complex technical issues, requiring advanced certifications and troubleshooting skills. In contrast, Remote Help Desk Technicians focus on basic customer support and initial troubleshooting. Both roles are essential in IT support but differ in complexity and responsibilities.

What are the most commonly searched types of Level 2 It Support jobs in Chicago, IL?

The most popular types of Level 2 It Support jobs in Chicago, IL are:

What are popular job titles related to Remote Level 2 It Support jobs in Chicago, IL?

For Remote Level 2 It Support jobs in Chicago, IL, the most frequently searched job titles are:

What job categories do people searching Remote Level 2 It Support jobs in Chicago, IL look for?

The top searched job categories for Remote Level 2 It Support jobs in Chicago, IL are:

Remote Level 2 It Support jobs near you
Infographic showing various Remote Level 2 It Support job openings in Chicago, IL as of August 2026, with employment types broken down into 74% Full Time, 9% Part Time, and 17% Contract. Highlights an 100% Remote job distribution, with an average salary of $60,105 per year, or $28.9 per hour.

IT / Information Security Analyst II

Bloom Credit, Inc.

Chicago, IL • Remote

Full-time

Posted yesterday

New

Job description

IT / Information Security Analyst II

About the role

Bloom Credit is hiring an IT / Information Security Analyst II to own day-to-day IT operations and hands-on security work across a fully remote Mac fleet. This is a combined role: roughly 50/50 IT and IS in theory, with the mix shifting by project and business need.

You will work with strong support from the Head of IT/IS and partner across the entire organization—engineering, compliance, product, people ops, and other functions—as identity, devices, access, and security touch every team. You operate with high autonomy in a remote environment.

We maintain SOC 2 and PCI DSS (self-attested) obligations. Experience supporting audits and evidence collection is valued.

What you'll own (Analyst II)IT operations
  • Endpoint lifecycle for a remote Mac fleet (provisioning, configuration, support, offboarding)
  • Identity and access: JumpCloud directory / IdP / MDM, SSO app lifecycle, joiner–mover–leaver flows
  • Google Workspace administration (mail, groups, Drive, Meet) and related automation where useful
  • Helpdesk / end-user support: clear triage, resolution, and documentation
  • Asset lifecycle coordination (procurement, shipping, disposition) with existing tooling
  • Prefer native integrations and scripted automation over repetitive console click-ops; keep manual break-glass and validation paths documented
Information security
  • CrowdStrike EDR health, detections, containment, and response coordination
  • DLP controls and data-handling practices in daily ops, including policy tuning and exception handling
  • SIEM / security signal work in Datadog (alerting, investigation support, tuning with stakeholders)
  • Security hygiene: least privilege, access reviews, device posture, exception handling
  • Support SOC 2 and PCI evidence gathering with Compliance; keep controls operational, not theoretical
  • Zero Trust mindset preferred (identity-centric access, device trust, least privilege)—not required if you learn fast in this model
What you'll own (Analyst II)IT operations
  • Endpoint lifecycle for a remote Mac fleet (provisioning, configuration, support, offboarding)
  • Identity and access: JumpCloud directory / IdP / MDM, SSO app lifecycle, joiner–mover–leaver flows
  • Google Workspace administration (mail, groups, Drive, Meet) and related automation where useful
  • Helpdesk / end-user support: clear triage, resolution, and documentation
  • Asset lifecycle coordination (procurement, shipping, disposition) with existing tooling
  • Prefer native integrations and scripted automation over repetitive console click-ops; keep manual break-glass and validation paths documented
Information security
  • CrowdStrike EDR health, detections, containment, and response coordination
  • DLP controls and data-handling practices in daily ops, including policy tuning and exception handling
  • SIEM / security signal work in Datadog (alerting, investigation support, tuning with stakeholders)
  • Security hygiene: least privilege, access reviews, device posture, exception handling
  • Support SOC 2 and PCI evidence gathering with Compliance; keep controls operational, not theoretical
  • Zero Trust mindset preferred (identity-centric access, device trust, least privilege)—not required if you learn fast in this model
Education and credentials

No single path is required. Degrees, certifications, and on-the-job experience are weighed equally.

  • College - Associate's or bachelor's in IT, cybersecurity, CS, or related—or equivalent practical experience
  • Certifications - 1–2 relevant certs (e.g. Security+, Google Workspace Admin, JumpCloud, CrowdStrike, CySA+, GSEC) or equivalent demonstrated depth
  • On-the-job - ~4–6 years with ownership beyond ticket-only work; can run identity/endpoint/security ops with light oversight
How we work
  • Fully remote; no traditional office network—access is identity- and device-centric
  • Prefer native vendor integrations, then maintained scripts/automation, then console click-ops when that is the right business case
  • High-impact actions require clear scope, blast radius, and rollback thinking; Head of IT/IS approves before execution
  • Head of IT/IS available for support, escalation, and prioritization—not day-to-day micromanagement
Soft skills that matter here
  • Clear, concise written communication across the org
  • Calm triage under interruption (helpdesk + security signals)
  • Ownership of outcomes without waiting to be told
  • Collaborative posture—enable teams, don't gatekeep for its own sake