Top Remote IT Jobs in Chicago, IL

Lead and execute remote technical implementations for dental practices from signing through go-live. Configure PMS integrations, set up remote access and network configurations, manage AWS-hosted Windows VMs/ETL, handle support volume, liaise with MSPs, and improve onboarding processes and automation while partnering with cross-functional teams.

Provide front-line technical support and customer service via phone and ticketing (ConnectWise). Troubleshoot hardware/software (Windows, macOS, MS Office), escalate as needed, document resolutions, perform occasional onsite visits, and meet service desk performance metrics.

Contract IT System Administrator to manage and harden multi-cloud (AWS/Azure) infrastructure and Microsoft 365 identity/collaboration stack, support endpoints and managed IT/security SaaS platforms, automate routine tasks with scripting, maintain documentation and compliance posture for Department of War mission spaces, and serve as hands-on technical escalation for operational issues.

Contract IT System Administrator to manage and harden multi-cloud (AWS/Azure) infrastructure and Microsoft 365/Entra ID, support endpoints and managed IT/security SaaS, automate admin tasks with scripting, maintain documentation, and help meet DoW security and compliance expectations.

Provide internal IT support and endpoint management for a fully remote workforce: provision and maintain macOS/Windows devices, enforce endpoint security, manage MDM/UEM and SaaS provisioning (Google Workspace, Slack, Atlassian), triage help desk tickets, maintain IT documentation, oversee vendor/licensing relationships, and partner on internal infrastructure and policy initiatives including AI tool governance.

Own and automate IT workflows and SaaS integrations (identity, collaboration, core business apps). Configure SSO and identity protocols, maintain DNS and email security, troubleshoot endpoints and apps, support SOC 2/SOX compliance, document standards, and partner cross-functionally to scale reliable, secure IT systems.

Provide on-site IT support and daily management of company information systems. Install, configure, upgrade, migrate, and troubleshoot PCs, laptops, cell phones, servers, printers, and voicemail. Administer user accounts, security, backups and archiving. Maintain inventory and documentation, liaise with vendors, assist corporate IT with projects, capacity planning, and disaster recovery. Serve as primary help-desk contact for local and remote users.

Provide live technical support for Maggie court reporting product: triage and resolve product, hardware, network, and audio issues via tickets, calls, and chats; coordinate escalations to IT and engineering; file bug reports; maintain knowledge base; take on-call shifts for P0 incidents; build runbooks and hardware kits.

Lead IT operations for a multi-site ambulatory surgery network, managing infrastructure, clinical and business systems, security and compliance, service desk, vendor relationships, and IT budgeting. Ensure uptime, drive integrations and migrations, execute DR/BC plans, and report operational metrics while partnering with the CIO on strategy and roadmaps.

Provide Tier 1 and Tier 2 IT support for a remote workforce: troubleshoot hardware, macOS, software, identity and SaaS issues; manage onboarding/offboarding, user access (SSO/MFA), device provisioning, asset inventory, and SaaS administration; create documentation; support IT projects and process improvements to enhance employee experience and security.

Design and produce a multi-module workshop series on Agentic AI for IT Support and Data Analytics: create lesson plans, scripts, demos, and 5–8 minute on-camera videos; build 30–45 minute hands-on workshops and performance-based assessments; translate real job tasks into progressive learning aligned to entry-level roles.

Serve as the primary on-site IT contact for the NYC office, resolving AV, network, hardware, and access issues via Jira Service Management. Manage device logistics and inventory, ensure timely laptop delivery, handle asset returns and e-waste, participate in sprint planning, escalate SEV1s, keep documentation current, and drive process improvements to elevate the employee IT experience.

Lead Net at Work's internal IT organization, ensuring reliability, security, scalability, and performance across applications, infrastructure, cloud, and cybersecurity. Oversee application rollouts, SDLC practices, operations, vendor relationships, budgeting, and acquisition due diligence. Partner with executives and business leaders to align technology roadmaps, governance, and service delivery while building a service-oriented, high-performing IT team.

Provide on-site (NYC) and remote end-user IT support: troubleshoot Windows/macOS/mobile devices, manage accounts in Azure AD/Active Directory, handle tickets, configure hardware and conferencing, use MSP tools, maintain documentation, and escalate complex issues.

Provide 2nd/3rd shift IT support for a remote workforce, focusing on macOS and Apple device troubleshooting, Google Workspace and Okta administration, MDM and asset management, ticketing, documentation, AI-enabled workflow automation, and collaboration with IT/security for endpoint hygiene and incident escalation.

Provide hands-on end-user IT support: troubleshoot OS/software, respond to tickets, apply patches, manage user accounts via Okta, configure MDM-managed mobile devices, and support Slack and Google Workspace integrations.

Execute testing, monitoring, and operational activities for IT controls across Project Management, Service Delivery, and SDLC. Provide guidance on control effectiveness, analyze data, document findings, support change management, and collaborate with stakeholders to ensure compliance and continuous improvement.

Provide onboard IT systems support, maintenance, monitoring, backups, inventory, hardware shipping/receiving, equipment repairs, user support and training, and escalate issues to the IT Officer while maintaining security and service standards.

Provide technical support and troubleshooting for IT systems, respond to user incidents, monitor system health, escalate complex issues, document resolutions, and assist with system maintenance and deployments.

Manage multi-site IT support operations for a manufacturing organization: lead L1/L2 teams, resolve hardware/software issues, oversee infrastructure, enforce cybersecurity, coordinate vendors, manage imaging and deployments, document systems, and align IT with production goals.

Provide front-line IT service desk support for global employees: triage and resolve tickets, manage Okta and Google Workspace lifecycles, deploy and troubleshoot macOS and mobile devices via Jamf, support VPN/Cloudflare One remote access, use AI tools to automate workflows, assist onboarding/offboarding, and train employees on technologies.

Hands-on individual contributor managing macOS and Windows endpoints, enforcing CIS controls with Jamf and Intune, scripting Automox Worklets (Bash/PowerShell), automating identity and SaaS provisioning, administering AWS/Azure IAM, owning help desk tickets (L1/L2), and driving workflow automation and continuous improvements.

Provide frontline and advanced application support for radiology imaging workflows: incident triage, user provisioning, configuration changes, DICOM troubleshooting, monitoring interfaces, coordinating with networks/storage/vendors, maintaining SOPs and knowledge base, delivering end‑user training and on‑call doctor support to meet SLAs.

Manage company devices, provisioning, lifecycle, and SaaS accounts; administer SharePoint and shared drives; implement IT security (MFA, endpoint controls); provide day-to-day support; coordinate vendors; develop IT policies, SOPs, and automation to scale internal IT operations.

Manage and improve cloud-based SaaS IT environment, administer M365 and identity systems, operate and tune security platforms (Arctic Wolf, Zscaler, Okta, Mimecast), monitor alerts and lead incident response, oversee helpdesk (Freshservice), manage vendors, enable users through training and documentation, and apply AI and automation to streamline IT operations.