Creative Financial Staffing (CFS) is hiring: IT Support Specialist in Chicago

Overview

IT Support Specialist – Permanent/Part Time

Location: Chicago, IL. Environment: Hybrid. Hours per week: ~20. Local candidates only. No sponsorship available.

Compensation: $25,000 - $30,000 per year. ($50,000 - $60,000 if 40 hours/week)

Job Summary

This role requires flexibility to support both corporate offices and family households in person. The candidate should be willing and able to travel between office locations and family residences, as needed, to provide on-site support. While day-to-day responsibilities can often be coordinated remotely in partnership with the MSP, regular in-person presence at both office locations (ideally one day per week at each) is required to build relationships, address issues proactively, and provide hands-on support. Additional visits to family residences or offices may be required from time to time for projects, troubleshooting, or urgent support needs. Willingness to provide after-hours support and respond to urgent issues on an as-needed basis is critical.

Job Responsibilities

• Provide direct, hands-on support to family members for home and personal technology.
• Troubleshoot and resolve issues with home Wi-Fi networks, personal laptops, mobile devices, printers, smart-home technology, and AV systems.
• Coordinate with outside vendors (internet providers, AV companies, security companies, etc.) when necessary to resolve household technology issues.
• Set up, secure, and maintain family devices and ensure best practices for data protection and privacy.
• Provide day-to-day support for employees, including diagnosing and resolving hardware, software, and connectivity issues. Manage hardware updates ensuring timely compliance.
• Assist with onboarding/offboarding by coordinating with the MSP: setting up accounts, configuring laptops, installing applications, ensuring compliance with security protocols and training new employees.
• Maintain IT inventory and procure hardware/software for employees.
• Support and maintain office equipment including printers, AV systems, and conferencing tools including acting as main POC for vendors.
• Maintain domain names.
• Collaborate with external vendors to monitor performance and resolve issues identified during recurring cybersecurity audits and assessments.
• Monitor and maintain proper access controls across platforms (e.g., SharePoint).
• Technical troubleshooting: strong diagnostic skills for resolving hardware, software, and network issues across multiple platforms.
• Cybersecurity awareness: familiarity with cybersecurity best practices, including audit procedures, threat detection, and remediation. Experience in analyzing and interpreting vulnerability reports generated by MSP.
• Vendor management: experience coordinating with external IT service providers and managing service-level agreements.
• Discretion & confidentiality: proven ability to handle sensitive information with discretion, especially in a family office environment.
• System administration: knowledge of Windows, macOS, and mobile device management (MDM) systems.
• Documentation & reporting: skilled in maintaining IT documentation, asset inventories, and audit logs.

Required Skills/Abilities

• Bachelor’s degree in information technology, Computer Science, or a related field (or equivalent experience).
• 3–5 years of IT support experience, preferably in a private or family office setting.
• Certifications (preferred but not required):
• CompTIA A+ or Network+
• Microsoft Certified: Modern Desktop Administrator Associate
• Certified Information Systems Security Professional (CISSP) or equivalent

Job Details

• Seniority level: Mid-Senior level
• Employment type: Permanent/Part Time
• Job function: Information Technology
• Industries: Accounting

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