Executive IT Support Manager

Executive IT Support Manager / Senior Manager – Chicago, IL

We are hiring an experienced Executive IT Support Manager / Senior Manager for an urgent contract-to-hire opportunity supporting a large enterprise organization in downtown Chicago.

Location: Chicago, IL – Fulton Market

Work Setting: 100% Onsite

Schedule: Monday–Friday, approximately 8:00 AM–5:00 PM, with flexibility for occasional after-hours executive and event support

Contract: 4–6 months, with conversion to full-time

Travel: Approximately quarterly for executive and high-visibility meetings

Start: ASAP

This is a highly visible player-coach role combining IT leadership with direct, hands-on support for senior executives. The individual will oversee day-to-day headquarters IT support operations, lead Executive Support Engineers, and personally provide white-glove support to C-suite and other VIP users.

Key Responsibilities

• Provide hands-on, white-glove technology support to CEO, C-suite, and senior executive users
• Lead day-to-day headquarters IT support operations and provide direction to Executive Support Engineers
• Troubleshoot complex issues across Windows, macOS, Microsoft 365, Teams, Outlook, Intune, Jamf, mobile devices, connectivity, printers, peripherals, and workplace technology
• Support Microsoft Teams Rooms, conference rooms, AV technology, and high-visibility executive meetings
• Perform proactive technology health checks and ensure meeting spaces are tested and ready
• Support executive onboarding and other confidential technology needs
• Monitor support queues and ensure issues are appropriately owned and resolved
• Develop backup plans and quickly respond when technology issues arise during high-pressure meetings or events
• Provide occasional support for executives traveling or working from alternate locations

Required Experience

• 8+ years of progressive IT support, deskside, executive support, workplace technology, or related experience
• Significant hands-on experience directly supporting CEO, C-suite, SVP, or other senior executive users
• Previous IT leadership, team lead, or support management experience
• Strong hands-on troubleshooting across both Windows and macOS
• Strong Microsoft 365, Teams, Outlook, and Intune experience
• Experience with Jamf or similar MDM environments
• Experience supporting enterprise AV, Microsoft Teams Rooms, and high-profile meetings
• Ability to remain technically hands-on while leading day-to-day IT support operations
• Strong communication skills, discretion, organization, and executive presence
• Ability to remain calm and solutions-focused in high-pressure situations

Preferred

• Experience supporting Board, investor, executive leadership, or other high-visibility meetings
• ServiceNow experience
• ITIL, Microsoft, Apple, AVIXA/CTS, or related technical certifications
• Bachelor's degree in IT, Computer Science, Business, or a related area; equivalent experience may also be considered

The ideal candidate is a proactive, disciplined IT leader who can anticipate problems, prepare backup plans, lead a support team, and personally step in to resolve an executive technology issue when needed.