Executive IT Support Manager

Medasource; Chicago (IL); On-site; USD 95,000 - 130,000; Full time

Job summary

Medasource is seeking an Executive IT Support Manager / Senior Manager in Chicago, IL, to lead a small team and provide white-glove IT support to C‑suite executives. This role combines hands-on deskside troubleshooting with strategic leadership of HQ IT operations, ensuring reliable devices, collaboration tools, and secure access across Windows and macOS platforms.

The ideal candidate brings 8+ years of executive support experience, strong communication, and the ability to stay calm under

Qualifications

• 8+ years IT support, deskside, or executive support experience.
• Experience directly supporting CEO/C-suite executives.
• Leadership or supervision of a IT support team.

Responsibilities

• Provide white-glove tech support to CEO and senior executives.
• Lead day-to-day headquarters IT support operations.
• Troubleshoot Windows and macOS across devices and apps.
• Support executive meetings and AV/Rooms technology.

Skills

Executive support

Deskside support

Windows troubleshooting

macOS troubleshooting

Microsoft 365

Teams

Intune

Jamf

AV support

Executive presence

Education

Bachelor's degree in IT/CS/Business or related

Tools

ServiceNow

Jamf

Intune

Microsoft 365

Job description

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.