Executive IT Support Manager / Senior Manager

Location: Chicago, IL Salary: $50.00 USD Hourly - $55.00 USD Hourly Description:
Executive IT Support Manager / Senior Manager

Location: Chicago, IL (Onsite - 5 Days/Week)
Job Type: Contract-to-Hire
About the Opportunity

We are seeking an experienced Executive IT Support Manager / Senior Manager to lead headquarters IT support operations while providing hands-on, white-glove technology support to executive leadership. This is a highly visible role supporting C-suite executives, Board members, and senior leadership while overseeing a small team responsible for executive support services, AV technologies, and workplace technology operations.

The ideal candidate is a hands-on "player-coach" with exceptional executive presence, strong technical expertise, and the ability to thrive in high-pressure environments where reliability, responsiveness, and discretion are critical.
Key Responsibilities
Executive & VIP Support

• Provide white-glove IT support to senior executives, including the CEO and executive leadership team.
• Serve as the primary escalation point for complex technical issues impacting executive users.
• Anticipate executive needs by proactively validating devices, connectivity, meeting technology, and support readiness.
• Support executives both onsite and remotely, ensuring a seamless technology experience.
• Build trusted relationships with executives and executive assistants through professionalism, responsiveness, and discretion.

Leadership & Team Management

• Lead and mentor a team of Executive Support Engineers.
• Manage day-to-day headquarters support operations, ticket queues, escalations, and service delivery.
• Establish service standards and ensure consistent execution of support processes.
• Balance operational leadership responsibilities with direct hands-on support.
• Drive continuous improvement initiatives and root-cause analysis efforts.

Board Meetings & High-Visibility Events

• Plan and execute technology support for Board meetings, executive leadership sessions, investor events, and other high-profile meetings.
• Coordinate with executive assistants, facilities, security, communications teams, vendors, and technology partners.
• Conduct room readiness reviews, AV testing, connectivity validation, and meeting rehearsals.
• Develop contingency plans and backup solutions to ensure flawless event execution.
• Provide live support during critical meetings and rapidly resolve technical issues when they arise.

Headquarters IT Operations

• Oversee headquarters technology support including:
  • Deskside support
  • Conference rooms
  • Microsoft Teams Rooms
  • Printers and peripherals
  • Executive offices
  • Audiovisual (AV) systems
• Manage device setup, imaging, deployment, troubleshooting, and lifecycle activities.
• Maintain documentation, support playbooks, inventory records, and knowledge articles.
• Partner with facilities and workplace services on office moves, upgrades, and technology projects.

Required Qualifications
Technical Skills

• 8+ years of IT support experience in enterprise environments.
• Significant experience providing executive and VIP technology support.
• Expertise supporting both Windows and macOS environments.
• Experience with:
  • Microsoft 365
  • Microsoft Teams
  • Outlook
  • OneDrive
  • SharePoint
  • Intune
  • Entra ID / Active Directory
• Strong device imaging and deployment experience.
• Hands-on troubleshooting experience with:
  • Laptops and desktops
  • Mobile devices
  • Printers and peripherals
  • Docking stations and monitors
• Experience supporting AV and conferencing technologies, including:
  • Microsoft Teams Rooms
  • Cameras
  • Microphones
  • Presentation systems
  • Conference room technology
• Working knowledge of networking concepts including:
  • Wi-Fi
  • VPN
  • DNS
  • DHCP
  • Authentication technologies

Leadership Experience

• 3+ years of team leadership, management, or service ownership experience.
• Experience leading support operations in a high-touch enterprise environment.
• Proven ability to manage multiple priorities while maintaining exceptional customer service.

Preferred Qualifications

• Bachelor's degree in Information Technology, Computer Science, Business, or a related field.
• ITIL, Microsoft, Apple, CTS/AVIXA, or other relevant certifications.
• Experience supporting Board of Directors meetings, executive leadership events, or similarly high-stakes environments.

Desired Soft Skills

• Strong executive presence and communication skills.
• Ability to remain calm and professional under pressure.
• Excellent problem-solving and troubleshooting capabilities.
• Proactive mindset with the ability to anticipate issues before they occur.
• Strong attention to detail and organizational skills.
• Exceptional discretion when handling confidential information.
• Ability to create contingency plans and quickly adapt when circumstances change.

Work Environment

• 100% onsite at the Chicago headquarters.
• Flexibility to support early morning, evening, weekend, and after-hours executive events when required.
• Occasional travel may be necessary to support leadership meetings and corporate events.
• Hands-on role requiring physical interaction with workplace technology equipment and conference room technology.

Medical, dental, and vision insurance are available to qualified candidates who meet eligibility requirements.
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