Executive Support IT Manager

We are seeking an experienced Executive IT Support Manager / Senior Manager to lead headquarters technology operations for their 20-30 person office location while providing white-glove support to the CEO and executive leadership team. This is a highly visible, hands-on leadership role responsible for ensuring seamless IT operations across the corporate headquarters while managing executive support, deskside services, conference room technology, standard technical support troubleshooting, and critical meeting readiness.

The ideal candidate is a player-coach who can effectively lead a small support team while remaining deeply technical and hands-on. This person will serve as the primary escalation point for executive technology issues, oversee high-profile Board of Directors and executive IT issues, and ensure a flawless technology experience for both onsite and remote employees.

Day-to-Day Responsibilities:

• Manage daily IT operations for the Chicago headquarters office and ensure all workplace technology services are functioning effectively.
• Lead and oversee a team of 2 Support Engineers responsible for deskside support and AV/conference room operations.
• Provide white-glove support to the CEO and executive leadership team.
• Serve as the primary escalation point for complex technical issues involving executive users.
• Monitor daily health checks, ticket queues, system readiness, and support team performance.
• Coordinate onboarding, offboarding, executive technology setup, confidential hires, and access management activities.
• Ensure executive travelers are properly configured for VPN access, geolocation groups, AI exception groups, and remote connectivity requirements.
• Support approximately 100 remote users and 20-30 headquarters employees.
• Partner with networking, infrastructure, security, and application teams to resolve issues impacting executive users.
• Lead preparation and technical validation for Board of Directors meetings, executive leadership meetings, investor events, and other high-visibility business events.
• Conduct proactive executive technology health checks, test calls, meeting readiness reviews, and post-event validation.
• Develop contingency plans and quickly restore service during critical technology outages or disruptions.
• Coordinate with third-party vendors and internal technology teams to ensure seamless service delivery.
• Participate in after-hours support, executive escalations, and critical business events as needed., Executive & White-Glove Support (40%)
• Personally support the CEO and executive leadership team with technology-related needs.
• Deliver a concierge-level support experience while maintaining professionalism, urgency, and discretion.
• Shield the broader support team from executive disruptions by owning escalated and high-priority issues.

Team Leadership (60%)

• Lead and mentor executive support and workplace technology personnel.
• Oversee team support operations, ticket management, service delivery metrics, and daily workload balancing.
• Drive operational excellence and ensure support processes are followed consistently.

Workplace Technology Operations

• Ensure conference rooms, collaboration tools, AV systems, and workplace technology are functioning properly.
• Own meeting readiness and event support for critical business functions.
• Partner with facilities and technology teams to support headquarters operations.

Technology & Systems Support

• Troubleshoot Windows and macOS endpoints.
• Support Microsoft 365 technologies including Teams, Outlook, OneDrive, and Office applications.
• Support Slack and collaboration platforms.
• Assist with Intune and JAMF device management environments.
• Troubleshoot issues across hardware, software, identity, networking, collaboration, and AV technologies.

• 8+ years of experience in Executive Support, Deskside Support, Workplace Technology, or End User Support within an enterprise environment.
• 3+ years of experience leading support teams, service desks, or workplace technology functions.
• Proven experience providing white-glove support to C-level executives, including CEO-level support.
• Strong experience supporting high-profile meetings, Board of Directors meetings, executive leadership meetings, and other business-critical events.
• Hands-on troubleshooting experience in both Windows and macOS environments.
• Experience managing and supporting Microsoft 365, including Teams, Outlook, and related collaboration tools.
• Experience with Intune and/or Jamf for endpoint management.
• Strong understanding of conference room technology, video conferencing, AV support, and meeting readiness.
• Ability to serve as the highest point of escalation for complex executive technology issues.
• Experience leading day-to-day IT support operations, managing ticket queues, escalations, service levels, and operational health checks.
• Exceptional communication skills, executive presence, and ability to interact confidently with senior leadership.
• Willingness to provide after-hours support and be on-call for executive needs, board meetings, and critical business events. - Bachelor’s degree in Information Technology, Computer Science, Business, or a related field.
• ITIL Certification.
• Microsoft Certifications.
• Apple Certifications.
• AVIXA CTS Certification.