W2 Role :: Executive It Support Manager / Senior Manager :: Chicago, IL

Job Title Executive It Support Manager / Senior Manager

Location Chicago, IL

Duration 12 Month

W2 only

Top technical requirements include:

• Hands-on experience providing white-glove IT support to executive/VIP users
• Strong working knowledge of Microsoft 365, Teams, Intune, Windows, and macOS
• Experience troubleshooting AV/conferencing technology and supporting high-visibility meetings

Top soft skill requirements include:

• Strong executive presence and communication skills
• Ability to remain calm, professional, and solutions-focused under pressure
• A resourceful and proactive mindset, with the ability to think on their feet, anticipate needs, and have a Plan B
  
  
  
  

Overseeing all IT Support at Headquarters and Sr Executive Support onsite and remote.

• Ability to manage teams and day to day ops of an office
• 5 days on site
• Hands on and close with technology
• Understands the value of time for C level executives, and being on time!
• Will need to work with Board of Directors, Partners for quarterly meetings and high visibility meetings that this person will travel to wherever these meetings are. These are planning opportunities to ensure all details are planned for from a technology standpoint.
• AV Engineer will be handling conference rooms, so will need some experience with AV
• Device Imaging is a big part of the support they will do, so need to understand that.
• 100 remote users they will be supporting from an SVP, VP level, but

• What does "white-glove support" mean to your executive team on a day-to-day basis? It would start with ensuring and always being available during business hours, support when needed. Essentially available on stand by to execute these requests. Make sure that meetings happening at HQ are run seamless from a tech standpoint. Someone that can constantly run a health check for these tech related.

• How do you balance the leadership aspect of the role versus the hands-on executive support responsibilities? In a typical week, what percentage of time would you expect this person to spend managing the team, planning for executive events, and personally supporting the CEO and leadership team? 60/40 split 60% managing the team and working through the tickets that are in their queue, printers working, health checks, plan for meetings and 40% doing support themselves more directly to the CEO himself, his executive assistant and his 1 down executive that reports into him that sits in Chicago. Handling a high level temperament.

• TECHNOLOGY STACK
• Windows/MAC environment
• Windows Troubleshooting
• MAC OS Troubleshooting
• Intune imaging tool
• Microsoft Shop
• Teams
• Outlook
• M365 Suite
• AV Technology familiarity
• Geo-Location experience to give exceptions to use their internal systems in specific locations.
• AI Exception Groups and provision who has access to what AI Provisions
• Onboarding/Offboarding activities

Position Summary

The Executive IT Support Manager / Senior Manager is a highly visible, hands-on technology leader responsible for the end-to-end delivery of headquarters IT support, including executive technology support, deskside services, conference room and audiovisual operations, and critical meeting readiness. The role personally provides white-glove support to the CEO and the CEO's direct reports while leading two Executive Support Engineers and coordinating across internal technology teams and external vendors.

Success requires a rare combination of deep technical capability, executive presence, discretion, calm decision-making, and meticulous preparation. The incumbent anticipates risks, develops practical Plan B and Plan C contingencies, and restores service quickly and professionally when technology fails. The role owns the flawless technical execution of Board of Directors, investor, executive leadership, and other high-stakes meetings where service quality, confidentiality, and business continuity are critical.

Leadership profile: A player-coach who can lead the headquarters support function, personally resolve complex issues, and create confidence for senior executives during time-sensitive, high-pressure situations.

Essential Responsibilities

Executive and VIP Technology Support

Provide direct, hands-on, white-glove technology support to the CEO, the CEO's direct reports, Board members, and other designated executives, including support in offices, meeting spaces, during travel, and remotely as business needs require.

Build trusted relationships with executives and executive assistants by demonstrating discretion, empathy, situational awareness, concise communication, and disciplined follow-through.

Own complex and escalated incidents from intake through resolution, keeping stakeholders informed without creating unnecessary technical noise or disruption.

Anticipate executive needs by reviewing schedules and upcoming events, validating technology in advance, and preparing backup devices, connectivity, presentation methods, and support coverage.

Handle confidential and sensitive information with the highest level of integrity and sound judgment.

Board, Investor and High-Stakes Meeting Support

Lead the technical planning and execution of Board of Directors, investor, earnings, executive leadership, town hall, and other mission-critical meetings.

Create and execute readiness plans, including room validation, device testing, AV and collaboration checks, content and presentation testing, connectivity verification, dry runs, support staffing, and stakeholder communications.

Develop and maintain documented Plan B and Plan C contingencies for common failure scenarios, including device, display, audio, conferencing, network, power, access, and presentation failures.

Provide discreet real-time support during live meetings, rapidly isolate issues, make risk-based decisions, and recover service with minimal impact to the audience.

Coordinate with executive assistants, Corporate Communications, Facilities, Security, Network, Collaboration, vendors, and other partners to ensure clear ownership and seamless delivery.

Conduct post-event reviews for material issues and implement corrective actions to prevent recurrence.

Headquarters IT Support and AV Operations

Own the overall headquarters IT support experience, including deskside support, conference rooms, Microsoft Teams Rooms, audiovisual technology, executive offices, printers, peripherals, and related workplace technology.

Executive IT Support Manager / Senior Manager | Confidential Job Profile

Serve as the senior escalation point for headquarters incidents and service requests, personally troubleshooting when needed and mobilizing the correct resolver teams for issues outside the team's direct control.

Ensure conference rooms and AV systems remain secure, current, and operational through preventive maintenance, firmware and software updates, testing, lifecycle planning, and vendor coordination.

Manage device setup, imaging, configuration, operating system and application troubleshooting, connectivity, peripherals, and executive mobility needs across Windows and macOS environments.

Maintain accurate procedures, support playbooks, event checklists, knowledge articles, inventory records, and escalation contacts.

Partner with Facilities and workplace teams on headquarters technology changes, office moves, buildouts, conference room upgrades, and business continuity requirements.

Team Leadership and Service Management

Lead, coach, and develop two Executive Support Engineers; establish schedules, on-call and event coverage, clear

responsibilities, performance expectations, and technical development plans.

Balance day-to-day operational demand with proactive maintenance, project delivery, executive needs, and high-priority events.

Establish service standards and measurable operating routines for responsiveness, communication, incident ownership, meeting readiness, documentation, and customer experience.

Monitor incidents, requests, trends, recurring failures, and service risks; drive root-cause analysis and continuous

improvement.

Manage vendor relationships and support engagements for AV, conferencing, hardware, and specialized executive support services.

Contribute to technology roadmaps, standards, lifecycle plans, budget inputs, and projects affecting headquarters and executive users.

Required Technical Expertise

Advanced troubleshooting and support experience with Windows 11, macOS, laptops, desktops, mobile devices, printers, monitors, docks, peripherals, device imaging, drivers, and hardware diagnostics.

Strong knowledge of Microsoft 365 applications and services used in day-to-day support, including Outlook, Teams, OneDrive, SharePoint, Office applications, Intune, Entra ID / Active Directory concepts, and remote support tools.

Demonstrated expertise with enterprise AV and collaboration technology, including Microsoft Teams Rooms, cameras, microphones, speakers, displays, room control systems, wired and wireless presentation, and live meeting troubleshooting.

Working knowledge of networking and connectivity concepts, including Wi-Fi, wired networks, VPN, DNS, DHCP,

authentication, conferencing traffic, and systematic isolation of endpoint versus infrastructure issues.

Experience with IT service management tools and disciplines, including incident, request, problem, change, knowledge, asset, and vendor management.

Ability to read technical documentation, interpret logs and error information, engage specialized engineering teams, and translate technical issues into concise business language.

Leadership and Behavioral Competencies

Executive presence and emotional composure: remains calm, respectful, and decisive when expectations are high, time is limited, or multiple stakeholders are under pressure.

Exceptional interpersonal judgment: adapts communication and support approach to the preferences, working styles, and urgency of senior executives without compromising policy, security, or professionalism.

Proactive risk management: thinks several steps ahead, identifies points of failure, validates assumptions, and prepares credible alternatives before critical moments.

Ownership and accountability: stays engaged until service is restored, communicates clearly, closes loops, and ensures corrective actions are completed.

Discretion and confidentiality: protects sensitive executive, Board, investor, personnel, and company information.

Operational discipline: builds repeatable processes, clear roles, checklists, escalation paths, service expectations, and documentation while remaining agile during incidents.

Strong written and verbal communication, including the ability to brief executives, coordinate technical teams, and de-escalate difficult interactions with poise.

Ability to prioritize multiple simultaneous demands and make sound, risk-based decisions with limited supervision.

Executive IT Support Manager / Senior Manager | Confidential Job Profile

Education and Experience

Bachelor's degree in Information Technology, Computer Science, Business, or a related field preferred. Equivalent relevant experience may be considered.

8+ years of progressive end-user, deskside, executive, workplace technology, or AV support experience, including significant direct support of C-suite or senior executive customers.

3+ years of people leadership, team lead, or service ownership experience in a high-touch enterprise IT environment.

Demonstrated experience leading the technology delivery for Board, investor, executive leadership, or similarly high

consequence meetings and events.

Experience supporting both Windows and macOS in an enterprise environment and managing issues that cross endpoint, identity, collaboration, network, and AV domains.

ITIL, Microsoft, Apple, AVIXA / CTS, or relevant technical certifications are preferred but not required.

Work Requirements

Primarily on-site at headquarters due to the hands-on and event-driven nature of the role.

Flexibility to provide early morning, evening, weekend, after-hours, and on-call support for executives, critical incidents, and scheduled Board or investor events.

Occasional travel and support at alternate business or executive locations may be required.

Ability to move and install common workplace technology equipment and safely perform hands-on troubleshooting in offices, conference rooms, and technology spaces.

Reasonable accommodations may be made to enable individuals to perform the essential responsibilities of the position.

Success Measures

Executive and headquarters stakeholders experience responsive, discreet, and dependable technology support.

Board, investor, and executive meetings are fully tested, supported, and delivered with effective contingency coverage.

Critical incidents are contained quickly, communications are clear, and repeat failures are reduced through corrective action.

Conference rooms, AV systems, and executive devices are maintained proactively and remain ready for business use.

Team coverage, ownership, documentation, and escalation paths are clear and consistently followed.

Thanks & Regards

Akshit Sisonia - Sr. Technical Recruiter

Email - View email address on us.fitly.work

LinkedIn - linkedin.com/in/akshit-s-97297125a

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