VIP Technical Support Specialist - Hospitality Industry (Chicago Metro Area)

About the Role
We are seeking a highly professional, customer-obsessed VIP Technical Support Specialist based in the Chicago Metro Area to deliver exceptional, white-glove IT support to hotel executives, management teams, and VIP stakeholders in the hospitality industry. This is a full-time remote position with a guaranteed 40 hours per week, where you'll serve as a trusted technical concierge—ensuring seamless technology experiences for high-profile users who demand precision, discretion, and rapid resolution. You'll work closely with our helpdesk team, handle incoming support calls, troubleshoot complex issues across devices and networks, and occasionally travel for onsite visits as needs evolve. If you thrive in fast-paced, high-touch environments, have a passion for hospitality combined with strong IT skills,  and are located in the LA metro area , this is your opportunity to make a real impact

Key Responsibilities

• Provide  white-glove, VIP-level technical support to hotel executives, general managers, and senior leadership via phone, email, remote sessions, and ticketing system.
• Answer and manage  incoming support calls promptly and professionally, delivering personalized, concierge-style service.
• Deliver  exceptional customer service in every interaction, prioritizing empathy, responsiveness, and a genuine hospitality mindset to exceed expectations of high-profile clients.
• Collaborate closely with the helpdesk team to resolve issues efficiently and escalate when needed.
• Diagnose and troubleshoot a wide range of technical problems, including  Windows and macOS systems ,  iPhone and Android devices , software applications, and  networking issues (Wi-Fi, connectivity, VPN, etc.).
• Exhibit  superb troubleshooting skills , quick thinking, and the ability to identify root causes under pressure.
• Maintain detailed records in  Autotask (or similar ticketing system) while following and providing clear instructions to users and team members.
• Ensure all interactions reflect  polished, presentable communication (verbal and written) with a focus on empathy, clarity, and professionalism.
• Participate as a  team player , supporting colleagues and contributing to continuous improvement.
• Be prepared for occasional  onsite visits to hotels or client locations for hands-on support or assessments (travel expenses covered per company policy, to be discussed in detail).

Qualifications & Requirements

• Candidates must reside in the Chicago metropolitan region and be available to commute to client sites. The position is hybrid, beginning with remote work but potentially shifting to include more on-site presence depending on client demands. Travel for hands-on support at client or hotel locations will be required (reimbursed per company travel policy; further details to be reviewed).
• Proven  hospitality industry experience (e.g., hotel operations, executive support, concierge services, or similar high-touch guest/client environments).
• Strong  IT technical background with hands-on experience supporting  Windows ,  macOS ,  iOS (iPhone) , and  Android devices.
• Demonstrated expertise in  troubleshooting networking issues (e.g., connectivity, routers, firewalls, basic configurations).
• Familiarity with  Autotask or equivalent PSA/ticketing systems (e.g., ConnectWise, ServiceNow, Zendesk).
• Exceptional  communication skills —articulate, professional, and able to explain technical concepts to non-technical executives clearly and patiently.
• Quick-witted problem-solver with the ability to think on your feet and resolve issues efficiently.
• Highly  presentable demeanor suitable for interacting with senior executives and VIPs.
• Team-oriented mindset: follows instructions precisely, provides clear guidance to others, and collaborates effectively.
• Reliable, self-motivated remote worker with a professional home setup (quiet workspace, strong internet, headset, etc.).

Preferred Qualifications (Nice-to-Haves)

• Previous experience in  VIP/executive IT support or concierge-level tech assistance.
• Certifications such as CompTIA A+, Network+, Microsoft Certified: Modern Desktop Administrator, or similar.
• Familiarity with hospitality-specific software (e.g., PMS systems like Opera, guest Wi-Fi platforms, AV/conference tools).
• Willingness and availability for occasional travel (domestic, short-notice onsite support).

What We Offer

• Full-time remote position with  guaranteed 40 hours/week .
• Competitive compensation + benefits (details discussed in interview).
• Opportunity to work with luxury hospitality clients and grow in a dynamic, high-service environment.
• Supportive team culture focused on excellence and work-life balance.

If you're a polished professional who combines genuine hospitality instincts with top-tier technical troubleshooting—and you excel at delivering calm, confident support under pressure—we'd love to hear from you!  Only applicants in the Chicago area will be considered at this time. Apply today to join our team and elevate VIP experiences in hospitality.