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Remote Connectwise Jobs in Chicago, IL (NOW HIRING)

GeorgeJon

Delivery Manager - US

Chicago, IL · Remote

This is a remote position. RESPONSIBILITIES * Own delivery for assigned engagements, accountable ... Comfortable in service and project management tools (e.g., ConnectWise, Asana) with disciplined ...

George Jon, Inc.

Delivery Manager - US

Chicago, IL · On-site +1

This is a remote position. RESPONSIBILITIES * Own delivery for assigned engagements, accountable ... Comfortable in service and project management tools (e.g., ConnectWise, Asana) with disciplined ...

Baxter and Woodman Inc

IT Consultant

Chicago, IL · On-site +1

$90K - $120K/yr

Provide on-site and remote technical support as needed and participate in a rotating on-call ... Experience with ConnectWise or similar IT service management / PSA platforms. * Relevant industry ...

Baxter and Woodman Inc

IT Consultant

Naperville, IL · On-site +1

$90K - $120K/yr

Provide on-site and remote technical support as needed and participate in a rotating on-call ... Experience with ConnectWise or similar IT service management / PSA platforms. * Relevant industry ...

Baxter and Woodman Inc

IT Consultant

Crystal Lake, IL · On-site +1

$90K - $120K/yr

Provide on-site and remote technical support as needed and participate in a rotating on-call ... Experience with ConnectWise or similar IT service management / PSA platforms. * Relevant industry ...

Baxter & Woodman

IT Consultant

Bannockburn, IL · On-site +1

$90K - $120K/yr

Provide on-site and remote technical support as needed and participate in a rotating on-call ... Experience with ConnectWise or similar IT service management / PSA platforms. * Relevant industry ...

Baxter and Woodman Inc

IT Consultant

Deerfield, IL · On-site +1

$90K - $120K/yr

Provide on-site and remote technical support as needed and participate in a rotating on-call ... Experience with ConnectWise or similar IT service management / PSA platforms. * Relevant industry ...

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Remote Connectwise information

See Chicago, IL salary details

$15

$28

$38

How much do remote connectwise jobs pay per hour?

As of May 28, 2026, the average hourly pay for remote connectwise in Chicago, IL is $28.51, according to ZipRecruiter salary data. Most workers in this role earn between $22.31 and $34.18 per hour, depending on experience, location, and employer.

What are the key skills and qualifications needed to thrive as a Remote ConnectWise Specialist, and why are they important?

To thrive as a Remote ConnectWise Specialist, you need a solid understanding of IT service management, experience with ConnectWise software, and often a background in computer science or related fields. Familiarity with ConnectWise Manage, Automate, and Control platforms, as well as relevant certifications like ConnectWise certifications or CompTIA A+, is typically required. Strong problem-solving, communication, and customer service skills help specialists efficiently resolve client issues and work collaboratively with remote teams. These abilities are crucial for delivering high-quality IT support, maintaining system integrity, and ensuring client satisfaction in a remote environment.

How does a Remote ConnectWise professional typically collaborate with IT teams and clients?

As a Remote ConnectWise professional, you'll regularly interact with internal IT teams and external clients to manage service tickets, coordinate project tasks, and resolve technical issues. Collaboration often involves using ConnectWise's integrated communication tools, remote access features, and documentation systems to ensure everyone stays updated and aligned. You'll participate in virtual meetings, provide remote support, and frequently share progress reports or troubleshooting steps. Strong communication skills and proactive follow-ups are key to building trust and ensuring smooth workflows in a remote setting.

What is a Remote ConnectWise technician?

A Remote ConnectWise technician is an IT professional who uses ConnectWise, a popular remote monitoring and management (RMM) software, to provide technical support and manage client systems from a remote location. They help businesses monitor their IT infrastructure, troubleshoot issues, and perform maintenance tasks without needing to be physically present. This role is essential for managed service providers (MSPs) and companies that rely on remote IT support to ensure their networks and devices run smoothly.

What is the difference between Remote Connectwise vs Remote Autotask Technician?

AspectRemote ConnectwiseRemote Autotask Technician
CertificationsConnectWise certifications, ITILAutotask certifications, CompTIA A+
Work EnvironmentRemote support for MSPs, IT service providersRemote troubleshooting for MSPs, IT firms
Industry UsageWidely used in managed service providersCommon in IT service management companies

Remote Connectwise and Remote Autotask Technicians both support IT service providers remotely, often requiring similar certifications and working in comparable environments. The main difference lies in the specific platform expertise: Connectwise focuses on ConnectWise Manage, while Autotask technicians specialize in Autotask PSA. Both roles are essential in MSP operations, with overlapping skills but platform-specific knowledge.

What are the most commonly searched types of Connectwise jobs in Chicago, IL? The most popular types of Connectwise jobs in Chicago, IL are:
What are popular job titles related to Remote Connectwise jobs in Chicago, IL? For Remote Connectwise jobs in Chicago, IL, the most frequently searched job titles are:
What job categories do people searching Remote Connectwise jobs in Chicago, IL look for? The top searched job categories for Remote Connectwise jobs in Chicago, IL are:
Remote Connectwise jobs near you
VIP Technical Support Specialist - Hospitality Industry (Chicago Metro Area)

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

Nexplay Consulting Inc.

Chicago, IL • On-site, Remote

$25 - $30/hr

Full-time

Posted 11 days ago

Job description

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.

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