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Remote Connectwise Jobs in Silver Spring, MD (NOW HIRING)

Experience using a helpdesk ticketing system for incident tracking and time entry (ConnectWise Manage preferred) * Prior experience using Remote Monitoring and Management (RMM) tools (i.e. - Automate ...

Helpdesk Technician I

Reston, VA · Remote

$20.75 - $28/hr

Experience using a helpdesk ticketing system for incident tracking and time entry (ConnectWise Manage preferred)  * Prior experience using Remote Monitoring and Management (RMM) tools (i.e ...

Experience with any remote-control tools including TeamViewer, Splashtop, AnyDesk, ConnectWise. * Experience with TCP/IP protocols, especially SNMP, TCP, UDP, ICMP, DN; will make you a good fit for ...

Experience with any remote-control tools including TeamViewer, Splashtop, AnyDesk, ConnectWise. * Experience with TCP/IP protocols, especially SNMP, TCP, UDP, ICMP, DN; will make you a good fit for ...

Remote Connectwise information

See Silver Spring, MD salary details

$15

$28

$39

How much do remote connectwise jobs pay per hour?

As of May 29, 2026, the average hourly pay for remote connectwise in Silver Spring, MD is $28.61, according to ZipRecruiter salary data. Most workers in this role earn between $22.36 and $34.28 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 Silver Spring, MD? The most popular types of Connectwise jobs in Silver Spring, MD are:
What are popular job titles related to Remote Connectwise jobs in Silver Spring, MD? For Remote Connectwise jobs in Silver Spring, MD, the most frequently searched job titles are:
What job categories do people searching Remote Connectwise jobs in Silver Spring, MD look for? The top searched job categories for Remote Connectwise jobs in Silver Spring, MD are:

Helpdesk Technician II

CyberSheath

Reston, VA • Remote

$83/hr

Full-time

Posted 9 days ago


Job description

CyberSheath Services International LLC is a rapidly growing Security and IT Managed Services Provider primarily focused on providing Cybersecurity services to the Defense Industrial Base (DIB). We are excited to be expanding our staff due to our growth and are looking to add an additional Helpdesk Technician Level II to our team!

CyberSheath integrates compliance and threat mitigation efforts and eliminates redundant security practices that don't improve and, in fact, may weaken an organization's security posture. Our professionals tell clients where to stop spending, where to invest, and how to take what they are already doing and integrate it in a way that delivers improved security.

Successful candidates for CyberSheath are self-motivated, think out of the box, work, and solve issues independently. Additionally, our most successful people are self-starters and willing to put on many hats in order to succeed. CyberSheath is fast-growing and seeks candidates who want to be part of our upward trajectory.

The Helpdesk Technician Level II provides day to day support for the implementation, troubleshooting, and maintenance of client IT systems, managing client IT system infrastructure and any process related to these systems. The ideal candidate will possess a detailed understanding of diverse IT systems, both On-premise and Cloud environments, and apply that understanding to provide support to CyberSheath customer's systems, networks, and applications. Consistently providing both excellent customer service and astute technical support is imperative to success in this role.

Essential Responsibilities (included but not limited to):

  • Ability to provide exceptional customer support in a fast-paced remote Managed Services Practice

  • Remotely troubleshoot and resolve client requests involving end-user hardware, software, and cloud services

  • Provide day-to-day operational support for:

  • Desktop and Server Operating Systems (Windows, Mac, Linux)

  • Microsoft Office 365, Azure, Teams, OneDrive, SharePoint

  • Networking Devices (firewalls, switches, wireless access points)

  • Line of Business Applications

  • On-premise and Cloud Backup and Disaster Recovery

  • Hardware peripherals (printers, monitors, docking stations, webcams, etc.)

  • Mobile Devices / Mobile Device Management (MAM / MDM)

  • Provide escalation support as necessary for Level I Helpdesk staff

  • Assist with the onboarding and offboarding of clients, systems, and users

  • Deploy and maintain security tools and management agents

  • Maintain current notes and time entries for all requests in the helpdesk ticketing system

  • Create and maintain comprehensive documentation for internal and client systems

  • Work with third-party vendors to remediate issues as needed

Required Education, Experience, & Skills

  • Minimum 2+ years working for a Managed Service Provider (MSP)

  • Minimum of 5+ years' experience working on an Information Technology Helpdesk using remote support tools

  • Experience using a helpdesk ticketing system for incident tracking and time entry (ConnectWise Manage preferred)

  • Prior experience using Remote Monitoring and Management (RMM) tools (i.e. – Automate, Labtech, Continuum, NinjaOne, etc.)

  • Ability to provide exceptional customer service in all situations

  • Possess strong troubleshooting, problem-solving, and verbal/written communication skills

  • Experience with Microsoft Windows desktop and server operating systems

  • Experience with Microsoft Office 365 / Azure administration

  • Proficiency with Microsoft Server Active Directory / Group Policy

  • Moderate networking experience including remote configuration and troubleshooting (TCP/IP, WIFI, VPN)

  • Knowledge of Microsoft Cloud Technologies including Office 365, Azure, Azure Entra ID, Endpoint Protection, Intune, Autopilot, etc.

  • Knowledge of scripting and automation tools a plus

  • Demonstrated ability to work in a team environment

  • Must be authorized to work for any employer in the U.S

Preferred Education, Experience, & Skills

  • Bachelor's degree from an accredited university in Computer Science, Engineering, or a related field

  • Experience with Security Technologies:

  • Multifactor Authentication

  • Encryption

  • SIEM/SOAR

  • Endpoint Detection and Response

  • Preferred Certifications:

  • Microsoft MD100/101, AZ900, AZ104, CompTIA Security+, Network+

  • Excellent organizational skills including the ability to balance conflicting priorities

  • Ability to work independently, remotely, and as part of a team

Work Environment

  • This role is Remote with the potential for travel to client sites

  • Travel expectations - approximately 20%
  • Some on-call, shift, and evening work

CyberSheath is an Equal Opportunity Employer. All qualified applicants will receive consideration for employment without regard to race, color, religion, sex, gender identity, national origin, age, protected veteran status, among other things, or status as a qualified individual with a disability.

#LI_Remote

Budgeted Pay Range
$70,000—$83,000 USD