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

Ntiva

Contract Analyst

Mclean, VA · On-site +1

$65K - $75K/yr

This is a remote position; however, team members should be willing and able to travel if the need ... Create and maintain recurring client agreements within ConnectWise and related systems. * Configure ...

Ntiva

Contract Analyst

Mclean, VA · Remote

$65K - $75K/yr

This is a remote position; however, team members should be willing and able to travel if the need ... Create and maintain recurring client agreements within ConnectWise and related systems. * Configure ...

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All JobsConnectwise JobsRemote Connectwise JobsRemote Connectwise Jobs in Silver Spring, MD

Remote Connectwise information

See Silver Spring, MD salary details

$15

$28

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How much do remote connectwise jobs pay per hour?

As of Sep 7, 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 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.

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 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.

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:

What cities near Silver Spring, MD are hiring for Remote Connectwise jobs?

Cities near Silver Spring, MD with the most Remote Connectwise job openings:

Remote Connectwise jobs near you

Jr. Systems Administrator

Paragone Solutions, Inc.

Mclean, VA • On-site, Remote

Part-time

Re-posted 13 days ago

Key responsibilities

  • Install, configure, maintain, and troubleshoot Windows workstations, servers, and Microsoft 365 environments.

  • Administer user accounts in Microsoft Entra ID (Azure AD) and Active Directory.

  • Assist with system deployments, user administration, endpoint management, patch management, vulnerability remediation, and security operations.

Job description

The Junior Systems Administrator is responsible for the day-to-day administration, maintenance, and support of Windows-based information systems, cloud services, and end-user computing environments. Working under the guidance of senior technical staff, the Junior Systems Administrator assists with system deployments, user administration, endpoint management, patch management, vulnerability remediation, and security operations while ensuring systems remain reliable, secure, and compliant with organizational policies.
Note, this position will begin as a part time role.
This position provides an excellent opportunity for an early-career IT professional to develop expertise in Microsoft technologies, cybersecurity, cloud administration, and enterprise IT operations.
Primary Responsibilities
  • Install, configure, maintain, and troubleshoot Windows workstations, servers, and Microsoft 365 environments
  • Administer user accounts in Microsoft Entra ID (Azure AD) and Active Directory
  • Deploy and manage Windows devices using Microsoft Intune
  • Provide technical support for hardware, software, printers, mobile devices, and end users
  • Perform operating system updates, patch management, and vulnerability remediation
  • Monitor system performance, endpoint compliance, backups, and security alerts
  • Assist with server upgrades, migrations, and technology deployments
  • Maintain accurate system documentation, asset inventories, and change records
  • Support cybersecurity initiatives and compliance with frameworks such as CMMC and NIST SP 800-171
  • Collaborate with senior administrators to troubleshoot issues and improve IT operations
  • Travel occasionally to customer sites or company locations (approximately one to two trips per year, averaging three days per trip)

Required Qualifications
  • Experience in IT systems administration, technical support, or help desk
  • Working knowledge of Windows operating systems and Microsoft 365
  • Familiarity with Active Directory and/or Microsoft Entra ID
  • Basic networking knowledge (TCP/IP, DNS, DHCP)
  • Strong troubleshooting, analytical, and communication skills
  • Excellent organizational skills and attention to detail
  • Due to the requirements of this position, applicants must be U.S. citizens and authorized to work in the United States.

Technical Requirements
Candidates should demonstrate the ability to perform the following tasks with minimal supervision:
  • Configure and deploy Windows 11 workstations in accordance with organizational standards
  • Perform a complete Windows 11 operating system reset, reinstallation, and recovery while preserving or restoring required system functionality
  • Build a Windows 11 computer from bare hardware through delivery to the end user, including:
    • Installing Windows 11
    • Applying operating system updates
    • Installing hardware drivers
    • Configuring BIOS/UEFI settings as required
    • Joining devices to Microsoft Entra ID or Active Directory
    • Enrolling devices in Microsoft Intune
    • Applying security baselines and configuration policies
    • Installing and configuring required business applications
    • Configuring Microsoft 365 applications and user profiles
    • Enabling Microsoft Defender security features
    • Verifying device compliance and operational readiness
  • Troubleshoot Windows startup, operating system, hardware driver, and application issues
  • Install, configure, and update desktop software and security applications
  • Understand Windows file systems, user profiles, local security settings, and system configuration tools
  • Utilize PowerShell and administrative utilities to perform common system administration tasks.
  • Follow documented build procedures and configuration standards to ensure consistent, repeatable workstation deployments

Preferred Qualifications and Certifications
  • Experience with Microsoft Intune, Microsoft Defender, Windows Server, Hyper-V or VMware, and PowerShell
  • Familiarity with vulnerability management and remote monitoring tools
  • Experience supporting cloud environments
  • Exposure to cybersecurity concepts and best practices
  • Experience with ticketing systems such as Autotask, ConnectWise, or ServiceNow
  • Prior military experience is highly desired
  • CompTIA A+, Network+, or Security+
  • Microsoft Azure Fundamentals (AZ-900)
  • Microsoft 365 Fundamentals (MS-900)
  • Microsoft Certified: Endpoint Administrator Associate

SecureITSM, a division of Paragone Solutions, Inc,. is an IT Managed Service Provider (MSP) supporting DoD contractors who must comply with Cybersecurity Maturity Model Certification (CMMC) requirements. SecureITSM also supports commercial entities that must maintain a high level of cybersecurity hygiene. SecureITSM offers competitive salaries, benefits and a relaxed, life-friendly work environment.
All qualified applicants will receive consideration for employment without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, disability, or status as a protected veteran.

Apply