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Remote Connectwise Jobs in Wisconsin (NOW HIRING)

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Remote Connectwise information

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 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 are the most commonly searched types of Connectwise jobs in Wisconsin?

The most popular types of Connectwise jobs in Wisconsin are:

What are popular job titles related to Remote Connectwise jobs in Wisconsin?

For Remote Connectwise jobs in Wisconsin, the most frequently searched job titles are:

What job categories do people searching Remote Connectwise jobs in Wisconsin look for?

The top searched job categories for Remote Connectwise jobs in Wisconsin are:

What cities in Wisconsin are hiring for Remote Connectwise jobs?

Cities in Wisconsin with the most Remote Connectwise job openings:

Remote Connectwise jobs near you
Infographic showing various Remote Connectwise job openings in Wisconsin as of August 2026, with employment types broken down into 67% Full Time, and 33% Part Time. Highlights an 100% Remote job distribution.

Service Lead (Remote)

PeopleWise Consulting MN

Superior, WI • Remote

Full-time

Re-posted 13 days ago

Job description

DSC Communications is seeking a Service Team Lead to anchor our managed services support structure. This is a hands-on technical leadership role which requires active participation in client issues and requests. The right person owns L2/L3 escalations, drives quality across the service queue, holds outsourced partners accountable, and helps build the processes and documentation that make the team more effective over time.

DSC Sentinel iQ is being purpose-built as an automation-first, AI-driven managed service platform targeting small organizations (1–40 users) in professional services, legal, accounting, and healthcare with FTC Safeguards Rule compliance as a core, bundled offering.

We are at a stage where consistent process, clear escalation paths, and structured vendor oversight will meaningfully separate good from great. This role is the linchpin of that development.

Role and Responsibilities

Essential duties and responsibilities include the following. Other duties may be assigned.

Technical Support & Escalation

  • Own L2/L3 escalations across the client base to assist with server, networking, Microsoft 365, Azure, and security stack
  • Serve as the primary escalation point for frontline technicians and outsourced NOC/helpdesk partners
  • Resolve complex technical issues with documented root cause analysis
  • Maintain hands-on proficiency with all platforms in the MSP stack

Process & Controls Development

  • Help build, maintain, and enforce standard operating procedures, runbooks, and escalation playbooksIdentify systemic service delivery gaps through ticket trend analysis and act on them
  • Drive adoption of documentation standards across the team (Hudu or equivalent)
  • Own the onboarding checklist and quality gate for new client environments
  • Working with the team to develop and implement automation and AI based runbooks to improve efficiency and heighten the client experience

Team Development & Collaboration

  • Mentor and develop frontline technicians via structured coaching, not just reactive feedback
  • Collaborate with leadership on tooling decisions around RMM, PSA, documentation and security platform strategy
  • Monitor open queues, SLA adherence, and resolution quality metrics; surface findings to leadership
  • Participate in client escalation calls as the senior technical voice when needed

Outsourced Team Management

  • Manage day-to-day performance of outsourced support partners to set expectations, review KPIs, and drive quality outcomes
  • Conduct regular performance reviews and QBR-style sessions with vendor teams
  • Identify and escalate gaps in outsourced delivery before they reach clients
Qualifications and Education Requirements

Required

  • 4+ years in a managed services environment with demonstrated L2/L3 technical depthExperience managing or coordinating teams such as NOC, offshore helpdesk, or vendor SOC
  • Proven track record building or formalizing service delivery processes and documentation
  • Proficiency with EDR/MDR platforms, particularly SentinelOne, CrowdStrike, or Huntress in a multi-tenant MSP deploymentProficiency with PSA platforms (HaloPSA, ConnectWise) and RMM tools (NinjaOne, Kaseya, Datto)
  • Proficiency with Email Security (e.g. Checkpoint Avanan, Proofpoint) and DNS Security (e.g. DNSFilter, Cisco Umbrella) toolsets
  • Proficiency with M365 and Azure environments, troubleshooting, standard setup, management of Exchange, Teams, Sharepoint, Intune and Entra ID
  • Windows Server administration proficiency in Active Directory, Group Policy, DNS/DHCP, Remote Desktop Services
  • Networking proficiency with TCP/IP, VLANs, routing, firewall management (Meraki, Fortinet, or similar)
  • Virtualization understanding of VMware or Hyper-V at an administrative level
  • Backup and DR experience with Datto, Veeam, or equivalent; validation and test restore discipline

Strongly Preferred

  • ITIL Foundations or equivalent service management framework exposure
  • HaloPSA hands-on experience in service delivery, workflow configuration, asset management, reporting
  • Background in building or improving onboarding and offboarding workflows for managed environments
  • Experience with AI workflow automation platforms (e.g., Rewst, n8n, Make, Power Automate) and using AI to reduce manual operational work
  • Experience with AI-native documentation or knowledge management platforms (e.g., Lexful.ai, IT Glue, Hudu)