ConnectWise Cloud Specialist (Remote)

Role Summary

GMI is seeking a Contract ConnectWise Cloud Specialist to administer, optimize, and support the company's ConnectWise environment. This individual will serve as the primary subject matter expert responsible for platform administration, workflow automation, ticket lifecycle management, agreement administration, reporting, integrations, and user adoption.

The ideal candidate brings deep hands-on experience with ConnectWise PSA/Cloud, understands MSP business processes, and can identify opportunities to improve operational efficiency across Service Delivery, Customer Success, Operations, Finance, and Sales.

Key Responsibilities

ConnectWise Administration

• Administer and maintain ConnectWise Cloud/PSA platform configurations.
• Create and manage service boards, statuses, workflows, ticket types, and security roles.
• Maintain system integrity, governance standards, and user permissions.
• Support system upgrades, enhancements, and platform optimization initiatives.
  
  

Workflow Optimization

• Analyze current business processes and recommend operational improvements.
• Automate repetitive tasks through workflows, notifications, and routing rules.
• Standardize ticketing, documentation, escalation, and service delivery processes.
• Improve technician efficiency and reporting accuracy.
  
  

Service Delivery Support

• Support service desk, managed services, and project operations workflows.
• Optimize ticket routing, dispatching, escalation paths, and SLA management.
• Assist departments with agreement setup, recurring billing structures, and contract administration.
• Monitor process adherence and recommend corrective actions when necessary.
  
  

Reporting & Analytics

• Develop operational dashboards and executive-level reporting.
• Build KPI reporting related to service performance, utilization, SLA attainment, backlog management, and operational efficiency.
• Analyze trends and provide recommendations for continuous improvement.
• Support leadership requests for reporting and business insights.
  
  

Data Quality & Governance

• Audit customer, agreement, service, and asset data for accuracy.
• Identify data inconsistencies and implement cleanup initiatives.
• Establish governance standards and documentation practices.
• Maintain platform documentation, SOPs, and process maps.
  
  

Training & Enablement

• Train new and existing users on ConnectWise best practices.
• Develop user guides and standard operating procedures.
• Serve as an internal subject matter expert for platform-related questions.
• Promote adoption of efficient workflows and business processes.
  
  

Integration Management

• Support integrations between ConnectWise and third-party business applications.
• Assist with API-based integrations and automation initiatives.
• Troubleshoot synchronization and workflow issues.
• Coordinate with vendors and internal stakeholders on enhancement requests.
  
  

Required Qualifications

• 3+ years of hands-on ConnectWise PSA / ConnectWise Cloud administration experience.
• Experience in an MSP, MSSP, VAR, or IT services organization.
• Strong knowledge of:
• Service Boards
• Ticketing workflows
• Agreements
• SLAs
• Dispatching
• Time entry management
• Reporting and dashboards
• Workflow rules and automation
• Experience supporting service delivery and operational teams.
• Strong analytical, organizational, and problem-solving skills.
• Advanced Microsoft Excel proficiency.
  

Preferred Qualifications

• ConnectWise Administrator certifications or equivalent experience.
• Experience with ConnectWise Asio.
• Experience with BrightGauge or Power BI.
• Understanding of MSP operational best practices.
• Exposure to cybersecurity, managed services, or professional services environments.
• Experience with API integrations and automation platforms.