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Role Overview
This role serves as a technical specialist responsible for comprehensive client onboarding and Tier 2 service desk support. The position requires deep technical knowledge of infrastructure, networking, server environments, and Microsoft 365 ecosystems. You will conduct thorough technical assessments of new client environments, perform hands-on migration and deployment activities, and ensure seamless transitions during the onboarding process.
This is a customer-facing technical role that combines advanced troubleshooting capabilities with project coordination skills. You must excel at both independent on-site work and remote collaboration with internal technical teams.
Key Responsibilities: Client Onboarding & Technical Assessment (Primary Focus)
· Travel to new client sites to conduct comprehensive infrastructure assessments
· Perform deep-dive discovery of server environments (physical and virtual)
· Document network topology, switching, routing, firewall configurations, and VPN infrastructure
· Assess Active Directory structure, GPOs, user/group organization, and security posture
· Evaluate Microsoft 365 tenant configuration, licensing, and migration readiness
· Complete workstation and mobile device inventory with hardware specifications
· Deploy and configure Datto RMM agents and validate monitoring coverage
· Execute device provisioning, user account creation, and access validation per project plans
· Perform user training on new systems, security protocols, and support processes
· Create detailed environment documentation, asset inventories, and network diagrams
· Coordinate technical handoffs to Service Desk, vCIO, and Projects teams
· Follow onboarding checklists and SOPs while adapting to unique client environments
Tier 2 Service Desk Support (when not onboarding)
· Handle escalated technical issues requiring advanced troubleshooting
· Diagnose and resolve complex Windows Server, Active Directory, and network connectivity issues
· Troubleshoot Microsoft 365 administration problems (Exchange Online, SharePoint, Teams)
· Perform server patch management, monitoring, and performance analysis using Datto RMM
· Configure and troubleshoot VPN connections, DNS issues, and network routing problems
· Create and update technical documentation in HaloPSA knowledge base
· Mentor Tier 1 technicians and provide technical guidance
· Participate in after-hours emergency support rotation as needed
· Maintain accurate ticket documentation with root cause analysis
Required Qualifications: Technical Skills
· Strong understanding of networking fundamentals: TCP/IP, DNS, DHCP, VLANs, routing, switching
· Advanced knowledge of Windows Server (2012 R2 through 2022): AD, DNS, DHCP, file services, GPO
· Expertise with Active Directory: user/group management, OU structure, security groups, troubleshooting
· Proficiency in Microsoft 365 administration: Exchange Online, SharePoint, Teams, Intune
· Experience with server monitoring and RMM tools (Datto RMM preferred)
· Solid understanding of network security: firewalls, VPNs, security best practices
· Experience with PSA/ticketing systems (HaloPSA preferred)
· Ability to read and create network diagrams and technical documentation
· Understanding of backup/disaster recovery concepts and validation
Professional Skills
· Minimum 3-5 years of IT support experience in an MSP or enterprise environment
· Proven experience with client onboarding, migrations, or infrastructure projects
· Exceptional customer service and communication skills (written and verbal)
· Strong project coordination and time management abilities
· High attention to detail with process-oriented mindset
· Ability to work independently in client environments with minimal supervision
· Professional demeanor and appearance for client-facing interactions
· Valid driver's license and reliable transportation (REQUIRED - travel is essential to this role)
· Ability to lift and transport IT equipment (up to 50 lbs)
· Comfortable with 20% overnight travel (advance notice provided)
Preferred Qualifications
· Experience with Google Workspace administration
· Familiarity with Apple/macOS device management and support
· Knowledge of VMware or Hyper-V virtualization platforms
· Experience with cloud infrastructure (Azure, AWS)
· Certifications: Microsoft certifications (MS-900, MS-102, MD-102), Network+, CCNA, or equivalent
· Experience with Datto products (RMM, BCDR, Networking)
· Scripting experience (PowerShell preferred)
· ITIL Foundation or equivalent process framework knowledge
Technical Environment You'll Work With
· PSA: HaloPSA
· RMM: Datto RMM
· Microsoft 365 (Exchange Online, SharePoint, Teams, Intune)
· Active Directory and Azure AD
· Windows Server (2012 R2 - 2022)
· Various networking equipment (firewalls, switches, access points)
· Google Workspace (secondary)
· Apple ecosystem (secondary)
Performance Expectations
· Complete thorough, accurate technical assessments during client onboarding engagements
· Produce high-quality documentation including network diagrams, asset inventories, and environment notes
· Successfully execute onboarding projects on time and within scope
· Maintain professional client relationships and represent company values on-site
· Demonstrate technical expertise that builds client confidence
· Follow established processes while exercising sound technical judgment
· Collaborate effectively with internal teams for seamless client handoffs
· Continuously expand technical knowledge and stay current with technology trends
· Meet or exceed ticket resolution and customer satisfaction metrics for Tier 2 support
What We Offer
Join a leading, vision-oriented, energetic team dedicated to delivering second-to-none IT services. We offer outstanding, comprehensive benefits and a supportive work environment where your technical expertise and professional growth are valued.
What Makes You Successful in This Role
· You enjoy solving complex technical problems and explaining solutions clearly
· You're energized by visiting client sites and building relationships
· You take pride in creating thorough, organized documentation
· You're comfortable being the "technical expert in the room" during client meetings
· You balance following procedures with adapting to unique situations
· You communicate proactively about project status and technical findings
· You view travel as an opportunity rather than a burden
Pay: $49,000.00 - $65,000.00 per year
Benefits:
Work Location: Remote
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