IT Helpdesk and Field Service Engineer - Level 2.5-3

We are looking for a sharp, customer-focused IT Engineer to join our team on a part-time basis (3 days per week), with the opportunity to transition into a full-time role as the position grows. This is a hybrid role combining remote helpdesk support with scheduled on-site visits to client locations. You will serve as a go-to escalation point for complex issues and also contribute to ongoing IT projects alongside day-to-day support., Helpdesk & Support

• Provide Tier 2/2.5 technical support to end users via remote helpdesk and on-site visits
• Troubleshoot hardware, software, networking, and cloud-related issues
• Serve as an escalation point for Tier 1 technicians on complex or unresolved tickets
• Document all support activity accurately in the ticketing system
• Follow up with clients to ensure satisfaction and issue resolution

Microsoft Cloud & Infrastructure

• Administer and support Microsoft 365 (Exchange Online, Teams, SharePoint, OneDrive, Intune)
• Manage Azure Active Directory / Entra ID - users, groups, MFA, Conditional Access
• Support Microsoft Endpoint Manager (Intune) for device enrollment and policy management
• Administer Microsoft Defender, Purview, and related security toolsets
• Assist with Azure infrastructure tasks (VMs, storage, networking, backup)

VoIP & Telephony

• Configure, troubleshoot, and support RingCentral and Intermedia Elevate phone systems
• Provision and manage handsets, softphones, call queues, auto-attendants, and call routing
• Onboard and offboard users across VoIP platforms including number porting and license management
• Diagnose call quality issues (jitter, latency, packet loss) and coordinate with carriers or vendors as needed

On-Premises Infrastructure

• Administer on-premises Active Directory - user/group management, GPO creation and troubleshooting, OU structure
• Manage on-prem file servers, print servers, and shared resources
• Support hybrid AD environments including AD Connect / Entra Connect sync
• Assist with server maintenance, patching, and monitoring for Windows Server environments
• Support Datto backup appliances - verify backup jobs, perform test restores, and respond to alerts

Networking

• Configure and troubleshoot routers, managed switches, firewalls, and wireless access points
• Strong understanding of TCP/IP, DNS, DHCP, VLANs, and subnetting
• Assist with site-to-site VPN setup and remote access (SSL VPN, client-based)
• Perform network documentation including diagrams, IP addressing, and hardware inventories

On-Site Support

• Perform scheduled and emergency on-site visits to client locations
• Assist with workstation setup, hardware refreshes, and peripheral configuration
• Cable management, rack installation, and physical infrastructure support as needed

Projects & Collaboration

• Participate in IT projects including migrations, deployments, and system upgrades
• Collaborate with the project team to meet milestones and deliverables
• Create and maintain technical documentation, SOPs, and knowledge base articles

Do you have a valid Driver’s License license?, Do you have experience in Wireless networking?, You must have a dedicated car and will be compensated on travel to customers.

Must live 20-30 minutes from the Greenwich CT area as equipment will need to be picked up when needed and delivered to customer., * 3+ years of experience in IT support or a managed services environment

• Strong working knowledge of the Microsoft 365 ecosystem and Azure cloud services
• Hands-on experience with on-premises Active Directory - GPOs, user management, hybrid sync
• Solid networking fundamentals: TCP/IP, DNS, DHCP, VLANs, subnetting, firewalls, and wireless
• Experience with RingCentral and/or Intermedia Elevate - provisioning, administration, and troubleshooting
• Familiarity with Datto backup and disaster recovery appliances
• Experience working within Autotask PSA for ticketing, time entry, and task management
• Experience with Azure Active Directory / Entra ID and endpoint management (Intune or similar)
• Excellent written and verbal communication skills - confident with clients at all levels
• Ability to explain technical concepts clearly to non-technical users
• Comfortable working independently, managing time across remote and on-site environments
• Valid driver’s license and reliable transportation for client visits, * Microsoft certifications (MS-900, AZ-900, MD-102, MS-102, or higher)
• Experience in an MSP (Managed Service Provider) environment
• Advanced Autotask experience - workflows, reporting, or project tracking
• RingCentral Admin Portal certification or advanced admin experience
• Intermedia Elevate administration and hosted PBX experience
• Experience with Datto BCDR appliance management, Datto RMM, or Datto Networking
• CompTIA A+, Network+, or Security+ certifications
• Familiarity with ITIL practices or service desk frameworks
• Windows Server administration (2016/2019/2022) and Hyper-V or VMware experience, * Technical support: 4 years (Required)

$28 - $40 an hour - Full-time, Pulled from the full job description

• Flexible schedule, Hourly

  $28-$40/hr depending on experience, * Flexible part-time schedule - 3 days per week to start

• Clear pathway to a full-time role as you grow with the team
• Work-from-home flexibility with a supportive team environment
• Exposure to a wide variety of technologies and client environments
• Opportunity to contribute to meaningful projects alongside helpdesk work