IT Help Desk Specialist — Windows, Mac & 365

Insight Global; Ipswich (MA); On-site; USD 41,000 - 69,000; Full time

Benefits offered by this job

Medical, dental, and vision coverage

401(k) after 90 days

Paid sick leave and PTO

Job summary

Insight Global is seeking an IT Helpdesk professional in Massachusetts to provide Tier 1/2 support for Windows and macOS users. You will handle incidents via FreshService, email, phone, or walk-up, troubleshoot hardware/software, and image/deploy endpoint devices for new hires and current staff.

Primary duties include supporting Microsoft 365 apps, documenting tickets, and escalating when needed. A strong communicator with experience in enterprise environments is preferred.

Qualifications

• 2+ years of hands-on IT Helpdesk or Deskside Support experience (enterprise environment preferred).
• Strong troubleshooting skills across Windows and macOS platforms.
• Experience supporting Microsoft 365 applications and user accounts.
• Familiarity with ticketing systems (FreshService, ServiceNow, Zendesk, or equivalent).
• Ability to diagnose basic networking and connectivity issues (Wi‑Fi, VPN, printing, peripherals).
• Strong written and verbal communication skills.
• Proven ability to manage multiple tickets and competing priorities - Experience with endpoint management tools (Intune, Jamf, or similar).
• Familiarity with Active Directory or Entra ID user/device management.
• Experience supporting conference room or AV technology and onboarding/offboarding workflows.

Responsibilities

• Provide Tier 1 / Tier 2 support for end users across Windows and macOS environments.
• Respond to incidents and service requests submitted via FreshService, email, phone, or walk-up support.
• Troubleshoot hardware and software issues, including laptops, peripherals, printers, and conference room equipment.
• Image, configure, deploy, and troubleshoot endpoint devices for new hires and existing employees.
• Support Microsoft 365 applications (Outlook, Teams, OneDrive, Office apps).
• Track, document, and update tickets clearly to ensure accurate communication and timely resolution.
• Escalate issues appropriately when root cause exceeds tiered support scope.
• Follow established IT processes, security guidelines, and documentation standards.
• Provide professional, courteous support to users at all technical skill levels.

Skills

IT Helpdesk

Troubleshooting

Microsoft 365

Ticketing systems

Networking basics

Communication

Endpoint management

AD / Entra ID

AV systems

Onboarding

Tools

FreshService

ServiceNow

Zendesk

Intune

Jamf

Entra ID

Job description

Insight Global is seeking an IT Helpdesk professional in Massachusetts to provide Tier 1/2 support for Windows and macOS users. You will handle incidents via FreshService, email, phone, or walk-up, troubleshoot hardware/software, and image/deploy endpoint devices for new hires and current staff.

Primary duties include supporting Microsoft 365 apps, documenting tickets, and escalating when needed. A strong communicator with experience in enterprise environments is preferred.