Level II Helpdesk Technician -

Technology Services Location:

Milford, MA Salary:

$60,000-$75,000 annually

Employment Type:

Full-Time, Non-Exempt Search:

Confidential About the Opportunity A growing technology services organization is seeking an experienced Level II Helpdesk Technician to join its technical support team in Milford, MA. This position serves as an advanced technical resource responsible for independently troubleshooting and resolving Level II issues escalated from Tier I support. The role supports hardware, software, Microsoft environments, networking, endpoints, remote access, and local server operations across internal and client environments. The Level II Helpdesk Technician will also provide guidance to Level I technicians, maintain technical documentation, and escalate complex issues to senior technical or engineering resources when appropriate. Key Responsibilities Independently troubleshoot and resolve Level II technical issues escalated from Tier I support. Apply advanced diagnostic methods and root-cause analysis to hardware, software, network, and connectivity issues. Provide Tier II support for user accounts, system access, application errors, and endpoint configuration. Support Windows operating systems, Microsoft 365, and common business applications. Assist with network infrastructure, printers, remote access, and local server operations. Install, configure, maintain, and troubleshoot desktops, laptops, printers, peripherals, and other IT equipment. Support both remote and onsite users. Manage multiple support requests while meeting established service-level expectations. Document troubleshooting steps, resolutions, recurring issues, and technical best practices. Mentor Level I technicians and provide troubleshooting guidance and knowledge sharing. Follow established IT security policies, protocols, and best practices. Escalate critical or unresolved issues to Level III or engineering resources when appropriate. Assist with hardware inventory, equipment deployment, and asset management. These responsibilities closely track the attached internal JD.

Qualifications Required:

2-4 years of professional helpdesk, service desk, or IT support experience. Strong working knowledge of Windows operating systems, Microsoft 365, common business applications, and remote support tools. Experience troubleshooting hardware, software, applications, peripherals, and connectivity issues. Familiarity with networking concepts, including IP, DNS, and DHCP. Hands-on experience with hardware repair, peripheral installation, and endpoint deployment. Strong communication and customer service skills. Ability to work independently, manage multiple tickets simultaneously, and prioritize effectively. Commitment to continued technical learning and development. CompTIA A+ or similar foundational IT certification. Equivalent combinations of education and relevant experience will be considered.

Preferred:

Experience supporting users in a Managed Service Provider (MSP) environment. CompTIA Network+ or relevant Microsoft certification. These qualifications reflect the requirements and preferences in the attached JD. Work Environment This position is based in Milford, MA and requires regular onsite presence. Occasional travel to local client locations may be required. The position involves prolonged periods working at a computer and requires the ability to lift and carry equipment weighing up to 35 pounds. Compensation The anticipated base compensation range is $60,000-$75,000 annually , based on experience, technical capabilities, certifications, and overall qualifications. This position is non-exempt and eligible for overtime compensation in accordance with applicable federal and Massachusetts wage and hour requirements. What Success Looks Like The successful candidate will be expected to establish strong working relationships with the technical team, actively participate in training and knowledge transfer, ask questions when needed, and progressively take ownership of Level II support responsibilities. Why Join? This is an opportunity to join a growing technology services environment where you'll work across a broad range of technical issues rather than being limited to basic Tier I support. You'll collaborate with experienced technical professionals, gain exposure to networking and infrastructure issues, and continue building your technical skill set.

Confidential Search:

The employer's identity and additional information regarding the organization, benefits, team structure, and position will be shared with qualified candidates as they progress through the recruiting process.

Pay:

$60,000.00 - $75,000.00 per year

Benefits:

Flexible schedule Paid time off

Experience:

helpdesk, service desk, or IT support experience.: 2 years (Required)

Language:

English (Required)

License/Certification:

CompTIA A+ (Required)

Location:

Milford, MA 01757 (Preferred) Ability to

Commute:

Milford, MA 01757 (Required) Willingness to travel: 25% (Required)

Work Location:

In person