Senior Desktop Support Analyst — Hybrid IT & Endpoint Expert

Plymouth Rock Assurance; Boston (MA); On-site; USD 83,500 - 117,000; Full time

Benefits offered by this job

4 weeks PTO + 9 holidays

Free onsite gym

Tuition reimbursement

Health insurance from day 1

401(k) matching up to 7.5%

Paid parental leave

LinkedIn Learning/licensure support

Pre-tax commuter benefits

Job summary

Plymouth Rock Assurance is hiring a Senior Desktop Support Analyst in Boston. The role focuses on tier 2/3 endpoint management, device deployment, patching, and user support in a collaborative IT environment.

Based in Boston with a 4-days-in-office, 1 remote schedule, this position requires strong customer service, technical hands-on skills, and willingness to travel occasionally. Competitive benefits accompany a comprehensive health plan and 401(k) program.

Qualifications

• Experience with Windows and macOS environments.
• Advanced knowledge of Microsoft 365 and Active Directory group policy management, SCCM and Intune.
• Strong troubleshooting and problem-solving abilities.
• Excellent communication and ability to work independently and in a team.
• Basic networking knowledge.
• ITIL certification and endpoint support experience are pluses.

Responsibilities

• Assist with deployment and maintenance of devices and patching.
• Collaborate with IT teams on software deployment and maintenance; assist with patch management.
• Provide user support, training on best practices, and onboarding/offboarding provisioning.

Skills

Troubleshooting

Teamwork

Customer service

Learning mindset

Education

B.S. in Computer Science or related field

ITIL certification (beneficial)

Tools

Intune

Jamf

SCCM

Active Directory

Microsoft 365

PowerShell

Python

Job description

Plymouth Rock Assurance is hiring a Senior Desktop Support Analyst in Boston. The role focuses on tier 2/3 endpoint management, device deployment, patching, and user support in a collaborative IT environment.

Based in Boston with a 4-days-in-office, 1 remote schedule, this position requires strong customer service, technical hands-on skills, and willingness to travel occasionally. Competitive benefits accompany a comprehensive health plan and 401(k) program.