Senior Desktop Support Analyst

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

The Senior Desktop Support Analyst supports the IT team by providing tier 2/3 support in managing, maintaining, and securing an organization's endpoints, such as laptops, desktops, and mobile devices. This includes device management, software deployments, and user support. The ideal candidate is technically inclined, eager to learn, and able to work collaboratively within a dynamic IT environment. They should have a strong focus on customer service and operational excellence.

Office location and hours

This position is based in Boston Massachusetts, currently 4 days in the office and 1 remote workday. Hours are 8:00am – 4:00pm. Availability for occasional travel and on-call support is essential.

Responsibilities

• Responsibilities include assisting with the deployment and maintenance of various devices, managing OS and application patching using tools like Intune and Jamf, monitoring endpoint security, and troubleshooting hardware and software issues.
• Collaboration with IT teams on software deployment and maintenance, assist with patch management, maintain documentation, and provide user support and training on best practices.
• Assist with onboarding/offboarding processes, ensuring timely provisioning and deprovisioning of devices. Support video conferencing systems and remote access tools.

Qualifications

• Required skills include familiarity with Windows and macOS. Advanced knowledge of Microsoft 365 and Active directory group policy management as well as SCCM and Intune.
• Must have strong troubleshooting and problem-solving abilities, excellent communication, ability to work independently and in a team, and eagerness to learn new technologies.
• Basic understanding of networking and video conferencing technologies.
• Preferred qualifications include experience with endpoint management tools such Jamf, and familiarity with scripting languages like PowerShell or Python, information technology service management and basic knowledge of networking and video conference support.
• A Bachelor's degree in Computer Science, IT, or a related field (or equivalent experience) is required. ITIL certification and experience in IT support or a similar endpoint support role is also beneficial.

Perks and Benefits

• 4 weeks accrued paid time off + 9 paid national holidays per year
• Free onsite gym at our Boston Location
• Tuition Reimbursement
• Low cost and excellent coverage health insurance options that start on Day 1 (medical, dental, vision)
• Robust health and wellness program and fitness reimbursements
• Auto and home insurance discounts
• Matching gift opportunities
• Annual 401(k) Employer Contribution (up to 7.5% of your base salary)
• Various Paid Family leave options including Paid Parental Leave
• Resources to promote Professional Development (LinkedIn Learning and licensure assistance)
• Convenient location directly across from South Station and Pre-Tax Commuter Benefits

Salary Range: $83,500 to $117,000 per year. Actual compensation will vary based on multiple factors, including employee knowledge and experience, role scope, business needs, geographical location, and internal equity.