Senior Desktop Support Analyst

plymouthrock; Boston (MA); Hybrid; USD 84,000 - 117,000; Full time

Benefits offered by this job

4 weeks PTO + 9 holidays

onsite gym

Tuition reimbursement

Health insurance from Day 1

401(k) matching

Paid family leave

Professional development support

Pre-Tax commuter benefits

South Station location

Job summary

The Plymouth Rock Company is seeking a Senior Desktop Support Analyst in Boston to manage and secure endpoints, deploy software, and provide tier 2/3 support. The role emphasizes customer service and collaboration within a dynamic IT team.

The position is based in Boston with a 4/1 in-office/remote schedule, 8:00am–4:00pm, and occasional travel/on-call support. Requires Windows/macOS expertise, Microsoft 365, AD, SCCM, Intune, and scripting knowledge.

Qualifications

• Windows and macOS familiarity with endpoint management.
• Strong troubleshooting and problem-solving abilities; good communication and teamwork.
• Basic networking and video conferencing understanding.
• ITIL certification and experience in IT support are beneficial.
• Bachelor’s degree in Computer Science, IT, or related field (or equivalent experience) required.

Responsibilities

• Deploy and maintain devices; patch OS and applications using Intune and Jamf.
• Collaborate with IT teams on software deployment and maintenance; assist with patch management and documentation.
• Provide user support, onboarding/offboarding, provisioning/deprovisioning of devices, and support video conferencing systems.

Skills

Windows

macOS

Microsoft 365

Active Directory

Group Policy

SCCM

Intune

Jamf

PowerShell

Python

ITIL

Education

Bachelor’s degree in CS/IT

Equivalent experience

Tools

Jamf Pro

Intune

SCCM

PowerShell

Job description

Senior Desktop Support Analyst

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.

About the Company

The Plymouth Rock Company and its affiliated group of companies write and manage over $2.2 billion in personal and commercial auto and homeowner’s insurance throughout the Northeast and mid-Atlantic, where we have built an unparalleled reputation for service. We continuously invest in technology, our employees thrive in our empowering environment, and our customers are among the most loyal in the industry. The Plymouth Rock group of companies employs more than 2,000 people and is headquartered in Boston, Massachusetts.Plymouth Rock Assurance Corporation holds an A.M. Best rating of “A-/Excellent”.

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