Senior Desktop Support Analyst
About this role
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”.
#LI-DNI
Company at a glance
At Plymouth Rock Assurance, our employees and Independent Agents bring the mission of delivering exceptional and reliable service to customers across the Northeast to life. You’ll find a culture built on collaboration and curiosity, where dedicated employees take pride in helping others succeed.
We’re proud to be recognized as a 2025 Top Workplace in New Jersey by NJ Advance, in addition to being included in Forbes’ Best Insurance Companies 2026 list and earning top honors as the Best Car Insurance Company in Massachusetts of 2026 by The Wall Street Journal’s “Buy Side”. It’s a reflection of our people and to building a place where opportunity grows.
With offices in Woodbridge, New Jersey and Boston, Massachusetts, Plymouth Rock offers auto, home, renters, and condo insurance across New Jersey, New York, New Hampshire, Massachusetts, Connecticut, and Pennsylvania designed to protect what matters most. Our long-held commitment to high-quality service extends to giving back to the local communities we live and serve through volunteerism and the Plymouth Rock Assurance Foundation.
Interested in joining our team? View our employment opportunities: www.plymouthrock.com/about/careers.
Top Benefits
- Paid Time Off
- Paid National Holidays
- Free Onsite Gym
- Tuition Reimbursement
- Health Insurance
- Dental Insurance
- Vision Insurance
- Health And Wellness Program
- Fitness Reimbursements
- Auto Insurance Discounts
- Home Insurance Discounts
- Matching Gift Opportunities
- 401(k) Employer Contribution
- Paid Family Leave
- Paid Parental Leave
- Professional Development Resources
- Pre-Tax Commuter Benefits
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