Senior IT Support Specialist

XS Brokers Insurance Agency Inc; Quincy (MA); On-site; USD 82,000 - 90,000; Full time

Job summary

XS Brokers Insurance Agency Inc. is seeking a Senior IT Support Specialist to serve as an escalation resource for the IT Service Desk. You will handle Level 2 incidents, perform advanced troubleshooting across Windows, M365, networking, and apps, and mentor junior staff.

This role bridges frontline support with infrastructure and security teams in a dynamic enterprise IT environment. You will administer NinjaOne and Intune, manage Entra ID/AD, and support VPN and VDI.

Qualifications

• Bachelor's degree in IT, Computer Science, or related field (or equivalent experience).
• 3–5 years of IT support experience with advancement from basic to complex work.
• Proficient in Windows OS, Microsoft 365, and AD/Entra ID administration.
• Hands-on experience with NinjaOne (RMM) and Freshservice (ITSM).
• Experience with Microsoft Intune for endpoint management.
• Knowledge of FortiClient/FortiSASE VPN configuration and support.
• Experience with VDI environments.
• Familiarity with Veeam backup platform at an operational level.
• Knowledge of ITIL processes; certifications preferred.

Responsibilities

• Receive and resolve escalated Level 2 incidents from Tier 1 with closure accountability.
• Troubleshoot across Windows OS, Microsoft 365, networking, VPN, and apps.
• Escalate to infrastructure, security, or vendors with thorough handoff docs.
• Identify patterns for root cause analysis.
• Administer NinjaOne RMM including remote remediation and patching.
• Manage Intune policies, device enrollment, and security configurations.
• Manage AD/Entra ID users, groups, and RBAC.
• Support Conditional Access and MFA in Entra ID.
• Manage VPN provisioning and connectivity in FortiClient/FortiSASE.
• Provide Level 2 support for VDI environments.
• Troubleshoot business apps like Vertafore AIM, Salesforce, Microsoft 365 services.
• Coordinate with vendors on escalated app incidents.
• Handle complex identity provisioning and access management.
• Review onboarding/offboarding workflows and runbooks.
• Ensure changes are documented for audits.
• Lead onboarding sessions ensuring workstation setup and app access.
• Monitor Veeam backup jobs and report issues.
• Support basic infrastructure health monitoring (Zabbix).
• Assist with patch management and vulnerability tracking.
• Maintain asset records for endpoints in ITSM.
• Lead IT projects and drive root-cause analysis to resolution.
• Develop and improve Freshservice knowledge base and runbooks.
• Contribute in team meetings and knowledge-sharing.

Skills

Advanced troubleshooting

Root cause analysis

Technical documentation

Self-directed ownership

Clear communication

Mentoring junior staff

Multi-tasking

Education

Bachelor's degree in IT or related field

Tools

NinjaOne

Freshservice

Microsoft Intune

Entra ID

Active Directory

FortiClient/FortiSASE

Veeam

VDI

Job description

Description

The Senior IT Support Specialist serves as an escalation resource for the IT Service Desk at XS Brokers Insurance Agency. This role handles escalated incidents from the Help Desk, delivers advanced troubleshooting across endpoints, identity, networking, and application layers, and actively participates in IT projects and continuous improvement initiatives. Operating with greater autonomy than Tier 1 staff, the Senior Specialist provides informal mentoring and technical guidance to junior team members and acts as a key bridge between frontline service desk operations and the infrastructure and security teams. This role is well suited for an experienced technician ready to deepen their enterprise IT expertise and take on broader organizational responsibilities.

Key Responsibilities

Advanced Technical Support & Escalation

• Receive, own, and resolve escalated Level 2 incidents from Tier 1 staff with full accountability through closure.
• Perform advanced troubleshooting across Windows OS, Microsoft 365, networking, VPN, and business application layers.
• Escalate to infrastructure, security, or vendor teams when appropriate, providing thorough handoff documentation.
• Identify patterns in escalated tickets and flag recurring issues for root cause analysis.

Endpoint & Identity Management

• Administer NinjaOne (RMM) including remote remediation, scripting, patching, and compliance monitoring.
• Manage Microsoft Intune policies, device enrollment, compliance baselines, and security configurations.
• Administer users, groups, and RBAC assignments in Active Directory and Entra ID.
• Support Conditional Access policy troubleshooting and MFA resolution in Entra ID.
• Manage FortiClient/FortiSASE VPN user provisioning, profile configuration, and connectivity troubleshooting.

VDI & Business Application Support

• Provide Level 2 support for Virtual Desktop Infrastructure (VDI) environments including connectivity, profile, and performance issues.
• Troubleshoot and support business applications including Vertafore AIM, Salesforce, and Microsoft 365 advanced services.
• Coordinate with application vendors on escalated application-layer incidents.

Onboarding & Offboarding (Advanced)

• Handle complex identity provisioning, RBAC access grants and revocations, and security-aligned access management.
• Review and maintain onboarding/offboarding workflows, runbooks, and Freshservice automations.
• Ensure access changes are accurately executed and documented to support audit and compliance requirements.
• Lead onboarding sessions ensuring that customers have setup their workstation successfully and have access to all associated applications required for their role.

Backup Awareness & Infrastructure Support

• Monitor Veeam backup job status and elevate failures or anomalies to the infrastructure team promptly.
• Support basic infrastructure health monitoring (Zabbix or equivalent) and report anomalies as needed.
• Assist with patch management cycles and vulnerability remediation tracking in NinjaOne and Intune.

Asset Management

• Maintain and deploy laptops and peripherals to onsite and remote customer base.
• Diagnose/repair hardware issues, configure laptops, and work with new hires to remotely perform initial setups.
• Maintain accurate asset records for assigned endpoints in ITSM platform.
• Assist in site asset audits and eWaste scheduling.

Projects & Continuous Improvement

• Participate in IT projects, rollouts, and implementation activities as assigned by the Help Desk Manager.
• Lead root cause analysis on recurring Tier 1 and Tier 2 incidents and drive resolution to completion.
• Develop, maintain, and improve Freshservice knowledge base articles, runbooks, and process documentation.
• Recommend tooling or process improvements to increase service desk efficiency and reduce escalation volume.

Mentoring & Team Contribution

• Provide informal technical guidance and mentoring to Tier 1 (Associate IT Support Analyst) staff.
• Review complex escalations with Tier 1 to reinforce troubleshooting skills and reduce repeat escalations.
• Contribute to team meetings, service reviews, and knowledge-sharing sessions.

Requirements

Qualifications

• Bachelor's degree in IT, Computer Science, or a related field (or equivalent experience with demonstrated progression).
• 3–5 years of IT support experience with clear advancement from basic to complex technical work.
• Proficient in Windows OS, Microsoft 365, and Active Directory/Entra ID administration.
• Hands-on experience with NinjaOne (RMM) and Freshservice or an equivalent ITSM platform.
• Demonstrated experience with Microsoft Intune for endpoint management and policy administration.
• Working knowledge of FortiClient/FortiSASE VPN configuration and end-user troubleshooting.
• Experience supporting Virtual Desktop Infrastructure (VDI) environments.
• Familiarity with Veeam or equivalent backup platform at an operational monitoring level.
• Working understanding of ITIL-aligned processes: Incident, Problem, and Change Management.
• CompTIA Network+, Microsoft 365 Certified (MD-102 or equivalent), or similar certification preferred.
• ITIL Foundation certification a plus.

Key Competencies

• Advanced troubleshooting and root cause analysis skills across hardware, OS, identity, and network layers.
• Clear, consistent technical documentation habits — detail-oriented without prompting.
• Self-directed with strong ownership and follow-through on open and complex issues.
• Able to communicate technical problems and resolutions clearly to non-technical stakeholders.
• Collaborative team contributor who can guide junior staff without formal authority
• Adaptable and effective when managing multiple concurrent complex escalations

Salary range for this role is $82,000-$90,000.