Virtual Help Desk Jobs in Massachusetts (NOW HIRING)

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 escalate 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.