Level III Help Desk Technician

Job Description

Job Description

Position Summary

Freedom Technology Solutions is seeking an experienced Level III Help Desk Technician to provide advanced technical support to our clients.

This position serves as a senior resource for the Help Desk and is responsible for resolving complex workstation, server, network, cloud, security, and Microsoft 365 issues. The technician will work directly with clients, junior technicians, Central Services, Professional Services, and Client Success to restore service, identify root causes, and improve the overall client technology experience.

The ideal candidate combines strong technical troubleshooting skills with excellent communication, documentation, organization, and customer service. This role requires someone who can independently manage complicated technical issues while knowing when to collaborate with other teams or escalate a problem.

Key Responsibilities

Advanced Technical Support

• Provide Level II and Level III remote technical support for managed clients.
• Troubleshoot and resolve complex hardware, software, operating system, network, cloud issues or move them to the appropriate team with adequate notes.
• Serve as a resource for less experienced Help Desk technicians.
• Diagnose recurring or high-impact technical problems and identify their underlying causes.
• Work incidents through completion while meeting established service-level requirements.
• Communicate clearly with clients throughout the troubleshooting and resolution process.
• Confirm that services are fully restored before closing tickets.
• Coordinate with vendors and third-party support providers when external assistance is required.

Microsoft and Cloud Support

• Administer and troubleshoot Microsoft 365 services, including:
• • Exchange Online
  • Outlook
  • Microsoft Teams
  • SharePoint
  • OneDrive
  • Entra ID
  • Intune
  • Microsoft Defender
• Troubleshoot identity, authentication, conditional access, licensing, mailbox, synchronization, and permissions issues.
• Understand Active Directory, Group Policy, DNS, DHCP, file shares, and Windows Server environments.
• Troubleshoot hybrid identity and directory synchronization issues.
• Assist with endpoint enrollment, configuration profiles, application deployment, and compliance policy adherence.
• Diagnose LAN, WAN, wireless, DNS, DHCP, routing, switching, firewall, and VPN issues.
• Troubleshoot site-to-site and remote-access VPN connectivity.
• Support WatchGuard firewalls.
• Review logs, alerts, packet behavior, and network configuration information to identify service disruptions.
• Assist with server outages, storage issues, failed services, authentication problems, and connectivity interruptions.
• Coordinate infrastructure changes with Professional Services and Central Services when appropriate for

Security and Compliance

• Investigate endpoint, email, identity, and network security alerts..
• Follow established identity-verification and authorization procedures before performing password resets, MFA changes, remote-access sessions, or other sensitive actions.
• Escalate suspected compromises, phishing events, unauthorized access, malware, and other security incidents immediately.
• Maintain confidentiality when working with client systems and information.
• Follow applicable security, privacy, and compliance requirements, including procedures used for HIPAA-regulated clients.
• Ensure security controls are not disabled or bypassed without documented authorization.

Ticket and Service Management

• Create, update, and maintain accurate service tickets in Autotask.
• Document:
• • Reported symptoms
  • Troubleshooting performed
  • Diagnostic results
  • Configuration changes
  • Client communications
  • Root cause
  • Final resolution
• Maintain ownership of assigned tickets and provide timely status updates.
• Prioritize work according to business impact, urgency, security risk, and service-level requirements.
• Identify tickets that require escalation, project work, onsite service, vendor involvement, or management review.
• Record time entries accurately and contemporaneously.
• Review ticket history and documentation before repeating troubleshooting already completed by another technician.
• Help reduce ticket re-openings by confirming that solutions are complete and clearly documented.

Team Leadership and Mentoring

• Provide technical guidance to Level I and Level II technicians.
• Assist team members with troubleshooting strategies and escalation decisions.
• Review escalated tickets for completeness and accuracy.
• Share technical knowledge, recurring issue patterns, and effective resolutions with the team.
• Contribute to internal documentation, troubleshooting guides, and standard operating procedures.
• Help identify training opportunities and knowledge gaps within the Help Desk.
• Maintain a professional and collaborative approach during high-pressure situations.
• Lead by example in customer service, accountability, documentation, and technical quality.

Proactive Improvement

• Identify recurring incidents that may indicate larger infrastructure, security, configuration, or training problems.
• Recommend permanent corrective actions instead of relying solely on temporary workarounds.
• Submit documentation updates when client systems, contacts, configurations, or procedures change.
• Identify opportunities for automation, standardization, and improved service delivery.
• Alert Client Success or leadership when a technical pattern may affect a client’s technology roadmap or business operations.
• Participate in internal service reviews, technical meetings, and process-improvement initiatives.

Required Qualifications

• Three or more years of experience providing Level II or Level III technical support.
• Previous experience working for a Managed Service Provider is strongly preferred.
• Strong knowledge of Windows 10 and Windows 11.
• Working knowledge of Windows Server environments.
• Strong Microsoft 365 administration and troubleshooting experience.
• Experience supporting Active Directory, Group Policy, DNS, DHCP, and file permissions.
• Experience troubleshooting business networks, firewalls, switches, wireless systems, and VPNs.
• Experience with endpoint management, remote monitoring, ticketing, and documentation platforms.
• Ability to troubleshoot complex technical issues independently.
• Ability to organize and manage multiple active tickets.
• Strong written and verbal communication skills.
• Ability to explain technical issues clearly to nontechnical users.
• Strong attention to detail and commitment to accurate documentation.
• Valid driver’s license and reliable transportation for onsite client visits.
• Ability to safely lift and transport computers, monitors, networking equipment, and related hardware.

Preferred Qualifications

Experience with one or more of the following is preferred:

• Autotask PSA
• Kaseya VSA or VSA X
• Microsoft Intune
• Microsoft Entra ID
• Microsoft Defender
• Azure virtual machines and networking
• WatchGuard firewalls
• Datto BCDR
• Datto networking equipment
• Duo Security
• RocketCyber or another managed SOC platform
• INKY or another email security platform
• IT Glue
• PowerShell
• Hyper-V or VMware
• Backup and disaster-recovery testing
• Cybersecurity incident response
• HIPAA-regulated client environments

Relevant Microsoft, CompTIA, Cisco, WatchGuard, Kaseya, or security certifications are beneficial but not required when equivalent professional experience can be demonstrated.

Technical Competencies

The successful candidate should be able to demonstrate proficiency in several of the following areas:

• Advanced Windows workstation troubleshooting
• Windows Server administration
• Microsoft 365 administration
• Exchange Online and Outlook troubleshooting
• Active Directory and Group Policy
• Entra ID and multifactor authentication
• Intune enrollment and policy troubleshooting
• DNS and DHCP
• TCP/IP networking
• VLANs, routing, switching, and wireless networking
• Firewall policies and VPN configurations
• File and share permissions
• Printer and application troubleshooting
• Virtualization
• Backup and recovery
• Endpoint security
• Email security
• PowerShell or command-line diagnostics
• Log review and root-cause analysis

Performance Expectations

Success in this position will be measured by:

• Timely and accurate ticket resolution
• Compliance with service-level requirements
• Quality and completeness of ticket documentation
• Client satisfaction and communication
• Reduction in repeat incidents and reopened tickets
• Appropriate escalation and ownership of complex issues
• Contribution to team knowledge and technician development
• Adherence to security and identity-verification procedures
• Accuracy of time entries and service records
• Ability to identify and resolve root causes
• Consistent demonstration of Freedom Tech’s core values

Schedule and Availability

• Full-time position based from Freedom Technology Solutions’ Johnston, Rhode Island office.
• Standard Help Desk coverage operates between 7:00 a.m. and 6:00 p.m. in 3 different shifts
• The assigned daily schedule will fall within the department’s coverage hours.
• Participation in the rotating after-hours support schedule will be required.
• Occasional evening or weekend work may be necessary for emergencies, maintenance, projects, or client-impacting incidents.
• Local travel to client locations throughout Southern New England may be required.

Core Values

All Freedom Tech team members are expected to consistently demonstrate:

• Great Attitude
• Improvement
• Above and Beyond
• Professionalism
• Teamwork
• Tenacity
• Confidence
• Rapport
• Work Ethic
• Care

About Freedom Technology Solutions

Founded in 2001, Freedom Technology Solutions is a Rhode Island-based technology services company supporting organizations throughout Southern New England and other parts of the country. Our team provides managed technology, cybersecurity, cloud, infrastructure, backup, and strategic technology services to a diverse client base.

We are continuing our evolution from a traditional Managed Service Provider into a Managed Intelligence Provider, combining experienced professionals, standardized operations, security, automation, and actionable business intelligence to help clients make better technology decisions.

Find Freedom.