Senior IT Support Specialist

About the Role

We are seeking a highly skilled
Freelancer Senior IT Support Specialist
to provide advanced technical support, project assistance, and IT coverage for our client operations. This role ensures the continuity, efficiency, and security of client technology systems by resolving complex issues, supporting IT projects, and delivering exceptional service.

Initially, you will work onsite in
New York City two days per week
for knowledge transfer and cross-training with the existing team. Afterward, the role transitions to
as-needed support
for project work, PTO coverage, and specialized consultation.

Key Responsibilities

Technical Support & Service Delivery

• Serve as the primary escalation point for complex IT issues, including hardware, software, networks, and business systems.
• Provide both onsite and remote support to minimize downtime and maintain productivity.
• Troubleshoot Windows, macOS, Microsoft 365, cloud platforms, and network infrastructure.
• Support and maintain legal practice management systems such as
  LEAP
  , including setup, integrations, and user support.
• Collaborate with the IT Director and team to ensure efficient, scalable IT operations.

IT Projects & System Administration

• Lead or assist with infrastructure projects (network upgrades, migrations, system rollouts, security implementations).
• Evaluate IT environments, recommend improvements, and contribute to technology roadmaps.
• Manage system configurations, installations, and maintenance (Active Directory, DNS, DHCP, VPN, firewalls, servers).
• Coordinate with vendors to resolve escalated issues and project requirements.

Documentation & Process Management

• Maintain clear documentation: SOPs, configuration guides, and client-specific notes.
• Log all service activities in the ticketing system with detailed resolution notes.
• Support continuous improvement initiatives for IT processes, policies, and compliance.

Subject Matter Expertise & Training

• Act as an SME for
  LEAP
  and other critical platforms.
• Mentor junior IT staff and provide end-user training.
• Stay current with emerging technologies relevant to client operations.

Client Engagement & Professionalism

• Serve as a trusted technical advisor to clients.
• Communicate complex technical issues clearly to non-technical stakeholders.
• Maintain the highest standards of professionalism, responsiveness, and accountability.

Availability & Flexibility

• Onsite NYC presence required initially (2 days/week).
• Provide project-based support, PTO coverage, and urgent issue response as needed.

Qualifications

Education & Experience

• Bachelor's degree in IT, Computer Science, or related field (or equivalent experience).
• 6–8+ years of progressive IT support experience, including senior-level troubleshooting and client-facing service.
• Experience supporting legal practice management software (LEAP required).
• Professional certifications such as
  CompTIA A+
  ,
  Microsoft Certified Professional
  ,
  ITIL
  , or similar are highly valued.

Technical Expertise

• Advanced knowledge of Windows Server, Active Directory, Group Policy, DNS, DHCP, and networking (LAN/WAN, VPNs, firewalls).
• Experience with Microsoft 365, Google Workspace, Azure, and AWS.
• Familiarity with endpoint management, backups, VOIP, A/V conferencing, patch management, and security best practices.

Soft Skills

• Excellent client communication and interpersonal skills.
• Strong analytical and problem-solving abilities.
• Self-directed with the ability to manage priorities in a dynamic, project-based environment.
• High professionalism, discretion, and client empathy.

If you are a technically proficient, proactive, and client-focused IT specialist looking to provide strategic support in a professional services environment, we want to hear from you