Senior IT Support Specialist, Legal Tech

Paragon Tech Inc. is seeking a Senior Legal Technology Support Specialist to serve as a primary support resource for our law firm clients. This role combines client support, legal technology troubleshooting, IT systems support, cybersecurity awareness, and operational ownership within a fast-growing legal technology company.

This is not an entry-level help desk role. We are looking for a highly self-sufficient, motivated, organized, and career-oriented individual who wants to grow long term with the company. The ideal candidate enjoys solving problems independently, learning quickly, improving systems, documenting processes, and delivering exceptional client experiences.

This position is heavily focused on supporting modern law firm environments, including legal technology platforms, Microsoft 365, Windows and Mac support, cybersecurity best practices, user administration, and troubleshooting across both legal and IT systems. The role also involves working closely with our Engineering and Supercharger teams to understand client configurations, workflows, implementations, and newly deployed systems.

The ideal candidate takes ownership, communicates professionally, follows through consistently, works efficiently under pressure, and thrives in a fast-paced environment where priorities can shift quickly based on client needs.

Responsibilities

• Review, manage, and prioritize incoming support tickets and escalations
• Respond to and resolve client support requests quickly and professionally
• Troubleshoot legal software platforms and related IT systems
• Support Microsoft 365 environments, user administration, email, security settings, and device troubleshooting
• Assist with cybersecurity implementations and security-related client changes
• Escalate advanced technical issues when appropriate while maintaining ownership of communication and follow-through
• Work directly with the Supercharger Team to understand client-specific workflows and newly implemented systems
• Create and maintain internal process documentation, support procedures, and knowledge base resources
• Assist with proactive improvements to client environments and internal support operations
• Communicate technical concepts clearly to both technical and non-technical users
• Manage multiple priorities and task-switch effectively in a fast-moving support environment
• Contribute to long-term client relationships, client satisfaction, and service team growth

Do you have experience in macOS?, * You are naturally curious and enjoy troubleshooting independently

• You are highly responsive, organized, and accountable
• You want to build a long-term career in IT, legal technology, cybersecurity, or systems consulting
• You care about delivering excellent client experiences
• You are comfortable being measured by responsiveness, follow-through, quality of work, and client satisfaction
• You can adapt quickly and handle shifting priorities
• You are self-motivated and continuously looking to improve
• You do not require constant supervision to stay productive
• You want to grow with a company where strong performance can create future opportunities, Paragon Tech is a supportive and growth-focused company, but this role requires consistent effort, accountability, and a genuine desire to improve. We move quickly, communicate directly, and expect team members to take ownership of their work. This is a strong opportunity for someone who wants to build a meaningful long-term career with us and make a real impact on our clients and service operations., * CompTIA A+ certification required
• Microsoft 365 experience required
• Strong troubleshooting and problem-solving skills
• Experience supporting Windows environments required
• Mac OS support experience preferred
• CompTIA Network+ or Security+ preferred
• Experience with legal technology platforms such as Clio, Lawmatics, Smokeball, or similar systems preferred
• Legal operations knowledge preferred
• MSP, help desk, or service desk experience preferred
• Ability to complete supported legal platform certifications within 3 months of hire, * Describe a technical issue you solved independently without escalation.
• Why are you interested in working in legal technology and IT support long term?
• Are you comfortable working in a fast-paced environment that requires multitasking and rapid task switching?
• Have you worked with legal software platforms such as Clio, Lawmatics, Smokeball, Microsoft 365, or similar systems?
• This role requires strong self-management and accountability while working independently. Are you comfortable operating with minimal supervision?

Experience:

• IT support: 2 years (Required)
• Microsoft 365: 1 year (Required)
• Customer support: 2 years (Required)
• Windows: 2 years (Required)
• macOS: 1 year (Preferred)

License/Certification:

• CompTIA A+ (Required)
• CompTIA Network+ (Preferred)
• CompTIA Security+ (Preferred)

Work Location: Hybrid remote in New Lenox, IL 60451

Pulled from the full job description

• Professional development assistance
• Health insurance
• Retirement plan
• Paid time off
• Employee discount
• Vision insurance
• Dental insurance, * Health insurance
• Dental insurance
• Vision insurance
• Paid time off
• Retirement plan
• Employee discount
• Professional development assistance

Job Type: Full-time

Pay: $50,000.00 - $70,000.00 per year, * Dental insurance

• Employee discount
• Health insurance
• Paid time off
• Professional development assistance
• Retirement plan
• Vision insurance