Remote IT Support Specialist - L3

About us

LifeMD is a leader in virtual primary care, headquartered in NYC, and we're redefining how healthcare meets technology. Our vertically integrated digital care platform powers telemedicine, laboratory services, and pharmacy solutions, serving over 200 conditions across all 50 states.

At the heart of this transformation is our team of 50+ talented developers, engineers, and tech innovators building state-of-the-art systems that make healthcare smarter, faster, and more accessible. From architecting scalable backend systems to crafting intuitive user experiences, we are pushing boundaries every day.

Recognized as one of the fastest-growing healthcare tech companies (#166 on Deloitte Fast 500 in 2023), LifeMD is not just a healthcare company—it’s a tech company revolutionizing healthcare.

If you're passionate about building impactful technology, solving complex challenges, and seeing your code change lives, LifeMD is the place to grow, innovate, and make a difference.

Join us and let's build the future of healthcare—together. 🚀

About the role

LifeMD is seeking an experienced IT Support Specialist, Level 3 to join our Information Technology team. In this role you will serve as the highest tier of internal technical support, acting as the final escalation point for complex and critical incidents that Level 1 and Level 2 support cannot resolve. You will bring deep expertise in enterprise networking, infrastructure, cloud platforms, identity systems, and security operations.

In addition to core L3 support responsibilities, you will serve as LifeMD’s primary Jira administrator, owning the configuration, governance, and ongoing optimization of Jira Software and Jira Service Management. You will partner closely with engineering, security, and operations leadership to maintain system reliability and compliance across LifeMD’s telehealth platform.

Core Responsibilities:

• Advanced Technical Support & Incident Resolution: Serve as the final escalation point for complex issues from L1 and L2 support teams, owning expert-level diagnosis and resolution through to closure. Investigate and resolve critical incidents spanning IT infrastructure, enterprise networking, cloud platforms (AWS), enterprise applications, and security systems. Lead root cause analysis for major incidents, producing post-incident reports with corrective action plans. Participate in on-call rotations for Severity 1 and Severity 2 incidents outside of standard business hours.
• Advanced Network Troubleshooting: Perform in-depth network diagnostics including packet capture and protocol analysis (Wireshark or equivalent), routing and switching diagnostics (BGP, OSPF, VLANs, spanning tree), firewall rule review, VPN connectivity failures, and DNS/DHCP resolution issues.
• Systems Administration & Infrastructure Support: Administer and support enterprise IT systems including identity platforms (Active Directory, Okta), endpoint management (MDM), and SaaS applications. Manage and troubleshoot complex networking issues at an infrastructure level. Support AWS cloud infrastructure including EC2, S3, IAM, and CloudWatch. Coordinate with Information Security on vulnerability remediation, access control reviews, and security incident response.
• Jira Administration: Serve as LifeMD’s primary Jira administrator, owning configuration, governance, and ongoing optimization of Jira Software and Jira Service Management. Design and manage projects, boards, workflows, permission schemes, and issue type configurations. Build and maintain automation rules, administer user access controls, manage integrations with Confluence, Slack, and GitHub, and develop dashboards and reports providing visibility into SLA compliance and incident trends. Evaluate and deploy plugins and marketplace apps; maintain governance documentation aligned with ITIL best practices.
• Process Improvement & Documentation: Identify systemic gaps in support operations and translate findings into actionable process improvements. Develop and maintain knowledge base articles, runbooks, and SOPs for L1 and L2 teams. Contribute to ITSM process development — incident, change, and problem management — in alignment with ITIL standards.
• Stakeholder Communication & Collaboration: Communicate proactively with end users, IT leadership, and cross-functional stakeholders on incident status, resolution timelines, and planned maintenance. Partner with IT leadership to ensure Jira configuration and ITSM tooling stay aligned with organizational governance objectives.

Basic Qualifications:

• Technical Skills:
• Advanced network troubleshooting proficiency: packet capture and protocol analysis, routing and switching diagnostics (BGP, OSPF, VLANs, spanning tree), firewall rule analysis, VPN diagnostics, DNS/DHCP failure resolution.
• Strong knowledge of enterprise IT infrastructure including identity platforms (Active Directory, Okta), endpoint management, and cloud platforms (AWS preferred).
• Expert-level Jira administration (Jira Software and Jira Service Management), including workflows, permission schemes, automation rules, and integrations. Atlassian certifications (ACP-120, ACP-420, or equivalent) strongly preferred.
• Experience with ITSM frameworks and best practices, particularly ITIL (Foundation certification preferred).
• Scripting proficiency in Python, PowerShell, or Bash for systems administration and automation tasks.
• Hands-on experience with AWS services including EC2, S3, IAM, and CloudWatch.
• Familiarity with CI/CD pipelines, GitHub, and DevOps toolchains as they relate to IT support handoffs.
• Familiarity with AI-assisted IT operations tools is an advantage.
• Prior experience in healthcare IT or a regulated industry; familiarity with HIPAA compliance requirements is a plus.

• Soft Skills:
• Structured, methodical approach to diagnosis and problem-solving under pressure.
• Strong written and verbal communication skills with the ability to explain complex technical concepts to non-technical stakeholders.
• Ability to manage multiple high-priority incidents simultaneously without losing resolution quality.
• High sense of ownership, accountability, and proactive follow-through.
• Collaborative mindset with the ability to work across engineering, security, and operations functions.
• Customer-centric approach with a genuine commitment to end-user experience.

• Experience and Qualifications:
• Bachelor’s degree in Computer Science, Information Technology, or a related field, or equivalent practical experience.
• Minimum 5 years of progressive IT support experience, with at least 2 years in an L3 or senior IT support capacity.
• Minimum 2 years of hands-on Jira administration experience in an enterprise environment.
• Atlassian certifications (ACP-120, ACP-420, or equivalent) strongly preferred.
• ITIL Foundation certification preferred; advanced ITIL certifications a plus.
• Salary Range: $80,000-$100,000
• Health Care Plan (Medical, Dental & Vision)
• Retirement Plan (Roth 401k)
• Life Insurance (Basic, Voluntary & AD&D)
• Unlimited PTO Policy
• Paid Holidays
• Short Term & Long Term Disability
• Training & Development