Senior Technical Lead – Healthcare MSP

OCS IT is an award-winning managed IT and cybersecurity company in Cape Coral. We've been in business 18 years, and most of our clients are medical practices. When a practice's network, phones, or Microsoft 365 goes down, patients wait. Our clients count on fast answers from engineers who know their environment.

We're hiring a Senior Technical Lead to be the top escalation point on our service desk. You'll take the problems nobody else could solve. You'll also lead client projects and mentor the rest of the team.

What you'll work on:

• On-prem Active Directory, Group Policy, DNS and DHCP, including older servers still running in client offices. Domain controller upgrades and file server migrations.
• Microsoft 365 and Entra ID administration, including Intune, Conditional Access, Entra Connect, and tenant and mailbox migrations.
• Firewalls, HA pairs, and site-to-site IPsec tunnels, sometimes between different vendors. FortiGate experience is a plus.
• VLANs, routing, QoS and wireless, and tracking down the root cause of complex network problems.
• FreePBX, Sangoma and Switchvox phone systems. SIP registration failures, one-way audio, choppy calls.
• Security incidents like compromised accounts and session token theft. EDR, email security, vulnerability scanning and HIPAA risk assessments.
• Hyper-V hosts and failover clusters, physical-to-virtual migrations, backups and restore testing. Basic SQL Server work for the databases behind EHR systems.

What you bring:

• 7 years of hands-on IT experience, with at least 2 in a senior, lead, or mentoring role
• Strong on-prem Active Directory and Microsoft 365 skills
• Real experience with firewalls, IPsec VPNs, and VoIP troubleshooting
• Hands-on Hyper-V experience, including clustering
• You already use AI tools to troubleshoot, script, and document faster
• The ability to explain a problem to a physician or office manager who isn't technical
• A valid driver's license and reliable transportation

Healthcare IT experience is strongly preferred. That means EHR and practice management systems, HL7 interfaces, or clinical devices. MSP and Linux experience help too.

This is a fully on-site role at our Cape Coral office, with travel to client sites. There's no remote or hybrid option. You'll be part of the after-hours on-call rotation, and migrations sometimes mean evening or weekend work.

Salary starts at $90,000, based on experience. Benefits include paid time off, a matching 401(k), health insurance reimbursement, and support for professional development and certifications.