Senior Technical Engineer – Healthcare MSP

We're a managed service provider exclusively focused on healthcare IT, supporting complex private practice environments where technology directly impacts patient care. Our team is small, senior-heavy, and deeply specialized.

The Role

You'll own complex healthcare IT environments end-to-end, serving as the primary technical resource for a portfolio of medical practices. This covers everything from network architecture to HIPAA compliance support to EHR troubleshooting.

This is an in-office position in Cape Coral, FL. We deliver 100% of our support remotely using professional-grade RMM, documentation, and communication tools. Occasional travel to client sites may be required.

You'll also mentor junior staff, refine our standards, and help shape how we deliver services.

What You'll Do

•      Architect, implement, and maintain Windows server/desktop environments, network infrastructure, and security controls

•      Administer Microsoft 365 and Azure environments with a focus on security and compliance

•      Design and manage firewall rules, VPN configurations, VLANs, and network segmentation

•      Develop and test backup and disaster recovery strategies

•      Support EHR/EMR systems and coordinate with healthcare software vendors

•      Assist clients with HIPAA Security Rule compliance: risk assessments, policy implementation, audit preparation

•      Communicate clearly with non-technical stakeholders about risks, options, and recommendations

•      Manage vendor relationships and hold partners accountable to SLAs

Required

•      5 years in a hands-on technical support or systems engineering role

•      Strong Windows Server and desktop administration skills

•      Solid networking fundamentals: TCP/IP, DNS, DHCP, VLANs, firewalls, VPN

•      Experience with Microsoft 365 and Azure administration

•      Hyper-V virtualization administration

•      VoIP system administration and troubleshooting

•      Ability to manage multiple client environments simultaneously

•      Excellent written and verbal communication skills

Strongly Preferred

•      Prior MSP experience

•      Healthcare IT background: EHR/EMR support, HIPAA compliance, healthcare vendor ecosystems

•      Experience with RMM and PSA platforms

•      Backup and disaster recovery planning and execution

Nice to Have

•      Linux/Unix administration and scripting

•      VMware experience

•      Industry certifications: CISSP, CISM, Microsoft Azure, Cisco, CompTIA Security

Benefits

•      Salary: $70,000 to $90,000 depending on experience and qualifications

•      Performance bonuses tied to client satisfaction and project delivery

•      401(k) with employer match

•      Health insurance stipend via QSEHRA

•      Certification training and exam reimbursement

•      10 days PTO first year, 15 days starting year two, plus paid holidays

How to Apply

Send your resume, a brief note about your healthcare IT experience, and a 90-second video introduction to jobs@ocsit.com.

In your video, tell us why you're a good fit and answer one of these questions:

•      Describe a time you explained a technical problem to a non-technical client.

•      How do you prioritize when multiple clients have urgent issues?

•      What's your approach when you inherit a poorly documented environment?

•      Tell us about a time you had to deliver bad news to a client.

Applications without a video will not be considered.

No recruiters, please.