Senior Technical Engineer – Healthcare MSP

Senior Technical Engineer – Healthcare MSP

ENT IT Solutions & Cybersecurity Leader | Award-Winning MSP | Best-Selling Author | Speaker on Cybersecurity, Tech, AI, & HIPAA | Serial Entrepreneur

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.

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.

• 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

• 5+ years in a hands‑on technical support or systems engineering role
• Strong Windows Server and desktop administration skills
• Experience with Microsoft 365 and Azure administration
• VoIP system administration and troubleshooting
• Ability to manage multiple client environments simultaneously
• Excellent written and verbal communication skills

• Experience with RMM and PSA platforms
• Backup and disaster recovery planning and execution

• Linux/Unix administration and scripting

• 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

• Send your resume, a brief note about your healthcare IT experience, and a 90-second video introduction to
• 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.