Remote Windows Server Jobs in Orlando, FL (NOW HIRING)

About the Role
We are a growing managed IT services company. We are looking for a senior-level engineer with a strong MSP background who is ready to take on broader leadership. This is a multi-faceted role that may flex across operations team management, project management, and hands-on cybersecurity implementation depending on the candidate's strengths and our team's needs.
The ideal candidate is a proven technical leader who has lived in the MSP world - someone comfortable owning escalations, mentoring technicians, standardizing processes, and driving complex projects to completion. Familiarity with cybersecurity compliance frameworks, particularly CMMC, is a plus.
This is a remote position with no office requirement; however, the role includes periodic on-site visits to client sites as needed, typically quarterly. Must be local to Orlando, FL
Responsibilities
Operations & Service Delivery
     Serve as a senior escalation point for complex technical issues across infrastructure, cloud, and security platforms.
     Help lead day-to-day service delivery operations, supporting SLA performance, ticket triage, and time-to-resolution across client environments.
     Mentor, coach, and develop helpdesk and field technicians; contribute to hiring, onboarding, training, and performance management.
     Standardize service processes, escalation workflows, and documentation to improve consistency and quality across the team.
Project Management & Implementation
     Plan, scope, and manage project solutioning and implementation from kickoff through delivery.
     Research, evaluate, and deploy new servers, network, and security technologies.
     Lead or support implementation of the MSP technology stack - EDR/MDR, SIEM, Zero Trust, Backup/DR, etc.
Cybersecurity & Compliance
     Support cybersecurity initiatives across client environments, including endpoint security (EDR/MDR), identity and access management, MFA/SSO, and firewall/VPN configuration.
     Assist with compliance readiness and alignment of environments to required controls - CMMC, SOC 2, and similar frameworks.
     Contribute to incident response planning, documentation, and outage recovery.
Qualifications
Required
     MSP experience: Demonstrated background working within a managed services provider, including familiarity with PSA, RMM and technology stack.
     Seniority: Minimum 5+ years in IT, with senior-level depth across servers, networking, virtualization, and Microsoft 365 / Entra ID (Azure AD).
     Technical breadth: Strong hands-on skills with firewalls, networking, Windows Server, remote desktop services, access management, zero trust, endpoint security, and backup/DR platforms, etc.
     Leadership & communication: Excellent customer-service skills, sound judgment, and the ability to lead, mentor, and stay composed under pressure.
Strongly Preferred
     Operations or project management experience within an MSP or technical services environment - leading teams, managing SLAs, or owning project delivery.
     Cyber compliance familiarity - CMMC, SOC 2, etc. Not a requirement, but a meaningful advantage.
Benefits
We are committed to supporting the well-being and success of our team. Our comprehensive benefits package is designed to promote a healthy work-life balance and reward your hard work, and includes:
     Medical, Dental & Vision: Comprehensive plans covering doctor visits, prescriptions, preventive care, dental services, and vision needs.
     Paid Time Off & Vacation: A generous PTO and vacation policy so you can rest, recharge, and return revitalized.
     Sick Days: Time to recover when you need it, without worrying about your job.
     Paid Holidays: Several paid holidays throughout the year to celebrate with family and friends.