Senior Systems Administrator | VMware & Office 365

Charles IT; Chesapeake (VA); On-site; USD 75,000 - 105,000; Full time

Benefits offered by this job

401(k) plan with employer contribution

Performance-based incentive programs

Employee discount programs

Paid time off (PTO)

Paid holidays

Paid parental leave

Work-from-home (WFH) bank

Healthcare coverage

Dental coverage

Vision coverage

Life insurance

Short- and long-term disability

Flexible Spending Accounts (FSA)

Well-being resources

Dog-friendly office

Team lunches

Corporate concierge services

Team-building events

Job summary

Charles IT in Chesapeake, VA is seeking a Systems Administrator to provide end-user support, server and network administration, and escalation handling for a diverse client base.

You will manage Windows Server, Office 365/Exchange, VMware and Hyper-V environments, configure network devices, and document processes while delivering reliable, security-focused IT services in a fast-paced, client-centric team.

Qualifications

• 5+ years of experience in systems administration or a related IT role.
• Certifications such as MCSA, VCP, CCNA are a plus.
• Experience with Windows Server, Office 365/Exchange, VMware and Hyper‑V.
• Familiarity with ConnectWise, Cisco, Meraki, Datto, and related tools.
• Strong communication, multitasking, and teamwork in a fast-paced environment.

Responsibilities

• Provide support and troubleshooting to resolve technical issues for end users.
• Support Microsoft technologies: Windows Server, Office 365/Exchange, SQL, SharePoint, etc.
• Support virtual environments including VMware and Hyper‑V.
• Assist with backup and disaster recovery solutions.
• Configure, install, and support network devices and services (WAN/LAN, routers, firewalls, security).
• Communicate ticket progress and outages to customers; document processes.
• Maintain daily documentation in ConnectWise; time and expenses logging.
• Perform other duties as assigned.

Skills

Windows Server

Office 365/Exchange

VMware

Hyper-V

Networking

ConnectWise

Cisco

Meraki

Datto

Communication skills

Self-driven

Organization & detail

5+ years experience

Tools

ConnectWise

Cisco

Meraki

Datto

VMware

Office 365

Job description

Charles IT in Chesapeake, VA is seeking a Systems Administrator to provide end-user support, server and network administration, and escalation handling for a diverse client base.

You will manage Windows Server, Office 365/Exchange, VMware and Hyper-V environments, configure network devices, and document processes while delivering reliable, security-focused IT services in a fast-paced, client-centric team.