Jobs at Charles IT

Provide field and escalation support for clients, troubleshoot end-user and Microsoft technology issues, administer Windows, Office 365, SQL, SharePoint, VMware, and Hyper-V environments, and support backup, disaster recovery, networking, and security devices. Communicate ticket progress and service changes, document procedures and service work in ConnectWise, manage multiple priorities, and work independently in a client-focused environment.

Participate in a 12-week in-house IT trainee program covering help desk support, Active Directory, Microsoft 365 administration, desktop and printer setup, basic server maintenance, network audits, first-level security incident response, ticket management, and client communication. Trainees also assist with office tasks, equipment deliveries, technical projects, training modules, and certifications, with potential advancement to Desktop Support Specialist.

Serves as the primary client liaison for technical escalations and business objectives. Builds client relationships, assesses needs, develops best-practice roadmaps, mentors technical teams, validates proposed solutions, coordinates project delivery, communicates initiative progress, and maintains documentation. Requires four or more years of IT experience, strong communication and organizational skills, and a valid U.S. driver's license.

Leads and develops the vCIO team, establishing standards for QBRs, technology roadmaps, budgeting, and client communications. Ensures consistent strategic advisory delivery, alignment between service and strategy, and proactive lifecycle planning. Monitors client health, retention, growth, and at-risk accounts while coaching recovery strategies. Maintains CRM and PSA data quality in ConnectWise Manage, improves advisory processes, identifies training needs, and reports performance and client experience metrics to leadership.

Provides first-level escalated IT support by diagnosing hardware, software, operating system, network, account, and peripheral issues. Sets up and decommissions user accounts and computers, installs and troubleshoots software, supports Windows, Linux, and macOS environments, and assists with networking, vendors, and repairs. Documents work accurately, communicates technical issues clearly to users, manages multiple tasks, and maintains strong client relationships.

Lead month-end, quarter, and year-end close; review journals and reconciliations; prepare financial statements and variance analysis; manage audits; oversee balance sheet and working capital; improve accounting processes; and coach an accounting team while partnering cross-functionally on accounting matters.

Lead and execute technical IT projects from kickoff through post-go-live support. Perform hands-on engineering for hypervisor, email, server, network, and office build-out migrations. Coordinate with clients, vendors, and internal teams, maintain documentation, provide status updates, record time in ConnectWise, and participate in continuous improvement and post-implementation stabilization.

Part-time administrative intern supporting office operations: run errands and interoffice mail, restock supplies, assist events, manage vehicle scheduling, learn ticketing system, and provide ad-hoc project support.