System Administrator

💫About the Role💫
We are looking for a mid-level IT Support Specialist/System Administrator reporting directly to the company's CTO.
Your primary responsibility will be to provide day-to-day IT support while maintaining a consistently high level of service throughout the rollout of these automations. You will follow the CTO's guidance as support processes evolve and ensure a smooth transition without disrupting client operations.

💫Working Hours
This is a standard part-time position with a required daily overlap with the client's business hours (U.S. Eastern Time).

💫Responsibilities
Handle day-to-day support requests while meeting a 2-hour SLA during business hours.
Administer the cloud-based RMM platform, including device monitoring, inventory management, and remote access.
Maintain the client's security stack, including:Antivirus/EDR
Multi-Factor Authentication (MFA)
Email spam filtering
DNS filtering
Security awareness/phishing training
Backup administration, including monthly restore testing

Perform employee onboarding and offboarding, including device preparation and account provisioning according to established procedures.
Maintain accurate and up-to-date IT documentation.
Prepare monthly client reports.
Use AI-powered support tools (chatbot, automated ticket triage, automated reporting) introduced by the CTO, provide feedback during testing, and assist with their adoption into daily operations.
Ensure uninterrupted support quality while new automation processes are introduced, following guidance from the CTO.
Coordinate occasional on-site work with a local contractor via phone or video calls. Historically, this occurs approximately 2–3 times per year.

Typical workload: Approximately 14 support tickets per month based on one year of historical data. Ticket volume is uneven, ranging from quiet weeks to occasional peak weeks with 20+ requests.

💫Requirements
Experience as an IT Support Specialist or Systems Administrator supporting small or medium-sized businesses.
Familiarity with RMM/PSA platforms such as Atera, Syncro, NinjaOne, ConnectWise, Datto RMM, or similar (expert-level knowledge is not required).
Experience administering Microsoft 365 and Microsoft Entra ID, including MFA, Conditional Access, and basic security configuration.
Working knowledge of network infrastructure (firewalls, switches) sufficient to maintain existing environments without requiring hardware replacement expertise.
Basic understanding of cybersecurity best practices for SMB environments, including EDR, backups, phishing protection, and endpoint security.
Confident use of AI tools in daily work as an end user (developer experience is not required).
English proficiency sufficient for direct communication with U.S.-based clients and end users.
Availability for real-time collaboration during the initial migration period.

Nice to Have
Previous experience working for an MSP (Managed Service Provider) or outsourced IT support organization.
Experience participating in client migrations between IT service providers.
Basic familiarity with scripting or API-based automation, which will help when collaborating with the CTO on AI-driven workflow improvements.