IT Support & Systems Specialist (Entry-Level)

JOB TITLE: IT Support & Systems Specialist (Entry-Level)

LOCATION: Ossining, NY

TYPE: Full-Time

ROLE OVERVIEW We are looking for a proactive, highly organized IT Support Specialist to help support our technical ecosystem. This is a unique entry-level role that blends traditional desktop support with junior systems administration.

Our environment is 100% cloud-forward and hardware-diverse. We operate a 50/50 mix of Windows and macOS. We utilize Google Workspace for our primary identity and 99% of our email (Gmail), alongside Box, Office 365, and Slack. You will also assist in supporting our server infrastructure hosted on Proxmox.

A NOTE ON WORKFLOW We do not use a traditional ticketing system. You will be responsible for managing requests via Slack and email, using Notion as our central nervous system for project tracking, asset management, and documentation.

KEY RESPONSIBILITIES

• Primary Desktop Support: Troubleshoot hardware, software, and connectivity issues for both MacBook and Windows laptop users.
• Infrastructure Management: Assist in monitoring and maintaining our Proxmox VM environment, ensuring virtual machines are healthy and performing routine resource checks.
• Data Protection & Recovery: Manage and monitor Acronis Backup. You will ensure local and cloud backups are successful and perform periodic restore tests to ensure data durability.
• Security Operations: Administer Bitdefender across all endpoints, responding to alerts and ensuring agent compliance on all company devices.
• SaaS Administration: Handle user onboarding/offboarding in Google Workspace and manage permissions within Box and Office 365 (including specialized support for a limited number of Outlook desktop users).
• Knowledge Architecture: Help build and maintain the IT Wiki in Notion. Document recurring fixes, maintain hardware inventory, and create self-service guides for staff.
• Triage & Communication: Monitor Slack/Email for help requests, providing clear updates and self-organizing your tasks in Notion.

TECHNICAL REQUIREMENTS

• OS Mastery: Proficient in troubleshooting both Windows 10/11 and macOS (Sonoma/Sequoia).
• Virtualization Basics: Familiarity with Proxmox, VMware, or VirtualBox. You should understand what a VM is and how to perform basic tasks like start/stop/restart.
• Google Workspace: Knowledge of Google Admin console and Gmail troubleshooting.
• Security & Backup: Understanding of Bitdefender (or similar EDR) and Acronis (or similar backup solutions).
• Notion Proficiency: Ability to build and maintain databases and documentation templates.

ABOUT YOU

• The "Homelab" Enthusiast: You are likely the person who runs a media server or a private cloud at home. You are curious about how servers work, not just desktops.
• The Organizer: You thrive in environments where you manage your own "ticket" queue. You are a natural documentarian who believes that if it isn't in Notion, it didn't happen.
• The Translator: You can explain technical risks and solutions to non-technical staff with patience and empathy.

Pay: $50,000.00 - $60,000.00 per year

Benefits:

• 401(k)
• Dental insurance
• Health insurance
• Life insurance
• Paid time off
• Vision insurance

Work Location: In person