Senior IT Systems Administrator (Site lead)

ABOUT ZIP Zip is the AI platform for enterprise procurement — built for humans and agents working together. By orchestrating procurement across teams, tools, and suppliers with the help of AI agents, companies can secure the resources they need to innovate faster than ever before. The world’s most influential enterprises trust Zip, including T-Mobile, OpenAI, AMD, Mars, Dollar Tree, and more. Together they’ve saved over $8 billion and processed over $500 billion in spend. Zip’s team includes product leaders from Apple, Airbnb, and Meta, as well as former procurement leaders from United Health, Sanofi, MGM Resorts, Discover, and NASA. Backed by Adams Street, Alkeon, BOND, CRV, DST, Tiger Global, and Y Combinator, Zip has raised $371 million, most recently at a $2.2 billion valuation and has been recognized by Forbes Fintech 50, Fast Company's Most Innovative Companies, Inc. Best in Business, and LinkedIn Top Startups. YOUR ROLE Zip is looking for an experienced systems administrator who can bridge the gap between high-level system engineering and essential onsite operations. In this role, you aren’t just managing systems - you are the Onsite IT Lead, serving as the technical face of our office while ruthlessly eliminating manual tasks through advanced scripting and intelligent orchestration. You will join a high-impact IT organization to build a "Code-First" infrastructure that scales. Your goal is to make people happy by creating simple, automated, and repeatable solutions for everyone. At Zip, we aren't just looking for an admin; we’re looking for a builder. If you want to play a pivotal role in scaling our infrastructure through code, security, and cutting-edge technology while leading our onsite experience, we want to hear from you. Please note: this role will be onsite in our Toronto office 5 days per week. YOU WILL - Automated Lifecycle & Identity: Architect end-to-end automation for employee onboarding/offboarding (Okta, Google Workspace, Slack). Your goal is "Zero-Touch" provisioning and a secure, instant-revoke "kill switch" for departures. - Onsite IT Leadership: Serve as the primary technical lead for the physical office. You will own the health of our conference rooms, A/V integrations, and office tech, ensuring the workspace remains a frictionless environment for onsite and hybrid teams. - Workplace & Cross-Team Collaboration: Partner closely with Workplace and People teams to manage office expansions, desk deployments, and A/V upgrades. You will act as the IT site lead for physical workspace improvements. - Infrastructure & Network Security: Manage and secure the corporate network (WiFi, LAN, VPN, Firewalls) and endpoints (Iru/Intune). Collaborate with Information Security to automate compliance monitoring and threat remediation. - Advanced Scripting & Tooling: Build custom scripts (Python, PowerShell, or Bash) and utilize APIs to integrate our SaaS stack, transforming manual "Help Desk" tasks into automated workflows. - Proactive Documentation: Take the initiative to write and maintain high-quality runbooks and internal SOPs. You believe that if a process isn't documented and repeatable, it isn't finished. - High-Touch Support: Provide top-tier support for Mac/Windows hardware and software via Jira Service Management, using these interactions to identify the next big automation project. QUALIFICATIONS - Experience: 5+ years in IT Systems Administrator; previous experience as an Onsite Lead is a plus. - Networking: Strong understanding of TCP/IP, VLANs, DNS, DHCP, and firewall management. - Security: Experience with MDM (Iru/Intune) and EDR tools (CrowdStrike). - Identity & SaaS: Advanced mastery of Okta (Lifecycle Mgmt) and Google Workspace. - Automation: Experience with automation workflow software, REST APIs and proficiency in Python, Bash or PowerShell for script deployment. - Onsite Tech: Hands-on experience with Zoom Rooms, A/V hardware, and office networking. BONUS POINTS - AI Implementation: Leveraging LLM