Robots and Pencils - IT Support Specialist
Requirements
• 2 years of hands-on IT support experience, with at least 1 year at an L2 or escalation level • Strong working knowledge of Microsoft 365 administration — Entra ID, Exchange Online, SharePoint, Teams, and OneDrive • Experience supporting both macOS and Windows endpoints in a remote or hybrid environment • Familiarity with MDM platforms (Rippling, JumpCloud, Jamf, Intune, or similar) for device management and enrollment • Basic understanding of SSO and MFA concepts — able to troubleshoot user-facing login issues • Experience managing tickets and workflows in Jira Service Management, Zendesk, or a comparable ITSM platform • Strong written and spoken English — clear, professional, and direct in all communications; strong written and verbal Spanish • Ability to work independently, manage your own queue, and know when to escalate • Exposure to endpoint security tools such as Sophos, CrowdStrike, or similar XDR platforms • Experience in a startup, agency, or distributed tech company environment • CompTIA A+, Network+, Microsoft MS-900, or similar certifications • You’ll Do Well Here if You Are • A doer. You see something broken and fix it. You’d rather move on clarity than wait for certainty. • A doer. • A fast learner who knows you don’t know everything. The AI landscape changes weekly. You’re senior enough to know better and curious enough to keep learning anyway. • A fast learner who knows you don’t know everything. • Direct in a way that makes the work better. You give honest feedback. You’d rather have the hard conversation than blow smoke. • Direct in a way that makes the work better. • Obsessed with craft. You know genius is in the details. You ship exceptional, not perfect, and you don’t put your name on work you wouldn’t stand behind. • Obsessed with craft. • Built for ownership. You honor commitments, admit mistakes fast, and back your teammates when a decision costs something. No handoffs, no finger-pointing. • Built for ownership. • All in. You treat clients’ businesses like your own. You take the work seriously without taking yourself seriously. • All in. • Resourceful when the budget, timeline, or team is tight. Constraints don’t slow you down. They sharpen you. • Resourceful when the budget, timeline, or team is tight. • Glad to be in the room with people who care as much as you do. Our teams average fifteen-plus years of experience. We hire people who push each other to do better work. • Glad to be in the room with people who care as much as you do.
Responsibilities
• End-User Support & Ticket Management • Handle IT support requests submitted via Slack, covering both routine issues and complex problems that require deeper technical investigation or elevated access • Resolve hardware, software, connectivity, and account-related issues for remote employees across macOS and Windows environments • Triage, prioritize, and manage your own ticket queue with minimal supervision, meeting defined SLA targets • Escalate issues to the next support level when they fall outside L2 scope, providing full context and steps already taken • Document resolutions clearly and contribute to the internal IT knowledge base to reduce repeat tickets • Microsoft 365 & Identity Administration • Manage user accounts, groups, and licenses in Microsoft Entra ID (Azure AD) and Microsoft 365 admin center • Handle access requests, permission changes, and offboarding tasks across Exchange Online, SharePoint, OneDrive, and Teams • Troubleshoot MFA issues and assist users with account access problems • Assist with SharePoint site administration and OneDrive configuration as needed • Device & Endpoint Management • Support onboarding and offboarding workflows, including device enrollment, configuration, and deprovisioning via Rippling MDM • Troubleshoot endpoint issues across macOS and Windows, including application installation, OS updates, and performance problems • Assist with Sophos endpoint agent deployment, alert triage, and policy enforcement in coordination with the Senior Systems Administrator • SaaS Platform Support • Provide user-level support for core business platforms, including Slack, Zoom, 1Password, Jira, Confluence, Greenhouse, and Harvest • Assist users with SSO login issues, account access problems, and password-related requests • Support onboarding of new hires by provisioning accounts and licenses across the R&P platform stack • Collaboration & Communication • Communicate clearly with employees at all levels in written English — in Slack, Zoom, email, and documentation • Escalate complex issues to the Senior Systems Administrator with full context and steps already taken • Participate in async handoffs and status updates in a remote-first work culture
Benefits
• At Robots & Pencils, we design AI systems for a human world. Our name says it all. Robots and pencils means engineering paired with creativity, because every agent we ship has to work for real people in real workflows. That balance is baked into how we operate. • What You’ll Do • End-User Support & Ticket Management • Handle IT support requests submitted via Slack, covering both routine issues and complex problems that require deeper technical investigation or elevated access • Resolve hardware, software, connectivity, and account-related issues for remote employees across macOS and Windows environments • Triage, prioritize, and manage your own ticket queue with minimal supervision, meeting defined SLA targets • Escalate issues to the next support level when they fall outside L2 scope, providing full context and steps already taken • Document resolutions clearly and contribute to the internal IT knowledge base to reduce repeat tickets • Microsoft 365 & Identity Administration • Manage user accounts, groups, and licenses in Microsoft Entra ID (Azure AD) and Microsoft 365 admin center • Handle access requests, permission changes, and offboarding tasks across Exchange Online, SharePoint, OneDrive, and Teams • Troubleshoot MFA issues and assist users with account access problems • Assist with SharePoint site administration and OneDrive configuration as needed • Device & Endpoint Management • Support onboarding and offboarding workflows, including device enrollment, configuration, and deprovisioning via Rippling MDM • Troubleshoot endpoint issues across macOS and Windows, including application installation, OS updates, and performance problems • Assist with Sophos endpoint agent deployment, alert triage, and policy enforcement in coordination with the Senior Systems Administrator • SaaS Platform Support • Provide user-level support for core business platforms, including Slack, Zoom, 1Password, Jira, Confluence, Greenhouse, and Harvest • Assist users with SSO login issues, account access problems, and password-related requests • Support onboarding of new hires by provisioning accounts and licenses across the R&P platform stack • Collaboration & Communication • Communicate clearly with employees at all levels in written English — in Slack, Zoom, email, and documentation • Escalate complex issues to the Senior Systems Administrator with full context and steps already taken • Participate in async handoffs and status updates in a remote-first work culture • What You’ll Bring • What You’ll Bring
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