IT Support Specialist

About this role

APPLICATIONS FROM OUTSIDE COLOMBIA AND BRAZIL WILL NOT BE CONSIDERED FOR THIS ROLE Robots & Pencils is an applied AI engineering firm building the next frontier of business architecture. We design and ship AI co-workers that integrate into enterprise operations and deliver measurable results for our clients. We’re all in on AWS, combining deep UX capability with senior engineering talent to get AI into production fast and keep it there.

We’ve earned the trust of leaders across Consumer Products and Retail, Education, Energy, Financial Services, Healthcare, and Manufacturing and more, and earned a reputation as the nimble alternative to traditional global systems integrators. Founded in 2009, with delivery centers in Canada, the United States, Eastern Europe, and Latin America, we are smaller, faster, and more senior by design. Our teams average 15+ years of experience.

We move fast, sweat the details, and build things that actually ship. Position Overview We’re looking for an IT Support Specialist based in Latin America to join our IT team as a full-time contractor. This is a plug-and-play role for someone who already knows the tools, owns their tickets, and doesn’t need handholding to get things done. You’ll be the first line of escalated support for R&P employees across North America and Latin America — handling the issues that go beyond basic triage, keeping our core platforms running smoothly, and making sure people get back to work fast.

You’ll work directly with our Senior Systems Administrator and operate with a high degree of autonomy in a remote-first, globally distributed environment. Why This Role Matters 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 <li data-leveltext="•" data-font="Arial" data-listid=