IT Support Specialist

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  

• 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  

Required Experience & Skills  

• 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 

Helpful Extras and Unique Skills  

• 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 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. 

• Direct in a way that makes the work better.  You give honest feedback. You’d rather have the hard conversation than blow smoke. 

• 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. 

• Built for ownership.  You honor commitments, admit mistakes fast, and back your teammates when a decision costs something. No handoffs, no finger-pointing. 

• All in.  You treat clients’ businesses like your own. You take the work seriously without taking yourself seriously. 

• Resourceful when the budget, timeline, or team is tight.  Constraints don’t slow you down. They sharpen you. 

• 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.