[Hiring] IT Support Specialist @Robots and Pencils

Role Description

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.

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.

Qualifications

• 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 who sees something broken and fixes it.
• A fast learner who is curious and eager to keep learning.
• Direct in a way that improves work quality.
• Obsessed with craft and details.
• Built for ownership and accountability.
• All in, treating clients’ businesses as your own.
• Resourceful and adaptable under constraints.
• Glad to collaborate with others who care.