Senior IT Support Specialist

This is a fully remote position, open to applicants in Costa Rica.

📋 Description

• Act as the escalation point for intricate or high-priority incidents and requests from the IT support team.

• Diagnose and resolve issues across Microsoft 365, Windows, macOS, Azure Virtual Desktop, user access, and remote connectivity.

• Lead the response to major incidents and keep affected users and stakeholders informed.

• Oversee endpoint lifecycle activities, including the provisioning, configuration, shipping, and maintenance of laptops, mobile devices, and peripherals.

• Conduct onboarding and offboarding processes, which encompass account setup, access, and equipment management.

• Administer Microsoft 365, Active Directory, and Entra ID, including user accounts, groups, licensing, MFA, and access requests.

• Support Microsoft Intune operations, which involve app deployment, patching, and endpoint policies, in collaboration with the Infrastructure team.

• Develop and maintain knowledge base articles, runbooks, and how-to guides; provide training to the IT support team to enhance first-contact resolution.

• Manage incidents, requests, and problems; monitor ticket trends and assist in meeting SLAs.

• Identify recurring issues, conduct root cause analysis, and propose permanent solutions.

• Discover opportunities to automate routine tasks and broaden self-service options, including AI-driven tools.

• Assist the Security team with access reviews, device compliance, phishing reports, and data protection practices.

⛳️ Requirements

• Over 5 years of experience in IT support, with a proven ability to handle escalated and complex issues.

• Strong proficiency in Microsoft 365, Windows, and macOS.

• Familiarity with Active Directory and Entra ID, including user management, hybrid identity, and MFA.

• Practical experience with Microsoft Intune, including app deployment, patching, and endpoint policies.

• Experience in supporting virtual desktop environments.

• Knowledge of ITSM platforms such as Freshservice, ServiceNow, or similar tools.

• Excellent written and verbal communication skills in English.

• Strong troubleshooting, prioritization, and time management abilities.

• Proven history of creating clear, current, and user-friendly documentation for non-technical audiences.

• Comfortable working asynchronously in a distributed, remote-first setting.

• Practical experience using AI tools to automate or expedite support tasks.

• Experience in a law firm or other professional services setting is a plus.

• Familiarity with Nerdio or other AVD management tools is an advantage.

• PowerShell scripting skills are a bonus.

• Experience in website hosting and administration, including DNS and domain management, SSL/TLS certificates, CMS administration, cloud or managed hosting, and CDN/WAF services like Cloudflare, is a plus.

🏝️ Benefits

• 100% remote work.

• Full-time independent contractor arrangement.

• Opportunity to work in a distributed, remote-first environment.

• Diverse and inclusive workplace.

• Chance to collaborate with world-class talent and have unique perspectives valued.