Helpdesk Analyst II

Swooped; United States; Remote; USD 70,000 - 100,000; Full time

Job summary

Swooped is seeking a Helpdesk Analyst II to act as a key escalation resource on the Service Desk. This remote, full-time role handles complex incidents from intake to resolution and improves service delivery through automation and documentation.

The candidate will troubleshoot macOS, Windows, iOS, Android, and SaaS apps, support executives, and collaborate with Security, Engineering, and People teams to drive platform improvements.

Qualifications

• 5+ years in service desk, desktop, or systems support.
• 2+ years in a senior or escalation-level role.
• Expert macOS and Windows support with iOS and Android devices.
• Experience administering Google Workspace and Microsoft 365, plus Entra ID (SSO/MFA).

Responsibilities

• Take ownership of complex, high-impact incidents through resolution.
• Troubleshoot across macOS, Windows, iOS, Android, SaaS apps, networking, and collaboration tools.
• Provide high-touch support to executive and VIP users with professionalism.
• Support onboarding/offboarding and identity lifecycle with People team.
• Collaborate with Security, Engineering, and business teams to resolve issues.
• Maintain IT knowledge base with runbooks and guides.
• Maintain hardware inventory and provisioning/refresh programs.
• Evaluate new tools and contribute to platform rollouts and process redesigns.

Skills

MacOS

Windows

iOS

Android

Google Workspace

Microsoft 365

Entra ID

SSO MFA

MDM Intune

Networking basics

Executive support

Education

IT degree or equivalent

Tools

Intune

Google Admin Console

Microsoft 365 Admin Center

Job description

The organization is seeking a Helpdesk Analyst II (Remote, USA) to serve as a key technical escalation resource on the Service Desk team. This full-time role owns complex incidents from intake through resolution, addresses challenging technical issues across enterprise environments, and enhances service delivery through process improvements, tooling, automation, and documentation.

Key Responsibilities

• Take ownership of complex, high-impact, and recurring technical incidents through resolution.
• Perform advanced troubleshooting across macOS, Windows, iOS, and Android devices, as well as SaaS applications, identity and access platforms, networking, and collaboration tools.
• Provide high-touch technical support to executive and VIP users with discretion and professionalism.
• Support employee onboarding, offboarding, and identity lifecycle processes in collaboration with the People team.
• Partner with Security, Engineering, and business teams to resolve issues, drive service maturity, and prevent recurring problems.
• Own the quality and structure of the IT knowledge base by creating and maintaining runbooks, troubleshooting guides, and documentation for analysts and end users.
• Maintain accurate hardware inventory records and support provisioning, recovery, and refresh programs.
• Evaluate new tools and features, contributing to IT initiatives such as platform rollouts, device refreshes, and process redesigns across modern toolsets including Atlassian Cloud, Microsoft 365, Google Workspace, Slack, Notion, Claude, and Zoom.

Required Qualifications

• 5+ years of experience in service desk, desktop support, or systems support.
• 2+ years of experience in a senior or escalation-level support role.
• Expert-level proficiency supporting macOS and Windows operating systems, alongside iOS and Android mobile platforms.
• Deep hands-on experience administering Google Workspace and/or Microsoft 365, as well as identity platforms such as Microsoft Entra ID (including SSO, MFA, and access provisioning).
• Experience utilizing mobile device management (MDM) platforms such as Microsoft Intune.
• Solid understanding of networking fundamentals, including DNS, DHCP, VPN, and Wi-Fi, and their effect on user experience.
• Strong problem-solving abilities, sound judgment, and the capacity to prioritize issues based on business impact.
• Clear communication skills suited for technical and non-technical audiences across diverse cultures and time zones.
• Ability to work a remote schedule, participate in an off-hours on-call rotation, and travel occasionally to support events.

Preferred Qualifications

• Degree in Information Technology or a related field, or equivalent practical experience.
• Professional certifications, such as CompTIA Network+, CompTIA Security+, Microsoft 365 Certified: Administrator, Google Workspace Administrator, Apple Certified Support Professional, or ITIL 4 Foundation.

Additional Information

• Employment is subject to a background check.
• Qualified applicants with arrest or conviction records will be considered for employment in accordance with the Los Angeles County Fair Chance Ordinance for Employers and the California Fair Chance Act.
• This role may have access to sensitive information, including employee records, customer data, financials, and proprietary company information.
• Perks and benefits eligibility may vary based on location and role status.