IT Specialist (macOS & SaaS Systems) — Independent Contractor

Remote | 1099 Contract | 5–15 hrs/month

We're looking for a detail-oriented IT Specialist to provide on-demand technical support for The Matchbox's tech stack.

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WHAT YOU'LL DO

• Manage user access & identity — provisioning/offboarding, permissions, role-based access, SSO/MFA troubleshooting
• Administer core systems: Google Workspace, Okta, Slack, and 1Password
• Configure and maintain Cloudflare Zero Trust (access policies, tunnels, device posture, network security)
• Support Google Cloud app development and SSO integrations/functions
• Provide macOS support — system settings, permissions, software conflicts, performance issues
• Create and maintain IT documentation; identify recurring issues and recommend process improvements

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WHAT WE'RE LOOKING FOR

• Strong working knowledge of macOS environments
• Hands-on experience with Google Workspace, Okta, Slack, and 1Password administration
• Expertise in Cloudflare Zero Trust
• Experience with Google Cloud app development and SSO functions
• Comfortable working independently in a fully remote, ad-hoc support model
• Responsive during U.S. business hours via Slack and email
• Prior IT support or systems administration experience

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DETAILS

• Independent Contractor (1099-NEC) — you handle your own taxes, equipment, and benefits
• $35/hour, invoiced bi-weekly
• Flexible, low-commitment hours (5–15/month) — great for someone balancing other clients
• Fully remote