Posted Sep 11, 2026

Senior IT & Security Engineer (AI-Native)

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🚀 We Don't Have an Office. We Still Have IT.

Most companies scale IT by hiring more admins to answer more tickets. We'd rather hire one engineer who automates the tickets out of existence.

WorkFlex is a remote-only company. Our "office" is ~140 laptops (half Windows, half Mac) spread across beaches, mountains, and home offices around the world. Your mission: build the identity, device, and security platform for a company that holds ISO 27001 and is heading toward C5 / SOC 2 Type 2.

The starting position is rare: no legacy Active Directory, no on-prem servers, no office network. A greenfield with a clear mandate to build.

🌍 The Lifestyle: 183 Days of Workations

We are a remote-only company. You can work from a beach, a mountain, or your home office. We offer 183 days of workations per year because we believe the best solutions come from people who are inspired by their surroundings. Your platform has to survive hotel Wi-Fi and captive portals. You'll be building for exactly the life you're living. Note: for data protection and security reasons, we hire EU-based only for this role.

🛠️ The Workflow: AI-Native IT

At WorkFlex, we operate differently. If your happy place is clicking through admin portals all day, you are the wrong profile.

🎯 What You Will Do

⭐ What You Need to Succeed

➕ Bonus Points

📈 What Success Looks Like After Year One

🚀 Why join us at WorkFlex

We may use AI-assisted tools to support parts of our recruitment process. These tools help our team review applications more efficiently, and all hiring decisions are made by humans.

4+ years managing modern Microsoft-stack IT (Entra ID/M365/Intune), device lifecycle and identity, scripting (PowerShell/Python/TypeScript), EDR and email hardening, AI-tool proficiency, EU-based and English C1+.

Key Responsibilities

Skills & Tools

Microsoft Graph API, Claude, Claude Team, Gemini, n8n, WireGuard, NetBird, Tailscale, PowerShell, Python, TypeScript, Entra ID, Intune, Autopilot, Apple Business Manager, Jamf, Kandji, Mosyle, Personio

Job Details

About WorkFlex

A remote-first HR tech startup providing an automated platform for international travel and remote-work compliance. — Industry: Information Technology