System Administrator - Infrastructure & Information Security

Readdle is a pioneering force in the personal productivity space on Apple devices, having shaped the landscape since 2007. Our mission is to empower individuals and teams with innovative technology, enhancing their efficiency and creativity. We are dedicated to crafting exceptional mobile and desktop experiences for those who aspire to achieve more.

The Difference You Will Make

As a System Administrator, you'll own access, support, and asset management for our distributed team. You'll also contribute to the team's infrastructure projects, from security improvements to internal systems consolidation. Another focus is automating recurring requests, so there's room in your day for infrastructure work.

Tech Stack:

• Google Workspace, Atlassian ecosystem: Jira, Jira Service Management, and Confluence
• GitHub, Jenkins
• macOS fleet with MDM (Apple devices for nearly the whole team)
• AWS, GCP, Linux

What you'll work on:

• Own the full access lifecycle (provisioning, reviews, and revocation) with every step documented in-ticket.
• Resolve support and service requests end-to-end so people across the distributed team can keep working without friction.
• Administer Google Workspace and Jira Service Desk, including the intake forms and workflows that shape how requests arrive.
• Administer our GitHub organization: members, teams, repository permissions, and access as part of the standard access lifecycle.
• Maintain Jenkins nodes and the GitHub-Jenkins integration (webhooks, credentials, build agents) that engineering teams rely on every day.
• Manage a fleet that is almost entirely Apple: enrollment, configuration profiles, OS updates, and security baselines through MDM.
• Identify recurring request types and remove them through automation and self-service.

This role will give you the opportunity to:

• Own access and asset management end-to-end.
• Work hands-on with AI tooling in IT operations, from triage and request classification to reducing manual handling.
• Reduce your own manual load through automation, with the freedom to propose and build it.
• Be part of shaping how IT works here and grow with it as it matures toward enterprise-level processes.

About You:

• 3+ years of experience in system administration, including hands-on Google Workspace and macOS administration in a company environment.
• Proven experience owning asset management.
• Intermediate Linux command-line skills and a working knowledge of AWS and GCP.
• Discipline in documentation and in following access policy.
• A service-oriented approach: you work comfortably with non-technical users and take each request through to a working outcome.
• Good written and verbal English (B2 preferred).

It's a plus if you have:

• Experience configuring Jira/Jira Service Management.
• Hands-on MDM administration experience.
• Scripting skills for task automation and an understanding of CI/CD.
• Linux or networking certifications.

What you will get at Readdle:

• Customer-centric culture. We put our users at the heart of everything we do. Every team member has the opportunity to engage directly with customers, gaining insights that shape meaningful, delightful experiences for millions worldwide.
• Relentless growth. We’re committed to mastery in our craft. We take ownership of our work, decisions, and outcomes, and we see feedback as a catalyst for growth. Every challenge is an opportunity to learn, evolve, and raise the bar.
• Exceptional people, exceptional team. Our greatest strength is our people. We care deeply about each other, work transparently, and celebrate collective success. Together, we build an environment where everyone can do their best work and grow beyond their potential.
• Real impact. We design products that truly matter. Our focus is on delivering tangible value, simplifying complexity, pushing boundaries, and continuously improving how we build and deliver solutions to our users.
• Culture of innovation.  We embrace curiosity and creativity in everything we do. Fresh ideas are not just welcomed, they’re expected, celebrated, and turned into real innovations that shape the future of our products and company.