We are looking for a proactive and reliable System Administrator who will help maintain and improve our internal infrastructure, support employees across the company, and ensure smooth day-to-day IT operations. You will play a key role in managing access, devices, internal systems, and supporting operational security processes while working closely with the SysAdmin team.
Requirements🧭 What Makes You a Great MatchMust-have
- 4+ years of experience in System Administration or IT Operations;
- Strong hands-on experience with macOS administration;
- Proven experience managing Apple device fleets;
- Solid understanding of Linux administration basics;
- Experience administering Google Workspace environments;
- Good understanding of networking fundamentals (DNS, VPN, TCP/IP);
- Experience with Identity & Access Management processes;
- Familiarity with internal support and ticketing systems;
- Strong documentation and process discipline;
- English level: Upper-Intermediate or higher.
- Experience with proxy or networking tools;
- Experience working with infrastructure providers such as Hetzner or DigitalOcean;
- Basic scripting or automation skills.
- Support daily administration of internal IT infrastructure and corporate tools;
- Manage user access provisioning and deprovisioning processes;
- Coordinate employee onboarding and offboarding;
- Assist internal users with infrastructure, access, and device-related issues.
- Coordinate daily workload across SysAdmin support levels (L1 & L2);
- Monitor support queues and ensure effective ticket distribution;
- Maintain SLA compliance across support operations;
- Act as an escalation point for complex technical issues.
- Administer and support Google Workspace services;
- Manage VPN and network access configurations;
- Support endpoint and device administration processes;
- Maintain and troubleshoot internal systems and tooling.
- Enforce access policies and permission management standards;
- Support 2FA enforcement and security-related controls;
- Review audit logs and monitor access-related changes when required.
- Maintain hardware and software asset inventory;
- Keep infrastructure documentation and operational procedures up to date;
- Ensure all operational knowledge is properly documented and maintained.
Benefits
💸 Flexible payment options: choose the method that works best for you;
🎁 Financial perks: Bonuses for holidays, B-day, work milestones and more - just to show we care;
📈 Learn & grow: We cover courses and certifications — and offer real opportunities to grow your career with us;
🥐 Benefit Сafeteria: Choose what suits you — sports, language courses, therapy sessions, and more;
🎉 Stay connected: From team-building events to industry conferences — we bring people together online, offline, and on stage;
💻 Modern Equipment: We provide new laptops along with essential peripherals like monitors and headphones for a comfortable workflow;
🕘 Your schedule, your rules: Start your day at 9, 10, or even 11 — we care about results, not clock-ins.
If this role sounds like a good fit for you, we’d love to hear from you — apply and tell us a bit about yourself.
Skills Required
- 4+ years of experience in System Administration or IT Operations
- Strong hands-on experience with macOS administration
- Proven experience managing Apple device fleets
- Solid understanding of Linux administration basics
- Experience administering Google Workspace environments
- Good understanding of networking fundamentals
- Experience with Identity & Access Management processes
- Familiarity with internal support and ticketing systems
- Strong documentation and process discipline
- English level: Upper-Intermediate or higher
What We Do
We’re Gypsy — a digital entertainment collective that transforms work into an expedition. For five years, we’ve been charting new territories and creating our path instead of following others. We are a team of 100+ free-spirited professionals thriving in a remote-first environment, where you can work from anywhere and turn every project into an adventure. At Gypsy, we strip away the corporate fluff to create a place where you can truly make your mark. Our culture is about how we put our principles into action every day. We're human-powered – placing people at the heart of everything we do, because that's how we thrive together. We believe in clear connections – speaking honestly, sharing openly, and building trust that fuels real progress. We stay in growth motion – taking risks, adapting quickly, and turning challenges into stepping stones. And we're always exploring – pushing boundaries with genuine curiosity to discover what's next. This isn't just who we want to be — it's who we are. Modern wanderers connect cultures through play, make important decisions, and celebrate our shared journey along the way. Team up and roam with us.
