Gypsy Collective

Senior System Administrator

Gypsy Collective  β€’  Ukraine (Remote)  β€’  4 days ago
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Job Description

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 Match

Must-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.

Nice-to-have

  • Experience with proxy or networking tools;
  • Experience working with infrastructure providers such as Hetzner or DigitalOcean;
  • Basic scripting or automation skills.

πŸ“‹ Your Daily Adventures

IT Operations

  • 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.

SysAdmin Team Coordination

  • 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.

Infrastructure Support

  • 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.

Security & Access Control

  • Enforce access policies and permission management standards;
  • Support 2FA enforcement and security-related controls;
  • Review audit logs and monitor access-related changes when required.

Documentation & Asset Management

  • 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

πŸ’Έ 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;
πŸ“ˆ Learn & grow: We cover courses and certifications β€” and offer real opportunities to grow your career with us;
πŸ₯ Benefit Π‘afeteria: Choose what suits you β€” sports, language courses, therapy sessions, and more;
πŸŽ‰ Stay connected: From team-building events to industry conferences β€” we bring people together online, offline, and on stage;
πŸ’» Modern Equipment: We provide new laptops along with essential peripherals like monitors and headphones for a comfortable workflow;
πŸ•˜ Your schedule, your rules: Start your day at 9, 10, or even 11 β€” we care about results, not clock-ins.

If this role sounds like a good fit for you, we’d love to hear from you β€” apply and tell us a bit about yourself.

Gypsy Collective

About Gypsy Collective

We’re Gypsy β€” 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 β€” 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.

Industry
Marketing & Advertising
Company Size
11-50 employees
Headquarters
Unknown
Year Founded
2020
Website
gypsy.co
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