📋 Your daily adventures
System Administration
- Support, configure, and maintain operating systems: macOS, Windows, Linux;
- Administer workstations, peripherals, and VPN infrastructure;
- Take full ownership of user and corporate equipment (inventory and stock);
- Proactively handle non-standard situations and incidents within the scope of system administration;
Security & Access Management
- Manage access controls, enforce 2FA, and maintain security policies;
- Grant and revoke permissions, conduct audits, and respond to security incidents;
CMDB & Digital Assets
- Maintain CMDB and documentation, ensuring data accuracy;
Process Improvement & Collaboration
- Optimize onboarding and offboarding processes;
- Contribute to the development and maintenance of internal guides, policies, and documentation;
- Collaborate closely with TechOps, HR, and Finance teams.
Requirements
🧭 What makes you a great match
- 4+ years of experience as a System Administrator or IT Support Specialist;
- Strong analytical mindset and ability to solve problems quickly in a fast-paced environment;
- Proactive, organized, and accountable approach to work;
- Keen attention to critical details in daily operations;
- Solid knowledge of macOS, Windows, Linux, networking protocols, and VPN;
- Understanding of IT infrastructure in companies of 100–200 employees;
- Hands-on experience with HelpDesk (Asana), ITIL/CMDB, OKTA, and asset management systems;
- English level: Upper-Intermediate or higher (communication in tools, with vendors, and documentation).
Benefits
💸 Flexible payment options: choose the method that works best for you.
🧾 Tax assistance included: we handle part of your taxes and provide guidance on the local setup.
🎁 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.
Top Skills
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.
