🌍 Why this role matters
At Gypsy, leadership isn’t just about big ideas — it’s about the clarity, coordination, and focus that bring them to life. As a Business Assistant to our CEO, you’ll play a vital role behind the scenes, ensuring operations run smoothly, priorities stay aligned, and the leadership team stays supported.
You’ll be the trusted right hand helping drive momentum — managing tasks, coordinating across teams, and ensuring nothing gets missed. You’re proactive, detail-obsessed, and thrive in fast-paced environments where things move quickly and purposefully.
🧭 What makes you a great match- 3+ years supporting C-level executives in an operational, assistant, or project-focused role.
- You’re obsessively organized, deeply reliable, and unshakably calm under pressure.
- Exceptional written and verbal communication skills — you know what to say and when.
- Proactive mindset — you don’t wait to be asked; you get it done.
- Familiar with Slack, Asana, Trello, Notion, and G Suite tools.
- Comfortable working in high-speed environments with shifting priorities.
Requirements
📋 Your daily adventures:
Execution Support for the CEO
- Maintain a structured and up-to-date system of all CEO initiatives, tasks, decisions, and commitments (business and personal).
- Track progress and deadlines proactively, ensuring delivery without requiring additional involvement from the CEO.
- Escalate delays, blockers, and risks in a timely manner with clear proposals for next actions.
Oversight of Priorities Across Stakeholders
- Maintain a consolidated and accurate view of the top priorities and critical deliverables of key team members and departments.
- Monitor progress on commitments made to the CEO and ensure that information reflects reality rather than intentions.
- Provide regular, concise status updates so the CEO always has a clear situational picture without requesting it.
Personal Logistics and Travel Management
- Handle travel arrangements end-to-end (flights, accommodations, transportation, itineraries).
- Coordinate logistics for events, offsites, and engagements.
- Ensure frictionless execution of travel and personal scheduling with minimal CEO involvement.
Information Structure and Documentation
- Organize documents, notes, contracts, and relevant records for fast access and zero loss of information.
- Prepare materials and background information in advance of meetings and interactions when required.
- Ensure that both personal and work-related information are consistently systematized.
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.
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