About TeamOut TeamOut is transforming how modern teams connect and collaborate. As remote work accelerates globally, companies face new challenges in building strong culture and meaningful relationships. Through frequent, purposeful, and scalable offsites, TeamOut enables organizations to bring their people together through impactful experiences. Our clients include Netflix, Kayak, Brex, PwC, Accenture, and other leading global companies. TeamOut is backed by Y Combinator and industry-leading investors. We are building the next generation of corporate offsite planning and execution. The Role We are looking for a Trip Designer to support companies in planning their retreats and offsites worldwide. This is a client-facing, sales-driven role focused on preparing proposals, sourcing venues, closing the loop with the venue, and walking them through our various event packages. You will be responsible for designing tailored proposals, coordinating with venues and partners, and ensuring clients receive clear, accurate information that helps them choose the right retreat location. The role is remote and requires working US time zones. Compensation is commission-based, and most team members earn around $5,000/month consistently.

Key Responsibilities

• Prepare detailed travel proposals including hotels, restaurants, transportation, and activities.
• Collaborate with the Head of Retreats and Sales Representatives to advance deals.
• Design event itineraries based on client objectives and preferences.
• Guide clients throughout the pre-booking journey and support decision-making.
• Request quotes from venues and suppliers, compare options, and negotiate rates.
• Present well-structured recommendations and ensure alignment with client needs.
• Negotiate contract terms in the best interest of your client and TeamOut.
• Maintain accurate documentation and ensure smooth handoff to internal teams.

Preferred Qualifications

• Experience as a meeting planner, travel agent, concierge, or event planner.
• Strong communication and client-facing skills.
• Comfortable working with quotes, vendors, and basic budget considerations.
• Highly organized with strong attention to detail.
• Able to work independently in a fast-paced, remote-first environment.
• Interest in international destinations and retreat planning.
• Availability to work US time zones.

Why Join TeamOut

• Fully remote role
• Flexible time off
• Work with a YC-backed, fast-growing startup
• Annual team retreats
• Commission-based role with consistent earning potential
• Opportunity to contribute meaningfully to the future of corporate offsites

Equal Opportunity Statement

• TeamOut is an equal opportunity employer. We celebrate diversity and are committed to creating an inclusive environment for all contractors and applicants.

You’re also welcome to send your resume/portfolio to [email protected], along with a brief introduction about yourself and why this role interests you.