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The whole team by the pool at the 2026 retreat, one silhouette left open

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Independent Trip Designer

We turn hospitality professionals into independent Trip Designers who sell corporate retreats.

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  • Independent Trip Designer
  • Commission on every deal, paid at signature
  • Remote, US time zones
  • 8 questions, about 2 minutes
Your name
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The offer

Bring the deal. Get paid at signature.

For people with hotel, events or travel experience, based in the US, Canada, Mexico or the Caribbean and working US time zones.

What you do
Find companies planning offsites and sign them with TeamOut.
How you earn
Commission on every deal, no cap. Your first payout comes at signature.
How you work
Independent, fully remote, on your own schedule.
Read the full offer

  • The role

    Independent Trip Designer is a sales role first. You find companies planning offsites, leadership summits, sales kickoffs and conferences, and sign them with TeamOut. You build the venue shortlist, the quote and the contract in our tools, and our planning and production teams take the event from there.

  • Who you sell to

    The people responsible for bringing their teams together: executive assistants, chiefs of staff, People and Operations leaders, founders. Most of them were never trained to plan events, and that's exactly where you come in. Companies like OpenAI, Anthropic, Netflix and Airbnb already run their offsites with TeamOut. A retreat is the rooms, the meeting space, the dinners and the activities in one deal, and many companies book again the next year.

  • How you work

    You work as an independent contractor. Fully remote, on your own schedule, on US time zones. You find the company, build the relationship and sign the deal. Our teams handle venue sourcing, contracts, billing, commission collection and production.

  • How you earn

    Commission on every deal you close, with no cap. Your first payout comes at signature, when the client signs the contract. TeamOut handles billing and collects the commission for you.

  • What you get

    • Founder-led training, in person
    • Online training modules you follow at your own pace
    • Built-in business intelligence and our internal prospecting tools
    • A TeamOut email address and the full tech suite
    • Company retreats, FAM trips and industry events

  • Who it's for

    A background in hotels, events or travel, in any role. An appetite to sell, ideally with something you've already sold. You live in the US, Canada, Mexico or the Caribbean.

About TeamOut

The experience behind better company moments

TeamOut helps companies bring people together better. Offsites, leadership summits, sales kickoffs, conferences: the moments that shape a company's culture.

Most of the people planning them were never trained to, so we put real industry experience on their side. Our team comes from inside hospitality: hotels, venues, production, events and technology. We've sat on the other side of the table. Now we sit on our clients'.

backed by Y Combinator
YC W22
managed on behalf of our clients
$80M+
certified travel company
IATA
Dinner on the beach at the 2026 company retreat in Puerto Escondido
We hire the best people from hospitality. An industry that historically demands the most rigid schedules and the least flexibility of almost any sector. If we wanted those people to do their best work, we couldn't just offer a job. We had to offer a different kind of work life.
Thomas Mazimann, Co-founder and CEO, TeamOut

Trusted by teams at

  • OpenAI
  • Anthropic
  • Netflix
  • Airbnb
  • Reddit
  • Shopify
  • L'Oréal
  • Brex
  • Accenture
  • Kayak
  • PwC
  • Product Hunt

What you get

What makes it worth it

  • Earn what you bring

    Paid at signature. Almost nobody in this industry does that.

    • Commission on every deal, no cap.

    • Corporate groups are large, and many book again the next year.

    • Every event can grow: activities, production, premium services.

  • Your business, your rules

    • Action. Pick your market, your channels and your pitch.

    • Location. Home, a hotel lobby or the road. Fully remote.

    • Schedule. No hour-tracking, no micromanagement. Build your week around your life.

  • You sell, we run the rest

    • You: find the company, build the relationship, sign the deal.

    • Us: venue sourcing, contracts, billing, commission collection, production.

    • Nobody hands you leads, but you never prospect blind: built-in business intelligence and our internal tools.

  • We train you to sell retreats

    • Online training, at your own pace. Prospecting, outbound, negotiation, how to run a deal with TeamOut. Short modules, real playbooks.

    • Founder-led training, in person. Live sessions with the people who built the company.

The people

Join a team of 50+ Independent Trip Designers

We run on trust. You work on your own terms, never alone.

Remote all year. One week a year, the whole company gets together somewhere worth flying for. We believe what we sell: teams are better when they spend real time together.

See the team on Instagram
The team at a white night party during a retreat

  1. 2025

    Guatapé, Colombia

    A week at The Brown, on the lake outside Medellín. Team sessions in the morning, a hike, a day on the water, three themed dinners.

  2. 2026

    Puerto Escondido, Mexico

    One private hotel on the Pacific coast, full buyout. Work sessions under the palapa, then surf, yoga, breath work and cold plunges.

  3. All year

    Between retreats

    Thomas, Maddie and Natalie at ProcureCon Travel 2026The team at a hospitality trade show

    FAM trips to discover the venues you'll sell, industry events like ProcureCon, and a team that answers on Slack when a deal gets complicated.

Questions, answered

  • Is there a base salary?

    No. It's commission only, with no cap.

  • When do I get paid?

    Your first payout comes at signature, as soon as the client signs the contract. TeamOut collects it and pays you.

  • Will TeamOut give me leads?

    No, leads are not provided. You find the accounts yourself, with TeamOut's built-in business intelligence and our internal tools.

  • Do I need sales experience?

    It helps a lot. Most of the team came from hotels, events or travel and had already sold something: rooms, packages, sponsorships. We train the method, you bring the appetite.

  • Do I need hospitality experience?

    Yes. Any role in hotels, events or travel counts.

  • Where can I be based?

    The role is fully remote. You need to live in the US, Canada, Mexico or the Caribbean and work on US time zones.

Ready to apply?

Eight questions, about two minutes.

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