Bookings & CX Lead – Creative Travel

Job Type: Location Type: Remote: open to all US residents

 

Remote | Full-time Contract to Employee | Global Hours
Compensation: $60K-$70K base + equity + perks

This is not a traditional CX role.
This is for someone who thrives at the intersection of craft, design, travel, and tech-and wants to lead, build, and change lives through creativity.

VAWAA (Vacation With An Artist) is a curated platform where creatives book mini-apprenticeships with master artists around the world. From Japanese calligraphy to Moroccan textiles, guests join artists in their studios to make, learn, and be transformed.

We’re looking for a sharp, detail-driven Bookings & CX Lead to own our guest experience-from first inquiry to post-trip follow-up.

You’ll drive bookings, guide guests through complex journeys, and ensure every traveler feels seen, supported, and inspired.

This role requires monitoring global guest communications across time zones, including early mornings, evenings, and weekends. It’s not for everyone-but if you’re energized by autonomy, creativity, and deep human connection, it might just be your dream role.

Who You Are

You’ve experienced the power of immersive craft-whether apprenticing with a master, running creative retreats, or curating experiences that shift perspectives. You’re the go-to person in a crisis, on top of every detail, and oddly thrilled by inbox zero.

You’re tech-fluent-you know how to scale that care remotely. You’re not a developer, but CRMs, automations, and operations dashboards don’t scare you. You’ve probably worked at a creative or mission-driven startup before, where “other duties as assigned” included just about everything. You’re resilient, hungry, and energized by complexity, chaos, and the chance to make a real impact.

What You’ll Do

• Sales: Own the conversion funnel. Respond quickly to booking inquiries, understand guest needs, and turn interest into paid bookings.
• Guest Experience: Be the single thread from pre-booking to post-trip. Anticipate issues. Troubleshoot with grace. Ensure every guest feels seen, supported, and inspired.
• Operations: Coordinate with 160+ artists in 30+ countries. Monitor emails at odd hours. Stay ahead of the curve on scheduling, payments, and logistics.
• Craft Fluency: Have fluency in global crafts and creative practices so you can speak with authority when guiding guests.
• Data & Process: Improve our processes, from CRM workflows to post-trip follow-ups. Use AI, and other tools like Streak, Customer.io, Zapier, or Notion to streamline and scale our workflows.

Requirements

• 2+ years in entrepreneurship, online customer experience, operations, sales at a creative startup
• Strong English writing and communication skills
• Digital fluency (AI, CRM, automations, customer platforms)
• Deep curiosity for global arts, culture, and creative process
• International solo travel experience
• Willingness to monitor messages and respond quickly-including weekends and off-hours when needed.

You might be answering a guest question before breakfast, troubleshooting a payment issue while chatting with an artist in Oaxaca, updating an automated flow in Customer.io, or checking in with a ceramicist in Japan late at night.

Nice to Have

• Ex-entrepreneur or built high touch CX at a boutique consumer startup
• Familiarity with global crafts or art forms
• Proficiency in multiple languages
• Experience working directly with artists or cultural institutions

Why Join Us?

We’re small, scrappy, and mission-driven. We’re creating space for people to unplug, reconnect with their creativity, and learn from masters of their craft. You’ll work closely with our founder and artists in 30+ countries. This is a rare opportunity to build something meaningful-and help others do the same.

This role starts as a full-time contract position. After 4 months, you’ll transition to full-time employee status with:

• Equity or profit sharing options – earn from what you help build, with options or revenue share upon profitability
• Health insurance
• 1 Free and discounted VAWAA experiences
• Daily connection with global artists + a mission that matters

Growth path: In 2-3 years, this role could evolve into Head of Guest Experience, Head of Creative Operations, or even COO, depending on your skills and ambition.

Sound like you?

Apply with a short note on why you’re excited, and tell us about a time you made magic happen for a guest or client.

We are based in New York, but open to remote applications from within the US, Canada, Western Europe.

Tip: Cover Letters that include a link to a short 5 min video explaining why you are the best person for this role will be given preference.

As a Equal Opportunity Employer, VAWAA will consider all qualified applicants regardless of color, ancestry, religion, sex, national origin, sexual orientation, age, citizenship, marital or family status, disability, gender identity or expression, veteran status, actual or presumed belonging to an ethnic group, or any other legally protected status. If you have a disability or special need that requires accommodation, please let us know.