Experience Operations Lead (Guests & Artists)

Do you love operations & metrics as much as you love creative travel? Are you energized by helping unlock life-changing experiences for others? Then read on...

AI, screen fatigue, and loneliness are pulling people back toward the analog world, and rapidly increasing the value of human creativity. At the same time, AI is making it possible to scale a deeply human company in a way that was not possible before.

It’s a global platform where people travel to learn directly from master artists in their studios for multi-day apprenticeships. Stepping into the real rhythm of their practice and leaving changed. We are defining a new category at the intersection of travel, creativity, learning, culture, and transformation.

VAWAA artists are extraordinary ceramicists, painters, weavers, chefs, sculptors, shoemakers, woodworkers, designers, and indigenous makers around the world.

Our guests are curious humans who want to make something with their hands, learn from someone extraordinary, and experience a place through its creative culture.

95% of our guests describe their experience as life-changing. 98% of the VAWAA artists have stayed on the platform. People come to us when they want something more meaningful than another vacation.

Demand is outpacing supply. On the other hand, we have 1200 artists on the waitlist. Our team is small (just 5) and we’re just trying to keep up with the demand. We’ve built a really good product. Our founder built VAWAA after two decades in design and tech, and a life built around learning and traveling across 65+ countries. Our angel investors are great too, and repeat VAWAA guests.

If you’ve played the startup game before, you know that nothing in life is certain. That said, we have strong fundamentals, we believe our mission for human creativity is meeting the moment, and our business is working.

A guest in New York wants to learn weaving in Oaxaca. 
An artist in Japan needs help understanding a special booking request.
A solo traveler is excited but nervous.
A guest who is a well known illustrator wants to learn a specific calligraphy technique.
An artist in Mexico needs help restructuring their VAWAA experience.
A VIP guest wants to feel this will meet their standards.
A retiree has questions about stairs and accommodations.
A guest is almost ready book, but needs the right nudge.
An artist has moved studio location and needs photo & logistical updates.

We continuously improve experience with guests and artists giving feedback after every VAWAA. We observe, track and learn from guests and artists daily.

We build and optimize systems, workflows, templates so we can operate with speed and clarity. We believe delivering a great experience consistently requires a very organized backstage.

A 10-star beautiful trip depends on 57 tiny details not falling through the cracks.

We want an ambitious, compassionate, detail-oriented do-er who can own the day-to-day human experience across both sides of VAWAA- guests and artists. Someone who loves trying new things, has operational stamina, moves quickly, and wakes up each morning energized by this stuff.

As the company evolves, this role may lean more toward artist onboarding, experience design, or guest operations—depending on business needs. In all cases, you will own a core domain with autonomy and increasing strategic influence.

• Work closely with the founder and help scale the experience layer of VAWAA.
• Improve our booking conversions and optimize the funnel from inquiry to repeat guest.
• Monitor key metrics representing bookings, guest & artist health.
• Partner with guest experience manager to own the end-to-end guest journey managing bookings, decisions, experience issues, follow-ups, CRM hygiene, templates, workflows, and the SOPs that help us scale care without losing soul.
• Support artists with onboarding, gathering assets, offering guidance, co-designing, editing and support.
• Oversee where guests get confused, where artists need more support, where bookings stall, where the system needs to get smarter, facilitating product decisions.
• Solve time-sensitive issues across time zones, cultures and contexts.
• Maintain a great vibe and make the VAWAA experience better every week.
• Maintain responsiveness wherever guests and artists talk to us– primarily email, but also whatsapp and Instagram.
• Automate your own job without losing the human soul. AI is making it possible to scale a deeply human company in a way that was not possible before. Anything you find yourself doing over and over, it’ll be your job to automate.

If this range stresses you out, this may not be your role. If it sounds fun, keep reading.

• Are energized by helping unlock life-changing experiences for others
• Treat high-volume, high-context execution like a competitive sport, and get real satisfaction from nailing the details impeccably
• Live and breathe art, craft, culture, travel, and creative experiences 
  
• Bring a quantitative mindset to experience quality, conversion, and growth 
• Love setting ambitious goals and following through on them 
• Are comfortable with ambiguity, can change course fast, and learn quickly
• Get genuine satisfaction from a clean inbox, a clean CRM, and a well-run system 
• Use AI tools all the time and are excited to keep teaching yourself how to use them better 
• Are kind, thoughtful, tasteful, and fun to be around  
• Can respectfully challenge a decision and explain why

• 2-4 years of digital customer experience 
• Experience growing operations for an early customer base 
• Strong writing, editorial, visual, and experience-design skills 
• Minimum 2 years experience working full-time in remote, computer-based roles requiring responsiveness and self-direction 
• Have fluency in tools like Streak, Customer.io, Helpscout, Zendesk, Front, Notion, Slack, Google Workspace, AI tools. 
• Bonus if you have lived and solo traveled internationally

• You may have worked in guest experience, client experience, creative operations, marketplace operations or jack-of-all-trades-at-a-startup 
• Managed a high-volume inbox, bookings, logistics, CRMs, or international client communication
• Built your own projects, hosted gatherings, organized retreats, run workshops, created content, or made things with your hands
• Been part of the early growth stage of a successful startup in a community management, customer support/success or operations role

We are remote, but need New York working hours. 

VAWAA guests and artists are spread globally. We are a small team, so flexibility is needed on evenings and weekends when guest or artist issues come up.

Role begins as a 4-month full-time contract with intention to convert to full-time employee.

Comp. contract phase: $3,500–$5,000 per month, depending on capability and location.

Upon conversion to full-time:

• $65,000–$85,000 salary, depending on performance and location.
• 0.25%–0.5% equity or profit sharing options
• Health insurance
• 1 Free and discounted VAWAA experiences
• Work closely with our founder and community of artists and guests in 50+ countries + a mission that matters

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

We’re working toward an ambitious goal. If you’re looking for a comfortable, highly structured job, or one that feels exciting simply because it involves travel and art, this is probably not the role for you.

We’re building a global platform around human creativity in an AI world. Our work is emotional, logistical, cultural, and operational all at once. We operate across 42 countries and time zones, work with hundreds of artists and guests, and navigate all the beautiful complexity that comes with real humans, real travel, and real creative experiences.

There are no layers or places to hide. If something is broken, you’ll be expected to notice it, understand it, and help improve it. If guests keep getting stuck at the same point, you’ll help fix the journey. If artists need better support, you’ll help shape the system. If a workflow is messy, you won’t just complain about it. You’ll make it better.

We also care deeply about how people work. We value people who don't complain, keep commitments, ask clear questions, give direct updates, receive feedback without defensiveness, take responsibility when something slips, and learn quickly from mistakes. 

We’re remote, which requires trust, responsiveness, and strong follow-through. 

So if you want a neat playbook, a narrow lane, a lot of structure, or a job where someone else carries the emotional and operational weight, this is not it.

But if you’ve been wanting to dive into something meaningful, build from the inside, take real ownership, grow fast, and shape core functions at an early stage, this could be exactly the role you’ve been looking for.

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

Tip: For question 3 of the application, you’ll stand out if you include a link to video telling us why you want to do this and why we should hire you. Let us see your personality.

A quick note from me (founder):

I’ll be personally reviewing every application — and as a very small team juggling everything from fundraising to product to growth to support, my bandwidth is limited.

That said, this role is mission-critical. I'm eager to find the right person fast, and will reach out quickly if there's a potential fit.

I may not be able to respond to everyone, but I want to thank you in advance for your time, care, and interest in joining VAWAA. I’m excited to hear from you.