Remote Digital Guest Experience Manager

About VAWAA

At VAWAA.com (Vacation With An Artist), we are on a mission to offer immersive, one-on-one creative experiences with master artists from around the world. In an increasingly digital world, VAWAA provides a unique opportunity to connect with global artists, learn traditional crafts, and experience local cultures first-hand. Our goal is to honor and celebrate craft while helping master artists pass down their knowledge to future generations, making a small but meaningful contribution to preserving these timeless traditions. We’ve curated over 150 artists across 35 countries, offering life-changing travel experiences that feed creativity and nourish the soul.

We are assembling a team of agile, culturally fluent, entrepreneurial-minded talent to craft the vision strategy and tactics to help scale the brand.

Role Overview

The Digital Guest Experience Manager is a dynamic opportunity for a people-driven, entrepreneurial individual to shape exceptional end-to-end experiences for VAWAA guests globally. Working closely with the Founder and team, you’ll play a key role in facilitating transformative creative journeys for our customers. Your focus will be on converting online inquiries into bookings, offering personalized guidance, and managing communications from pre- to post-VAWAA. This includes processing bookings, handling payments, and providing follow-up support. The ideal candidate will bring a blend of sales expertise, creativity, cultural fluency, and business acumen to deliver a seamless, world-class service to our guests.

What we’re looking for

• Experience: You’ve spent at least 2 years in a B2C digital customer service role at an early-stage or fast-growing startup.
• World Traveler: You’ve traveled solo, navigate new places and languages with ease, and make friends wherever you go. Unexpected challenges? You handle them like a pro.
• Lifelong Learner: You’re constantly signing up for immersive experiences and driven by creating exceptional moments for others.
• Customer Advocate: You intuitively understand the hesitations around booking big trips online and know how to guide, motivate, and reassure people through the decision-making process.
• Clear Communicator: You have the ability to convey complex information simply and accurately, while adapting tone to diverse guest needs. You write persuasively and with precision.
• Tech-Savvy: A digital native, you leverage technology to work smarter, engage online, and solve problems efficiently.
• Problem Solver: You anticipate issues before they arise and can confidently tackle unexpected challenges with resourcefulness.
• Detail-Oriented: Ultra-organized with a strong operational mindset. You create systems to streamline tasks and never miss a detail—balancing quality and speed effortlessly.
• Cultural Knowledge: You’re familiar with global arts, design, crafts, and cultural trends.
• Work Ethic: Self-starter, hardworking, and impact-driven. No complainers here—we want someone ready to step up and make things happen.
• Flexibility: With customer inquiries driving our 7-day-a-week business, you’re willing to cover as needed and committed to timely responses.

What you’ll do

• Facilitate life-changing travel and creative experiences across the globe.
• Leverage your sales skills to convert inquiries into bookings, providing personalized guidance and follow-ups throughout the decision-making process.
• Manage communications with multiple customers at various stages—from initial inquiry to post-experience—using smart tools to ensure timely, accurate responses without missing any details.
• Coordinate booking-related communication with artists across time zones, ensuring seamless collaboration.
• Process, confirm, and manage all customer bookings, payments, refunds, rescheduling, cancellations, promo codes, and gift cards with precision through our backend systems.
• Identify upsell opportunities to maximize customer value.
• Prepare customers with essential pre-travel information and resolve any individual issues that arise.
• Collect and organize post-experience feedback, photos, and reviews to foster repeat customers and referrals.
• Surpass customer expectations, consistently delivering an extraordinary experience.
• Build lasting relationships within the VAWAA community, creating loyal, long-term customers.
• Collaborate with the Marketing Manager to showcase customer stories and highlight positive experiences.
• Monitor key metrics, providing feedback and actionable insights to improve customer experience and operational efficiency.
• Optimize the booking flow to minimize friction and scale operations while maintaining human and personalized touches.
• Work efficiently with daily tools such as Slack, Streak, Customer.io, Notion, Google Documents, Trello, and Mailchimp.

What you can expect

• Mission-Driven: We are leading the way in crafting the best creative experiences. Growth will be thoughtful but urgent.
• Core Team Impact: You’ll be part of the core team shaping VAWAA’s future and direction.
• Curiosity & Creativity: Our culture values curiosity, creative thinking, and constant learning—fostering an environment of excellence.
• Ownership & Accountability: We lead with optimism, tenacity, and courage—taking ownership at every level.
• Perks & Benefits: Health and dental benefits, a complimentary VAWAA experience each year, and company swag.
• Global Community: Be part of a creative, global community of artists, makers, and diverse thinkers.
• Compensation: $55K–$65K based on experience, plus stock options. For experienced candidates, we can discuss additional equity compensation.

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

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.

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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.