Director of Wedding Bookings
About the Role
We are hiring a Director of Wedding Bookings, a high-ownership operator who will oversee all incoming communication channels, manage the couple experience from first contact to booked stay, and ensure the highest standards of responsiveness, clarity, and conversion.
This is a pivotal revenue-driving role with massive growth opportunity as WedStay becomes a growing international brand.
The Director of Wedding Bookings owns the entire front end of the WedStay couple journey. You will manage all communication touchpoints, oversee AI-assisted tools, pre-qualify couples, conduct initial discovery calls, and guide them toward booking the perfect WedStay property.
You are responsible for ensuring that every conversation on our platform feels exceptional, helpful, elevated, and consistent. This is a fast-paced, performance-oriented role with significant upside and long-term leadership potential.
Responsibilities
- Lead all couple communications — manage text, email, and chat inbox with timely, warm responses
- Oversee AI and automated conversation tools — monitor and refine AI-driven chat interactions
- Drive conversion & booking performance — guide couples through property details and track conversion rates
- Conduct pre-qualification & discovery calls — assess fit, answer questions, explain how WedStay works
- Own customer experience — ensure couples feel supported and identify friction points
- Cross-functional collaboration — work with marketing, product, vendor and property teams
Requirements
- Wedding industry experience highly preferred; hospitality experience required
- 3–7+ years in customer success, sales, hospitality, or similar communication-heavy roles
- Demonstrated experience in managing high-volume customer conversations
- Strong verbal communication — especially on pre-qualification or discovery calls
- Comfortable using CRM systems, automations, and AI communication tools
- Ability to track and report on conversion data and performance metrics
- Exceptional organization and multitasking skills
Benefits
- Base salary plus performance-based compensation
- Rapid growth opportunity into senior leadership roles
- Direct ownership of the booking pipeline
- Remote/Hybrid flexibility
- Join a fast-growing international brand
Ready to apply?
Join our team and help couples create unforgettable wedding experiences.