Guest Sales Manager

Company Overview

Vaaraway is a modern vacation rental management and marketing company built to help property owners increase bookings, improve guest communication, and grow rental revenue through a more flexible and performance-driven approach. We support owners and lodging partners with professional listing strategy, dynamic pricing, multi-channel marketing, guest sales support, reservation management, and performance reporting, giving them access to a stronger sales and revenue platform while allowing them to keep the local teams and personal hospitality style that make their properties unique.

Working at Vaaraway is an opportunity to be part of a growing brand in the luxury vacation rental space where sales, hospitality, technology, and guest experience all come together. Our team is building a smarter, more scalable way to support owners and serve guests across exciting vacation markets, including coastal destinations, boutique lodging communities, and international growth opportunities. This is a great role for someone who enjoys a fast-moving environment, wants to make a direct impact on revenue and guest satisfaction, and is excited to help shape the systems, service standards, and sales strategies of an emerging hospitality brand.

Vaaraway is seeking an ambitious and relationship-driven Guest Sales Manager to lead our reservation sales operation and help accelerate the growth of our luxury vacation rental portfolio. This is an opportunity for a natural sales leader who enjoys building relationships, influencing decisions, coaching others, and turning opportunities into measurable results. In this role, you'll own the guest sales journey from the first inquiry through booking while leading a growing reservations team focused on delivering exceptional service and maximizing revenue.

You'll combine strategic leadership with hands-on selling, using data, technology, and coaching to improve conversion rates, increase repeat business, and create memorable guest experiences. Success in this position requires someone who thrives in a fast-paced, goal-oriented environment, enjoys collaborating across departments, and is energized by exceeding targets. As Vaaraway continues to expand into new destinations and markets, you'll play a key role in shaping our sales strategy, developing high-performing team members, and helping drive the company's continued growth.

• Own the reservation sales pipeline from initial inquiry through confirmed booking, ensuring timely and consistent follow-up.
• Drive improvements in conversion rates, average booking value, repeat business, and overall reservation revenue.
• Maintain accurate pipeline activity in Streamline VRS and Conduit and provide regular sales forecasts and performance reporting.
• Use a consultative sales approach to understand guest needs, recommend the right properties, overcome objections, and convert inquiries into bookings.

• Lead, coach, and develop Vaaraway's growing Guest Sales team, including international team members across multiple markets and time zones.
• Establish and monitor performance expectations for response times, follow-up, conversion, booking revenue, communication quality, and guest service.
• Conduct regular coaching, call reviews, training, and performance evaluations while supporting the recruitment and onboarding of new team members.
• Coordinate sales coverage across weekdays, weekends, holidays, and peak periods and provide hands-on sales support when needed.
• Handle escalated guest concerns and lead retention initiatives, including Vaaraway's Return Campaign, to protect revenue and generate repeat bookings.

• Partner with Operations, Marketing, and Revenue Management to align guest expectations, promotions, pricing, availability, and booking strategy.
• Maintain strong knowledge of Vaaraway's properties and destinations and ensure the sales team is prepared to confidently sell new and existing inventory.
• Develop sales scripts, property talking points, objection-handling strategies, training materials, and guest communication standards.
• Conduct periodic property and listing audits to identify opportunities to improve guest confidence, conversion, and booking performance.

• Leverage Streamline VRS, Conduit, Claude AI, and other technology to improve sales workflows, guest outreach, reporting, and team efficiency.
• Support portfolio…