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.

Position Summary

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.

Key Responsibilities

Sales & Pipeline Management

• 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.

Team Leadership & Guest Experience

• 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.

Sales Strategy & Collaboration

• 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.

Technology & Growth

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

• Support portfolio growth, special sales initiatives, and expansion into Costa Rica and other developing markets.

Required Qualifications

• At least two years of professional experience in reservation sales, hospitality sales, vacation rentals, hotels, travel, inside sales, or a related field required.

• At least one year of experience managing, supervising, or coaching a sales, reservations, or customer-service team.

• Demonstrated experience managing a sales pipeline from initial inquiry through conversion.

• Proven success working toward measurable booking, sales, revenue, retention, or conversion goals.

• Experience using a CRM, property-management system, reservation platform, or comparable pipeline-management technology.

• Strong written and verbal communication skills in English.

• Experience handling guest or customer escalations professionally.

• Ability to manage and communicate effectively with teammates working internationally and across different time zones.

• Strong organizational skills and the ability to manage multiple leads, priorities, deadlines, and follow-up activities.

• Ability to interpret pipeline data, prepare performance reports, and use findings to guide sales activity.

• Ability to periodically visit Vaaraway properties for listing and sales-readiness audits.

• Reliable internet access and a professional workspace when working remotely.

Compensation & Benefits

Annual Salary: $60,000

Bonus & Commission

In addition to base salary, this role offers multiple opportunities to earn additional compensation based on individual and company performance:

• On-Target Earnings: Approximately $80,000 - $88,000 annually based on bonus achievement

Benefits

• Comprehensive medical, dental, and vision insurance

• Life insurance

• Paid time off, including vacation and sick leave

• Workplace perks including food, coffee, and team activities

• Opportunity to grow alongside a rapidly expanding hospitality company

Schedule

• Tuesday–Saturday | 9:00 AM–5:00 PM; Consistent Sundays and Mondays off.

• Remote, USA; Preferred location near Sarasota, Florida