[Hiring] Guest Sales Manager @Better Talent

Role Description

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.

• 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.
• Combine strategic leadership with hands-on selling, using data, technology, and coaching to improve conversion rates, increase repeat business, and create memorable guest experiences.
• Thrive in a fast-paced, goal-oriented environment and enjoy collaborating across departments.
• Play a key role in shaping our sales strategy, developing high-performing team members, and helping drive the company's continued growth.

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.

Requirements

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

Benefits

• Annual Salary: $60,000
• On-Target Earnings: Approximately $80,000 - $88,000 annually based on bonus achievement.
• 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.