Guest Sales Manager
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.
Cook up 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.
Able 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.
Able to interpret pipeline data, prepare performance reports, and use findings to guide sales activity.
Able 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
Remote, USA; Preferred location near Sarasota, Florida