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

Pipeline Management

• Own and manage the reservation sales pipeline from initial inquiry through confirmed booking.
• Maintain accurate and current pipeline records in Streamline VRS and Conduit.
• Prioritize leads and ensure consistent follow-up across phone, email, text, and other approved channels.
• Improve inquiry-to-booking conversion, average booking value, and overall reservation revenue.
• Generate regular pipeline reports, forecasts, and performance summaries for leadership.
• Identify gaps in the sales process and recommend improvements to increase efficiency and conversion.

Team Leadership and Management

• Lead, coach, and develop Vaaraway's Guest Sales team, including international teammates, as the organization expands.
• Establish and monitor expectations for response time, follow-up activity, conversion, booking revenue, communication quality, and guest service.
• Conduct regular team meetings, one-on-one coaching, call reviews, and performance evaluations.
• Recruit, onboard, and train new sales team members while maintaining consistent standards across markets and time zones.
• Coordinate weekday, weekend, holiday, and peak-period coverage to ensure timely responses to sales inquiries.
• Develop repeatable training materials, sales scripts, standard operating procedures, and performance scorecards.
• Promote clear communication and a collaborative culture across geographic and cultural differences.

Escalations and Guest Retention

• Handle guest escalations with urgency, professionalism, and a resolution-first mindset.
• Lead the Vaaraway Return Campaign by proactively contacting past guests to generate repeat bookings.
• Identify at-risk reservations and develop strategies to recover bookings and retain revenue.
• Coordinate with internal teams to resolve concerns before they result in lost business.
• Identify recurring guest concerns and provide actionable feedback to leadership and Operations.

Sales Coverage and Support

• Provide inside sales support during standard operating hours, Monday through Friday.
• Maintain scheduled weekend availability to support active inquiries and peak booking periods.
• Serve as backup for primary sales coverage during off-hours, absences, and high-demand periods.
• Assist guests with property selection, availability, pricing, amenities, policies, and destination questions.
• Use a consultative sales approach to match guests with the most appropriate Vaaraway property.

Cross-Functional Partnership

• Build a strong working relationship with the Operations team, partnering closely with Jessica to create seamless guest and owner experiences.
• Collaborate with Marketing on promotions, market positioning, outreach, and lead-generation initiatives.
• Partner with the Revenue team on pricing strategy, availability optimization, booking restrictions, and demand forecasting.
• Communicate guest feedback, sales barriers, and demand trends to the appropriate departments.
• Attend internal team meetings, sales reviews, training sessions, and strategy discussions.
• Ensure reservation details, guest expectations, and special requests are accurately communicated to Operations.

Training and Portfolio Knowledge

• Facilitate sales training for newly onboarded properties, including selling points, guest profiles, property standards, and platform requirements.
• Develop and maintain a deep understanding of the Vaaraway portfolio and its destinations.
• Create property talking points, objection-handling guidance, and guest communication templates.
• Contribute to sales-strategy development, including market-specific approaches for key U.S. feeder markets.
• Stay informed about new properties, portfolio updates, promotions, seasonal opportunities, and destination demand.

Technology and Systems

• Manage and master Vaaraway's core sales platforms, including Streamline VRS, Conduit, and Claude AI.
• Use AI tools to improve guest outreach, pipeline analysis, call preparation, follow-up, and communication.
• Maintain complete notes, tasks, communication records, and booking information within company systems.
• Identify opportunities to improve sales workflows through technology and automation.
• Assist with testing, documenting, and implementing new sales tools and processes.

Field and Listing Quality

• Conduct periodic property visits and listing audits to verify accuracy, quality, and sales readiness.
• Review listings for accurate amenities, descriptions, photography, policies, and guest-facing information.
• Identify issues that could negatively affect guest confidence, conversion, or booking revenue.
• Provide actionable feedback to Operations and property owners to improve property presentation and sales performance.

Sales Projects and Expansion

• Support special sales initiatives, portfolio growth opportunities, and company expansion projects.
• Contribute to Vaaraway's continued growth in Costa Rica and other developing markets.
• Assist with market research and entry strategies for new geographic areas.
• Develop sales messaging and outreach strategies tailored to new destinations and guest segments.

Required Qualifications

• At least three 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.
• Hybrid in Sarasota, Florida