About the Role We're hiring a Remote Guest Services & Sales Representative for a premier short-term rental management provider based in Southeastern Wisconsin. We are looking for a highly communicative service-driven professional who can provide excellent guest support while helping convert inquiries into confirmed bookings. This role is ideal for someone with strong hospitality reservations or customer service experience who is confident speaking with guests managing booking details and resolving concerns professionally. The role supports evening and weekend guest services reservations and sales operations in a fully remote independent contractor arrangement. Key Responsibilities Respond to guest inquiries through phone email and chat in a professional and timely manner. Provide accurate property information highlight amenities and guide guests through the booking process. Convert qualified inquiries into bookings through clear communication strong follow-up and a guest-focused sales approach. Upsell relevant services offers or add-ons when appropriate. Manage reservations in the booking system and ensure guest details reservation notes and communications are accurate. Process booking changes modifications and payment-related steps according to company procedures. Document guest interactions requests concerns and resolutions in the appropriate system. Coordinate with operations and maintenance teams to support smooth guest stays and property turnovers. Resolve guest issues with empathy professionalism and timely follow-through. Escalate complex concerns to management while maintaining ownership of the guest experience. Qualifications Required 3+ years of experience in hospitality hotel front desk reservations guest services short-term rentals or a similar customer-facing role. Strong verbal communication skills with a clear confident and professional phone presence. Strong written English communication skills for guest support through email and chat. Experience with sales upselling reservations or revenue-focused guest interactions. Strong attention to detail and ability to manage guest information accurately. Comfortable working independently in a remote environment. Able to stay calm professional and solution-oriented when handling guest concerns. Reliable internet connection and a quiet professional remote work setup. Preferred Experience using Cloudbeds or similar reservation/property management software. Familiarity with short-term rental platforms such as Airbnb Vrbo or Booking.com. Experience supporting short-term rental vacation rental or property management operations. Experience using CRM helpdesk or guest communication tools. Work Schedule Required schedule Monday Friday Saturday and Sunday 500 PM to 100 AM CST. Candidates must be available for evening and weekend guest support. Holiday availability may be required depending on business and guest needs. Compensation $5 USD per hour. Ongoing training and support will be provided. Long-term growth opportunities may be available based on performance reliability and business needs. What Success Looks Like The ideal candidate communicates confidently builds trust quickly with guests and consistently turns inquiries into positive booking experiences. This person is organized proactive calm under pressure and able to balance hospitality sales reservation accuracy and issue resolution in a remote environment. How to Apply Please apply directly through Indeed using the Apply button and include an updated resume. Pay Php310.00 per hour Benefits Work from home Application Question(s) How many years of experience do you have in hospitality guest services reservations hotel front desk or short-term rentals? Are you available to work Monday Friday Saturday and Sunday from 500 PM to 100 AM CST? What reservation property management CRM or guest communication tools have you used? Work Location Remote