Customer Service Representative 

Department: Customer Service 

Reports To: Head of Customer Service 

Location: Remote, all 50 US states 

Job Type: Full-Time 

FLSA Classification: Non-Exempt 

Job Brief: 

The Customer Service Representative is responsible for delivering exceptional customer service and ensuring a seamless and exceptional experience for both travelers and hosts. The ideal candidate will possess a strong background in hospitality, ideally within the vacation rental management sector, and have a genuine passion for customer satisfaction. This position will play a key role in supporting the launch of our new business segment targeting individual property owners (“hosts”), driving the development of tools and processes to cater to this unique customer base. Duties include explaining features and services, fielding issues between travelers and hosts, troubleshooting technical issues with our Engineering team, and collaborating with Operations, Product and Account Management teams. 

Responsibilities: 

• Ensure optimal experiences for Whimstay customers, resolving any issues that arise.  
• Monitor and respond to customer inquiries via phone calls, emails, and texts. 
• Drive system structure and support for the upcoming launch of a new business segment focused on individual property owners or “hosts.” 
• Document conversations and actions using our integrated CRM system. 
• Document traveler inquiries and issues, pass along needed information and communications to management, and manage follow-up.  
• Innovatively forecast customer needs and devise creative solutions to emerging challenges. 
• Support the execution of processes and strategies to enhance the customer experience. 
• Represent the “voice of the customer” and provide feedback for incorporating on-going product enhancements and fixing issues. 
• Review and respond to customer surveys. 
• Review bookings for fraud risk. 
• Research and review payment attempts and reach out to customers as appropriate. 
• Research technical issues and irregularities and collaborate on troubleshooting in partnership with Head of Customer Service, the Product Team and the Engineering Team with a goal of improving our platform. 
• Provide valuable feedback to management to continuously improve customer service policies and procedures. 

Requirements: 

• 4+ years’ experience working in customer service, customer success, or related role. 
• Experience in the vacation rental market is highly desirable. 
• Comprehensive understanding of both the host and traveler sides of our customer base, with a strong desire to find mutually beneficial solutions. 
• Versatility in handling various issues, effectively balancing the needs of travelers and hosts. 
• Excellent written and verbal communication skills. 
• Familiarity with CRM systems and practices; ZenDesk is a plus. 
• Excellent computer skills, including MS Office tools and applications. 
• Customer orientation and ability to adapt/respond to different personalities. 
• Strong attention to detail. 
• Ability to multitask, prioritize, and manage time effectively. 
• Self-starter with good decision-making skills; can operate independently within loosely-established guidelines. 
• Ability to thrive in a start-up environment, including accepting frequent change, thinking on your feet, and possessing strong flexibility. 
• Excited about joining a startup culture and the opportunity to work in an emerging vertical in a burgeoning market – prior startup experience is a plus. 

Language: English: Fluent; Spanish: Fluent is an added bonus 

About Whimstay: 

Whimstay is the leading vacation rental marketplace for travelers looking for the best deals on last-minute stays. We offer exclusive discounts on properties that might otherwise go unrented while driving incremental revenue for hosts. Whimstay delivers a best-in-class user experience via a mobile app and web and provides top-notch customer support, making it easy to book on a whim! 

Schedule: Monday-Friday, but may require after-hours, weekend, and holiday work.  

Travel: 0% 

Pay Range: $50,000 – $60,000 per year 

Benefits: 

• Unlimited PTO  
• Health, dental, and vision insurance 
• Equity package 

Whimstay is an equal opportunity employer. We do not discriminate on the basis of race, color, religion, sex, sexual orientation, gender identity or expression, national origin, age, disability, veteran status, or marital status.