Customer Service Representative

Whimstay is the leading vacation rental marketplace for travelers looking for the best deals on last-minute stays. The Customer Service Representative is responsible for delivering exceptional support to travelers and hosts, ensuring a seamless booking experience by resolving inquiries and issues, and collaborating with various teams.

Responsibilities:

• Monitor and respond to customer inquiries via email, live chat, SMS, and phone
• Resolve issues for both travelers and hosts promptly and professionally, managing follow-up as needed
• Accurately document conversations and actions in our help desk (Intercom) and complete associated tasks
• Prioritize individual goals with broader strategic objectives that contribute toward the Customer Service team’s KPIs and metrics
• Escalate complex or sensitive situations to the Head of Customer Service with clear context and documentation
• Surface patterns in customer feedback and communicate them to support ongoing improvements
• Support the execution of customer experience processes and business strategies aligned with company goals
• Represent the voice of the customer by sharing product feedback with relevant teams
• Review bookings for fraud risk, investigate payment issues, and reach out to customers as needed
• Collaborate with the Head of Customer Service, Head of Customer Experience, Product, and Engineering to investigate and troubleshoot platform issues

Requirements:

• 3+ years of experience in customer service, customer support, or a related role
• Must be available to work full time within the hours of 10 a.m. to 8 p.m. PT, including full weekend availability; potential schedule once training is complete: Wednesday – Sunday or Thursday – Monday
• Excellent written and verbal communication skills
• Familiarity with help desk systems; Intercom experience is a plus
• Strong computer skills, including comfort with technical troubleshooting and bug reporting
• Self-starter who can work independently within established guidelines
• Highly organized with strong attention to detail
• Able to multitask, prioritize, and manage time effectively in a fast-paced environment
• Comfortable in a startup environment — adaptable, flexible, and calm under change
• Reliable high-speed internet connection and a quiet home workspace without distraction required
• English fluency required
• Prior startup experience is a plus
• Experience in the vacation rental or short-term rental market is a plus; ability to balance the needs of both travelers and hosts with empathy and fairness
• Spanish fluency is a plus