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