Customer Onboarding Team Leader

About The Position

Guesty is the all-in-one platform for short-term rental hosts to automate and optimize every aspect of their property management operations. With purpose-built technology, industry-wide expertise, and an R&D team of 250+ engineers, Guesty ensures that hospitality businesses can streamline and achieve growth while delivering the best value to guests. With a complete suite of features and 150+ industry partners, including major booking OTAs like Airbnb, Vrbo, Booking.com, Tripadvisor, Expedia, Hopper, Google Travel, and many more, Guesty is transforming the hospitality industry with innovative solutions. Today, Guesty has 15 offices and 700+ team members across the globe.

Our Guesty Lite team is on the lookout for an exceptional Customer Onboarding Team Leader to join us. Are you ready to take on a new challenge and make an impact? We'd love to hear from you!

Responsibilities

• Manage and oversee a team of Customer Onboarding Specialists, ensuring seamless team operations and a high standard of customer experience.
• Own shift planning and workload allocation, ensuring full coverage and optimal efficiency in onboarding sessions.
• Monitor and maintain quality standards, providing ongoing coaching, feedback, and guidance to team members to drive performance.
• Analyze key performance metrics (activation, adoption, conversion) to identify trends, uncover challenges, and implement improvements.
• Conduct onboarding calls on a limited basis, mainly for high-priority accounts or as needed to support the team.
• Collaborate with cross-functional teams, including Product, Support, and Business teams, to escalate issues and relay valuable customer feedback.
• Continuously refine onboarding processes based on data-driven insights, ensuring the team is maximizing conversion and customer success.
• Ensure consistency in messaging, methodology, and best practices, optimizing scripts, flows, and engagement strategies.
• Serve as the main escalation point for complex onboarding challenges, ensuring rapid resolution and customer satisfaction.
  
  

Requirements

• 10+ years of experience in customer-facing roles, with at least 4+ years leading a team in a Sales, Onboarding, or Customer Success environment—a must.
• Experience leading teams that perform video-calls with customers—highly preferred.
• Excellent business-level communication skills in English for seamless interaction with customers and internal teams.
• Proven ability to analyze performance data, identify insights, and drive continuous improvement in team results.
• Strong leadership, coaching, and motivational skills, ensuring the team remains high-performing and engaged.
• Highly process-driven, with the ability to analyze, develop, optimize and automate high-scale business processes and flows.
  
  

Guesty is proud to be an Equal Opportunity Employer. We provide equal employment opportunities to all employees and applicants regardless of race, color, religion, sex, age, national origin, disability, veteran status, pregnancy, sexual orientation, or any other characteristic protected by law.

About The Position

Guesty is the all-in-one platform for short-term rental hosts to automate and optimize every aspect of their property management operations. With purpose-built technology, industry-wide expertise, and an R&D team of 250+ engineers, Guesty ensures that hospitality businesses can streamline and achieve growth while delivering the best value to guests. With a complete suite of features and 150+ industry partners, including major booking OTAs like Airbnb, Vrbo, Booking.com, Tripadvisor, Expedia, Hopper, Google Travel, and many more, Guesty is transforming the hospitality industry with innovative solutions. Today, Guesty has 15 offices and 700+ team members across the globe.

Our Guesty Lite team is on the lookout for an exceptional Customer Onboarding Team Leader to join us. Are you ready to take on a new challenge and make an impact? We'd love to hear from you!

Responsibilities

• Manage and oversee a team of Customer Onboarding Specialists, ensuring seamless team operations and a high standard of customer experience.
• Own shift planning and workload allocation, ensuring full coverage and optimal efficiency in onboarding sessions.
• Monitor and maintain quality standards, providing ongoing coaching, feedback, and guidance to team members to drive performance.
• Analyze key performance metrics (activation, adoption, conversion) to identify trends, uncover challenges, and implement improvements.
• Conduct onboarding calls on a limited basis, mainly for high-priority accounts or as needed to support the team.
• Collaborate with cross-functional teams, including Product, Support, and Business teams, to escalate issues and relay valuable customer feedback.
• Continuously refine onboarding processes based on data-driven insights, ensuring the team is maximizing conversion and customer success.
• Ensure consistency in messaging, methodology, and best practices, optimizing scripts, flows, and engagement strategies.
• Serve as the main escalation point for complex onboarding challenges, ensuring rapid resolution and customer satisfaction.
  
  

Requirements

• 10+ years of experience in customer-facing roles, with at least 4+ years leading a team in a Sales, Onboarding, or Customer Success environment—a must.
• Experience leading teams that perform video-calls with customers—highly preferred.
• Excellent business-level communication skills in English for seamless interaction with customers and internal teams.
• Proven ability to analyze performance data, identify insights, and drive continuous improvement in team results.
• Strong leadership, coaching, and motivational skills, ensuring the team remains high-performing and engaged.
• Highly process-driven, with the ability to analyze, develop, optimize and automate high-scale business processes and flows.
  
  

Guesty is proud to be an Equal Opportunity Employer. We provide equal employment opportunities to all employees and applicants regardless of race, color, religion, sex, age, national origin, disability, veteran status, pregnancy, sexual orientation, or any other characteristic protected by law.