Vice President of Customer Success

Department: Customer Success
Reports To: Chief Operating Officer (COO)
Location: Remote (with periodic travel as needed)

Wander is reinventing the vacation rental experience by combining world-class properties, technology-driven management, and a seamless customer experience. We specialize in managing luxury vacation rentals while delivering unmatched guest experiences and maximizing owner and property manager success. Our mission is to create joyful travel experiences through innovation, transparency, and exceptional service.

The Vice President (VP) of Customer Success will lead Wander’s Customer Success business unit. This role is responsible for driving long-term satisfaction and success for both property managers and Wander-operated property owners by leading two core teams:

1. Customer Success – Property Managers: focused on supporting SaaS B2B clients using Wander Sites, our property management system and booking engine.
   

2. Customer Success – Operated: focused on supporting operated property owners with communications, transparency, and performance insights.
   

The VP will set the strategic vision for Customer Success, establish scalable processes, and lead a growing team of managers and representatives. This leader will be accountable for client satisfaction, operational excellence, and cross-department collaboration to ensure Wander delivers a world-class experience to property managers and owners alike.

• Leadership & Strategy

  • Define the vision and strategy for Wander’s Customer Success business unit.

  • Lead, mentor, and grow a team of managers and representatives across two groups (Property Managers & Operated).

  • Establish clear KPIs and performance metrics for client satisfaction, retention, and support efficiency.
    

• Customer Success – Property Managers (Wander Sites)

  • Oversee product onboarding, training, and ongoing support for SaaS B2B clients.

  • Ensure strong adoption and satisfaction with Wander Sites.

  • Act as executive sponsor for key property management groups, building trust and long-term partnerships.
    

• Customer Success – Operated

  • Maintain exceptional communication and transparency with operated property owners.

  • Oversee financial and performance reporting, ensuring clarity and accuracy.

  • Proactively identify opportunities to improve owner satisfaction and property performance.
    

• Operational Excellence

  • Implement processes for efficient triage and escalation of issues through the Wander OS Owner Chat.

  • Drive monthly reporting on client satisfaction, issue resolution, and retention trends.

  • Establish feedback loops with Product, Operations, and Marketing teams to continuously improve services.
    

• Cross-Functional Collaboration

  • Partner with Product to improve Wander Sites based on client feedback.

  • Collaborate with Operations to ensure smooth property performance.

  • Work with Marketing to align messaging and support client success stories.
    

• 10+ years of experience in Customer Success, customer success, or account management, with at least 5 years in a senior leadership role.

• Proven success leading SaaS B2B customer success teams and/or hospitality/property management Customer Success.

• Strong understanding of SaaS onboarding, adoption, and escalation management.

• Experience managing both enterprise-level clients and high-net-worth property owners preferred.

• Demonstrated ability to define and execute strategic plans while driving measurable results.

• Strong financial and operational acumen, with the ability to explain performance metrics clearly.

• Excellent communication, relationship-building, and conflict resolution skills.

• Strategic leadership and team development.

• Customer success and Customer Success expertise.

• SaaS product knowledge and technical aptitude.

• Strong problem-solving and decision-making.

• Excellent written and verbal communication.

• Ability to operate in a fast-paced, high-growth environment.
  

• Competitive salary and performance-based incentives.

• Health, dental, and vision insurance.

• Flexible PTO and remote-friendly culture.

• Opportunity to travel to Wander properties and experience the brand firsthand.

• Be part of a mission-driven company transforming the future of vacation rentals.