SMB Onboarding Lead

As a leader within the Customer Onboarding Team, you will cultivate a highly effective, close-knit, and collaborative team that consistently delivers exceptional support. By ensuring seamless and successful onboarding experiences, your leadership directly translates into immediate value realization and long-term retention for our customers.

In this role, you will champion our AI Smarts + Hospitality Hearts mission, guiding your team to move from a pure training function to a strategic business partnership. You will lead a group of Caring Rebels who model Hospitality Before Efficiency, empowering clients to use our platform to deliver an experience of Unreasonable Hospitality. If you are driven by emotional intelligence, trust-building, and are ready to make a significant impact by guiding, mentoring, and setting the standard for a deeply personalized customer journey, we look forward to having you lead the way!

Our Onboarding team is where Hospitality Hearts meet Smart Solutions. We are a fully remote group of former hoteliers and customer experience professionals, focused on removing unnecessary manual work so we can spend more time on our "human magic": building and strengthening relationships, and ensuring our customers feel confident and supported from day one. If you are driven by emotional intelligence, trust-building, and delivering deeply personalized hospitality moments instead of repetitive operational tasks, you and your team will feel right at home here.

• Embody the Caring Rebel Mindset: Cultivate, mentor, motivate, and empower a world-class team of Onboarding Coaches to care for our customers and their properties just as they would for a guest in a hotel.
• Standardize the Repeatable, Personalize the Meaningful: Drive the adoption of AI and modern tooling across your team to eliminate administrative drag, freeing them up to focus on strategic onboarding guidance, deep product adoption, and human magic.
• Lead Performance & Growth: Own the preparation, execution, and follow-up for 1-on-1s, check-ins, and performance reviews. Identify, communicate, and facilitate learning and career-growth opportunities for each member of your team.
• Strategic Portfolio Management: Monitor a segment of Cloudbeds customers with associated retention goals, analyzing utilization and customer data independently to discover insights and improve the onboarding experience.
• Escalation & Advocacy: Serve as a confident, knowledgeable, and patient escalation point for complex technical or operational inquiries from clients, third-party stakeholders, and key decision-makers.
• Cross-Functional Collaboration: Partner with Sales, Product, and Support to convert onboarding feedback into systemic operational improvements, shortening delivery timeframes and ensuring Cloudbeds' value is realized early.
• Thought Leadership: Provide leadership in hospitality training, ensuring full client context is maintained throughout the journey, and that all new knowledge is captured, searchable, and reusable.
• Commercial Mindset: Partner with Sales to define success, demonstrate ROI, drive customer retention, promote product value, and identify upsell opportunities.
• Data-Driven Success: Design, implement, and track quantitative and qualitative metrics to measure the success of projects, people, and processes, including driving best practices around customer outreach for reviews.

• Show Strong AI Smarts: Exceptional technical aptitude and learning agility. You work seamlessly with AI, pick up new software quickly, and feel comfortable adapting to evolving technology to unlock more time for personalized relationships.
• Demonstrate Your Hospitality Heart: Over 2 years of direct leadership experience within a hospitality property (e.g., Front Desk Manager, Revenue Manager, Concierge) or at least 3 years of relevant Hospitality SaaS industry experience in a customer-facing leadership/matrix role. (Prior experience as a Senior or Key Account Onboarding Coach within Cloudbeds is a major plus).
• Empathy & Relationship Champion: High emotional intelligence with a proven ability to build trust, resolve competing priorities under pressure, and create relationships across all levels of an organization (internally and externally).
• Agile Leadership: Ability to manage people, processes, and accounts effectively in an agile system and matrix reporting environment, while overseeing comprehensive learning and development plans for your team.
• Clear Communicator: Ability to clearly, concisely, and confidently synthesize technical and business concepts in both written and verbal contexts.
• Operational Excellence: Highly accountable, data-driven, and detail-oriented with background experience in modern operating systems (CRMs like Salesforce, OTAs, PMS backgrounds, etc.).
• Inclusive Outlook: Comfortable leading and working alongside people from diverse cultures and backgrounds.

1. Fluency or working knowledge of Spanish, Portuguese, English, Thai, or Tagalog.
2. Project Management or Change Management certification (e.g., PMP, Agile, Prosci).
3. Hospitality degree preferred.

• Best All-In-One Hotel Management System | HotelTechAwards (2025)
• Overall 10 Best Places to Work | HotelTechAwards (2025)
• Most Loved Workplace® Certified (2024)
• Top 10 People’s Choice (2024)
• Deloitte Technology Fast 500 (2024)

Cloudbeds is proud to be an Equal Opportunity Employer that celebrates the diversity in our global team! We do not discriminate based upon race, religion, color, national origin, gender (including pregnancy, childbirth, or related medical conditions), sexual orientation, gender identity, gender expression, age, status as a protected veteran, status as an individual with a disability, or other applicable legally protected characteristics.

Cloudbeds is committed to the full inclusion of all qualified individuals. As part of this commitment, Cloudbeds will ensure that persons with disabilities are provided reasonable accommodations in the hiring process. We encourage deaf, hard-of-hearing, deaf-blind, and deaf-disabled individuals to apply. If reasonable accommodation is needed to participate in the job application or interview process or to perform essential job functions, please contact our HR team by phone at (858) 201-7832 or via email at accommodations@cloudbeds.com. Cloudbeds will provide an American Sign Language (ASL) interpreter where needed as a reasonable accommodation for the hiring processes.

To all Staffing and Recruiting Agencies: Our Careers Site is only for individuals seeking a job at Cloudbeds. Staffing, recruiting agencies, and individuals being represented by an agency are not authorized to use this site or to submit applications, and any such submissions will be considered unsolicited. Cloudbeds does not accept unsolicited resumes or applications from agencies. Please do not forward resumes to our jobs alias, Cloudbeds employees, or any other company location. Cloudbeds is not responsible for any fees related to unsolicited resumes/applications.

#LI-REMOTE