SMB Onboarding Lead

How You'll Make an Impact:

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 Customer Onboarding Team:

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.

What You Bring to the Team:

• 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.

What Sets You Up for Success:

• 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.

Recommended Skills to Stand Out:

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.

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