Global Director, Mid-Market Onboarding - Cloudbeds

About Cloudbeds

Cloudbeds is transforming the hospitality industry by providing a comprehensive platform that powers hotels in over 150 countries. We integrate with hundreds of partners to help hoteliers streamline operations and enhance their commercial strategies. As a completely remote team, we foster innovation and build AI-powered solutions to address the biggest challenges faced by hoteliers.

Your Impact

As the Global Director, Mid-Market Onboarding, you will be responsible for scaling and optimizing the onboarding process for Cloudbeds' fastest-growing customer segment. You will lead a team dedicated to guiding mid-market clients from contract signing through successful go-live, adoption, and a smooth transition to Account Management. Your role involves developing robust frameworks, standards, metrics, and team capabilities to ensure a world-class and repeatable onboarding experience.

You will inherit a team that is actively experimenting with new support methods. Your primary focus will be on establishing strong leadership, prioritizing customer experience, and implementing the project management rigor required for complex mid-market deployments. Success will be measured by onboarding velocity, deployment quality, customer satisfaction, and the long-term retention impact of a positive initial experience.

Our Onboarding Team Culture

Our onboarding team is driven by a passion for delivering exceptional customer experiences and empowering hoteliers to succeed with Cloudbeds. We embrace a test-and-learn mindset, encouraging innovation, collaboration, and continuous improvement. Every team member's feedback and insights are valued, contributing to individual and team growth. Leaders who thrive here are proactive communicators, collaborative problem-solvers, and dedicated customer advocates who excel at navigating complexity and building scalable systems and teams.

What You Bring to the Team

• Lead, coach, and develop the Mid-Market Onboarding team, including Onboarding Project Managers and senior coaches, setting clear expectations, performance standards, and fostering a culture of accountability and continuous improvement.
• Own end-to-end onboarding outcomes for mid-market customers, from sales handoff through go-live, adoption, and transition to Account Management, identifying and resolving execution gaps in training quality, error detection, and deployment velocity.
• Develop standardized onboarding frameworks, SOPs, and configuration standards for complex multi-property and 25–100+ room deployments, balancing customization with scalability.
• Establish and own key metrics: onboarding velocity, deployment quality scores, training completion, CSAT/NPS, and early-lifecycle retention, monitoring portfolio health and intervening proactively on at-risk projects.
• Manage capacity and staffing planning for the division, forecasting demand, balancing workload, and partnering with leadership on headcount decisions.
• Serve as a senior escalation point for complex or at-risk mid-market deployments and collaborate with Account Management on seamless, trust-building handoffs.
• Partner cross-functionally with Sales, Product, Support, Professional Services, and Account Management to bridge the gap between sales promises and delivery, contributing to the broader strategy for serving mid-market and enterprise-adjacent customers.

What Sets You Up for Success

• 7+ years in hospitality or hospitality technology, with hands-on customer onboarding or implementation experience and team leadership (experience at a hotel, hotel group, or a PMS/hospitality-tech company; OTA or travel-distribution experience alone is not sufficient).
• Proven track record of building or significantly improving onboarding and implementation functions and frameworks.
• Demonstrated people-leadership experience, including hiring, coaching, and developing customer-facing teams in a distributed, global environment.
• Strong project-management foundation, including scope, milestones, timelines, and risk mitigation for complex multi-stakeholder deployments.
• Deep understanding of hotel operations and the complexities of serving multi-property, mid-market hospitality customers.
• Ability to transition fluidly between strategy and execution, designing frameworks and actively participating in their implementation.
• Data-driven approach, comfortable with KPIs, dashboards, and using insights to inform decision-making.

Bonus Skills to Stand Out

• Fluency in additional languages (Spanish, Portuguese) at a business-professional level.
• Direct experience onboarding or implementing customers at a hospitality SaaS or PMS company.
• Familiarity with property management systems, payments, or hospitality fintech.
• Experience building onboarding or implementation functions at a scale-up stage company.
• Background working with hotel management companies, small chains, or the consultant ecosystem.

Compensation

Annual compensation is expected to be between $160,000 and $190,000 USD, depending on skills and experience. Packages above this range will be considered. (This salary range is for US-based candidates).

Work Authorization

Applicants must be currently authorized to work in their location without requiring visa sponsorship. Cloudbeds is unable to provide sponsorship for work visas at this time.

About Cloudbeds

Cloudbeds is a global team of 650+ members across 40+ countries, united by a passion for innovation and travel. We bring together elite engineers, AI architects, designers, hoteliers, and hospitality veterans to solve complex challenges. Our diverse team speaks over 30 languages and is dedicated to coding, designing, and shipping the future of hospitality, leveraging AI to transform a trillion-dollar industry.

Cloudbeds Awards

• Winner – Hotel Management Software | HotelTechAwards (2026)
• Overall 10 Best Places to Work | HotelTechAwards (2026)
• Overall Top 10 Hotelier's Choice | HotelTechAwards (2026)
• Finalist – Property Management Systems (PMS) & Channel Managers | HotelTechAwards (2026)
• Most Loved Workplace® Certified (2024)
• Deloitte Technology Fast 500 (2024)

Benefits

• Remote First, Remote Always
• PTO in accordance with local labor requirements
• Fully Paid Parental Leave
• Home office stipend based on country of residency
• Professional development courses in Cloudbeds University
• Access to professional development, including manager training, upskilling, and knowledge transfer.

Inclusion at Cloudbeds

Cloudbeds is an Equal Opportunity Employer committed to diversity and inclusion. We do not discriminate based on race, religion, color, national origin, gender, sexual orientation, gender identity, age, veteran status, disability, or any other protected characteristic. We provide reasonable accommodations for individuals with disabilities in the hiring process. If accommodation is needed, please contact our HR team at (858) 201-7832 or accommodations@cloudbeds.com. We will provide ASL interpreters as a reasonable accommodation when needed.

Note to Staffing and Recruiting Agencies: Our Careers Site is for individuals seeking employment at Cloudbeds. Unsolicited submissions from agencies are not accepted and will be considered unsolicited. Cloudbeds is not responsible for any fees related to unsolicited resumes or applications.