Global Director, Mid-Market Onboarding

What Makes Cloudbeds Unique

At Cloudbeds , we're not just building software, we’re transforming hospitality. Our platform powers hotels across 150 countries, processing billions in bookings annually. From boutique properties to large hotel groups, we help hoteliers transform operations and uplevel their commercial strategy through a unified platform that integrates with hundreds of partners. And we do it with a completely remote team. Imagine working alongside global innovators to build AI-powered solutions that solve hoteliers' biggest challenges. Since our founding in 2012, we've continually been recognized for excellence, most recently earning top honors at the 2026 HotelTechAwards for Best Hotel Management Software and landing on Deloitte's Technology Fast 500 again, but we're just getting started.

How You'll Make an Impact:

As Global Director, Mid-Market Onboarding, you will own and scale the onboarding function for Cloudbeds' fastest-growing and most complex customer segment. You'll lead the team responsible for guiding mid-market customers from contract signature through go-live, adoption, and a clean transition to Account Management. You'll build the frameworks, standards, metrics, and team capability that make that experience world-class and repeatable at scale.

You'll inherit a team of dedicated ICs and leads that have been experimenting with new ways to support these customers and improve their experience. Your charter is to get leadership in place and be maniacal about customer experience while building the project-management rigor that complex mid-market deployments demand. You'll be measured on onboarding velocity, deployment quality, customer satisfaction, and the long-term retention impact of a strong start.

Our Onboarding Team:

Our team is passionate about delivering exceptional customer experiences and helping hoteliers succeed with Cloudbeds from day one. We build together with a test-and-learn mindset that encourages innovation, collaboration, and continuous improvement. Every team member is valued and empowered to share feedback, ideas, and insights so we can learn, grow, and improve both as individuals and as a team. Leaders who thrive here are proactive communicators, collaborative problem-solvers, and true customer advocates who enjoy navigating complexity while building the systems and people that scale it.

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, growth paths, and 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 — diagnosing and fixing execution gaps in training quality, error detection, and deployment velocity

Build standardized onboarding frameworks, SOPs, and configuration standards for complex multi-property and 25–100+ room deployments that balance customization with scalability

Establish and own the metrics that matter: onboarding velocity, deployment quality scores, training completion, CSAT/NPS, and early-lifecycle retention — monitoring portfolio health and intervening early on at-risk projects

Own capacity and staffing planning for the division — forecasting demand, balancing workload across the team, and partnering with leadership on headcount decisions

Serve as a senior escalation point for complex or at-risk mid-market deployments and partner with Account Management on clean, trust-preserving handoffs

Partner cross-functionally with Sales, Product, Support, Professional Services, and Account Management — bridging what gets sold and what gets delivered, and contributing to the broader strategy for how Cloudbeds serves mid-market and enterprise-adjacent customers

What Sets You Up for Success:

7+ years in hospitality or hospitality technology, including hands-on customer onboarding or implementation experience and team leadership (time at a hotel, hotel group, or a PMS or hospitality-tech company; OTA or travel-distribution experience on its own does not count)

Track record of building or significantly improving onboarding and implementation functions and frameworks

Proven people-leadership experience — hiring, coaching, and developing customer-facing teams in a distributed, global environment

Strong project-management foundation: scope, milestones, timelines, and risk mitigation applied to complex multi-stakeholder deployments

Deep understanding of hotel operations and the complexity of serving multi-property, mid-market hospitality customers

Ability to move fluidly between strategy and execution — you can design the framework and roll up your sleeves to implement it

Data-driven: comfortable with KPIs, dashboards, and using insights to drive decisions

Bonus Skills to Stand Out:

Additional language fluency (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

Work Authorization: Please note that applicants must be currently authorized to work in the location where the position is located without requiring visa sponsorship. At this time, Cloudbeds is unable to provide sponsorship for work visas.

#LI-SD1

Work Authorization: Please note that applicants must be currently authorized to work in the location where the position is located without requiring visa sponsorship. At this time, Cloudbeds is unable to provide sponsorship for work visas .

• What to Expect - Your Journey with Us
• Behind Cloudbeds' revolutionary technology is a team redefining what's possible in hospitality. We're 650+ team members across 40+ countries, bringing together elite engineers, AI architects, world-class designers, hoteliers, and hospitality veterans to solve challenges others haven't dared to tackle. Our diverse team speaks 30+ languages, but we all share one language: a passion for innovation and travel. From pioneering breakthroughs in machine learning to revolutionizing how hotels operate, we're not just watching the future of hospitality unfold – we're coding it, designing it, writing it, and shipping it. If you're ready to work alongside some of the brightest minds in tech who are obsessed with using AI to transform a trillion-dollar industry, this is your chance to be part of something extraordinary.

Learn more online at cloudbeds.com

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)

Discover our 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

Everyone is Welcome - A Culture of Inclusion

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 charact