Global Director, Mid-Market Onboarding

About the Position

Global Director, Mid-Market Onboarding

Canada; Europe; North America

At Cloudbeds, we're transforming hospitality with our intelligently designed platform that powers properties across 150 countries, processing billions in bookings annually. As the 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.

Responsibilities

• 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

Requirements

• 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

Nice to Have

• 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

Compensation

Depending on your skills and experience, you can expect your annual compensation to be between $160,000 and $190,000 USD. Please note that we maintain high flexibility, and packages above this range will be considered. (The salary is only for US-based candidates).

We Offer

• Remote First, Remote Always
• PTO in accordance with local labor requirements
• Monthly Wellness Fridays - enjoy an extra-long weekend every month
• 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

About the Company

Behind Cloudbeds' revolutionary technology is a team of redefining what's possible in hospitality. We're 650+ employees across 40+ countries, bringing together elite engineers, AI architects, world-class designers, 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.

Learn more online at cloudbeds.com

Company Awards:

• 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)

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 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 [email protected]. 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