Global Director, Mid-Market Onboarding

Cloudbeds; Chicago (IL); Remote; USD 140,000 - 200,000; Full time

Benefits offered by this job

Remote First

PTO

Parental Leave

Home office stipend

Cloudbeds University

Professional development

Job summary

Cloudbeds is seeking a Senior Onboarding Lead to guide the Mid-Market Onboarding team and own end-to-end onboarding outcomes for diverse hotel clients. This role focuses on building scalable onboarding frameworks, improving deployment velocity, and driving high customer satisfaction in a globally distributed, remote-first environment.

You will collaborate across Sales, Product, Support, and Account Management, with a strong emphasis on data-driven decisions, KPIs, and cross-functional leadership

Qualifications

• 7+ years in hospitality or hospitality tech with onboarding or implementation leadership.
• Proven experience leading distributed teams across time zones.
• Strong project management with scope, milestones, timelines and risk mitigation.
• Data-driven with KPI dashboards and insights to drive decisions.
• Exceptional communication and customer advocacy in complex deployments.
• Ability to design frameworks and roll them out in scale-up environments.
• Experience with PMS, payments, or hospitality fintech is a plus.

Responsibilities

• Lead, coach, and develop the Mid-Market Onboarding team including onboarding managers.
• Own end-to-end onboarding outcomes from sales handoff to go-live and adoption.
• Build standardized onboarding frameworks and configuration standards for multi-property deployments.
• Establish metrics: onboarding velocity, quality scores, CSAT/NPS, and early-lifecycle retention.
• Own capacity planning and staffing in coordination with leadership.
• Serve as escalation point for complex or at-risk deployments.
• Collaborate cross-functionally with Sales, Product, Support, and Account Management.
• Identify and fix gaps in training quality, error detection, and deployment velocity.

Skills

Team leadership

Onboarding

Project management

Hospitality tech

Cross-functional collaboration

Data-driven decision making

Spanish/Portuguese

Job description

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.

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 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.

• 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
• 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
• 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.

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.

• 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)
• 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

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 [phone] or via email at [e-mail]. Cloudbeds will provide an American Sign Language (ASL) interpreter where needed as a reasonable accommodation for the hiring process.