About this role.
This role leads the onboarding function for Cloudbeds' mid-market segment, responsible for guiding customers from contract signature through go-live and adoption. The Director will build standardized frameworks, metrics, and team capabilities to deliver a world-class onboarding experience at scale. They will manage a team of project managers and coaches, ensuring onboarding velocity, quality, and customer satisfaction. The position requires strong leadership, cross-functional collaboration with Sales, Product, and Account Management, and a data-driven approach to improve processes. This is an opportunity to shape a critical customer journey in a fast-growing hospitality tech company.
Role DNA
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Job Complexity
4/5Pace & Pressure
5/5Autonomy Level
5/5Communication Load
5/5Salary analysis
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Core skills
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Cover letter sample
I am excited to apply for the Global Director, Mid-Market Onboarding position at Cloudbeds. With extensive experience in hospitality technology and a passion for customer success, I am confident I can drive the onboarding function to new heights.
In my previous role, I led a team responsible for onboarding complex enterprise clients, implementing standardized frameworks that improved deployment velocity by 30% and increased customer satisfaction scores. I am adept at building metrics-driven cultures and collaborating cross-functionally to align sales, product, and account management.
I thrive in fast-paced, high-growth environments and enjoy solving complex problems while developing team capabilities. I look forward to contributing to Cloudbeds' mission of transforming hospitality through exceptional onboarding experiences.
Sample interview questions
I led a team of 12 onboarding managers at a hospitality tech company. We measured success through time-to-go-live, customer satisfaction (CSAT) at 30 days post-go-live, and early-stage churn rates. I implemented regular portfolio reviews to identify at-risk projects and improve processes.
I would start by analyzing our most successful deployments to identify common patterns. Then, I'd create modular playbooks that can be customized for property size, complexity, and integrations. I would involve the team in iterative testing and gather feedback from customers and account management to refine the framework.
In one instance, sales had overpromised on customization, causing scope creep. I facilitated a meeting with sales, product, and the customer to reset expectations, prioritizing must-haves over nice-to-haves. We created a phased plan that delivered core value quickly and followed up with additional features, maintaining customer trust.
I believe in setting clear performance standards and providing regular feedback. I conduct weekly one-on-ones, focusing on both skill development and career growth. I also encourage a test-and-learn culture, where team members can experiment with new approaches and share learnings. Additionally, I provide opportunities for them to lead cross-functional initiatives.
I use historical data on onboarding duration, team utilization, and future sales forecasts to model capacity needs. I factor in ramp-up time for new hires and seasonality. I partner with finance and sales to align on headcount decisions, and I build flexibility into the plan to adjust for changes in demand.
What Makes Us Unique
At Cloudbeds, we’re not just building software, we’re transforming hospitality. Our intelligently designed platform powers properties across 150 countries, processing billions in bookings annually. From independent properties to 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 become the World’s Best Hotel PMS Solutions Provider and landed on Deloitte’s Technology Fast 500 again in 2024 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
Compensation: Depending on your skills and experience, you can expect your annual compensation to be between $180,000 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).
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What to Expect – Your Journey with Us
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. 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
Company Awards to Check Out!
- 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)
Discover our Benefits:
- Remote First, Remote Always
- PTO in accordance with local labor requirements
- Monthly Wellness Fridays – enjoy an extra long weekend every month
- Full 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 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 accommodations@cloudbeds.com. 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.
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