Global Director, Mid-Market Onboarding

Canada Job Posts; Canada; Remote; CAD 130,000 - 190,000; Full time

Benefits offered by this job

Remote work across Canada

Open PTO

Matching retirement contributions

Health & Dental coverage

Life & Disability insurance

Family leave & mental health support

Home office stipend

Growth & Community

Job summary

Cloudbeds is seeking a Global Director of Mid-Market Onboarding to own and scale onboarding for our fastest-growing customer segment. You will lead a distributed team responsible for guiding mid-market customers from contract to go-live, adoption, and transition to Account Management, building world-class onboarding frameworks and processes.

You will measure onboarding velocity, deployment quality, and customer satisfaction while driving long-term retention and scalable operations across a

Qualifications

• 7+ years in hospitality or hospitality tech, with hands-on onboarding or implementation and team leadership.
• Track record of building or improving onboarding/implementation functions and frameworks.
• Proven people-leadership in a distributed, global environment.
• Strong project-management, scope, milestones, timelines, risk mitigation.

Responsibilities

• Lead and develop the Mid-Market Onboarding team, setting expectations, standards, growth paths, and accountability.
• Own end-to-end onboarding outcomes from sales handoff to go-live, adoption, and transition to Account Management.
• Build standardized onboarding frameworks, SOPs, and configuration standards for multi-property deployments.
• Establish and own metrics: onboarding velocity, deployment quality, training completion, CSAT/NPS, retention.

Skills

Onboarding leadership

Hospitality tech

Project management

KPIs & dashboards

Cross-functional collaboration

Team leadership

Customer experience

Tools

PMS systems

CRM tools

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.

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.

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.

• 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)

Discover Our Canada Benefits

• #RemoteFirst: Work from home in eligible locations across Canada, with flexibility to work and travel in accordance with company policies.
• Time Off & Wellness: Open PTO beyond statutory minimums, paid Canadian holidays, and 5 paid sick days.
• Retirement Savings: Cloudbeds matches 100% of your contributions, up to 4% of eligible earnings.
• Health, Dental & Vision: Extended healthcare coverage, including prescription drugs, dental, vision, and paramedical services for you and your eligible dependents.
• Life & Disability Protection: Company-paid Life & AD&D insurance (3x annual earnings, up to $500,000), with disability and critical illness coverage also available.
• Family & Mental Health: Paid maternity and partner leave, plus confidential 24/7 Employee Assistance Program (EAP) support.
• Home Office Support: A one-time home office setup stipend and recurring WiFi and phone stipends.
• Growth & Community: Professional development through Cloudbeds University and 1 paid Volunteer Day per quarter through Cloudbeds Cares.

Benefits are subject to eligibility requirements and plan terms.

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 [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.

Equal Employment Opportunity Information

For government reporting purposes, we ask candidates to respond to the below self-identification survey. Completion of the form is entirely voluntary. Whatever your decision, it will not be considered in the hiring process or thereafter. Any information that you do provide will be recorded and maintained in a confidential file. We do not discriminate on the basis of any protected group status under any applicable law. I f you choose to complete this survey, your responses may be used to identify areas of improvement in our hiring process.

How would you describe your gender identity? * Select...

How would you describe your racial/ethnic background? * Select...

Do you have a disability or chronic condition (physical, visual, auditory, cognitive, mental, emotional, or other) that limits one or more of your major life activities, including mobility, communication (seeing, hearing, speaking), and learning? * Select...