[Hiring] Global Director, Mid-Market Onboarding @Canada Job Posts

Role Description

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

• Passionate about delivering exceptional customer experiences.
• Encourages innovation, collaboration, and continuous improvement.
• Values and empowers every team member to share feedback, ideas, and insights.
• Proactive communicators, collaborative problem-solvers, and true customer advocates.

What You Bring to the Team

• Lead, coach, and develop the Mid-Market Onboarding team.
• Own end-to-end onboarding outcomes for mid-market customers.
• Build standardized onboarding frameworks, SOPs, and configuration standards.
• Establish and own the metrics that matter.
• Own capacity and staffing planning for the division.
• Serve as a senior escalation point for complex or at-risk mid-market deployments.
• Partner cross-functionally with Sales, Product, Support, Professional Services, and Account Management.

Qualifications

• 7+ years in hospitality or hospitality technology, including hands-on customer onboarding or implementation experience and team leadership.
• Track record of building or significantly improving onboarding and implementation functions and frameworks.
• Proven people-leadership experience in a distributed, global environment.
• Strong project-management foundation 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.
• 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.

Requirements

• Applicants must be currently authorized to work in the location where the position is located without requiring visa sponsorship.

Benefits

• Remote work flexibility in eligible locations across Canada.
• Open PTO beyond statutory minimums, paid Canadian holidays, and 5 paid sick days.
• Cloudbeds matches 100% of your contributions, up to 4% of eligible earnings.
• Extended healthcare coverage, including prescription drugs, dental, vision, and paramedical services.
• Company-paid Life & AD&D insurance (3x annual earnings, up to $500,000).
• Paid maternity and partner leave, plus confidential 24/7 Employee Assistance Program (EAP) support.
• A one-time home office setup stipend and recurring WiFi and phone stipends.
• Professional development through Cloudbeds University and 1 paid Volunteer Day per quarter.

Company Description

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, sexual orientation, gender identity, 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.