Mid-Market Onboarding Lead

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About the role

  • Mid-Market Onboarding Lead guiding Cloudbeds’ North American hotel customers from contract through go-live. Leading onboarding teams and improving implementation quality, retention, and customer satisfaction.

Responsibilities

  • Lead, coach, and develop the North America team of Onboarding Project Managers and Mid-Market Coaches
  • Run call reviews and kickoff preparation and coach customer-facing quality
  • Oversee strategic North American key accounts and multi-property groups through go-live and handoff
  • Own regional account intake and assignment based on complexity and capacity
  • Act as the first escalation point for at-risk North American onboardings
  • Ramp new hires through regional training, shadowing, and readiness certification
  • Track and improve time-to-live, deployment quality, onboarding CSAT, Hypercare outcomes, and early retention
  • Partner with Sales, Account Management, Hypercare, Support, Professional Services, Product, and third-party consultants
  • Help customers redesign workflows, reporting, and SOPs when switching from other PMS platforms
  • Handle team questions, case investigations, and call coverage
  • Use AI and automation to reduce administrative work

Requirements

  • 5+ years in hotel operations or hospitality technology; experience limited to OTAs, GDS, or travel distribution does not meet this requirement
  • 2+ years directly managing customer-facing team members in onboarding, implementation, professional services, or customer success, including hiring, coaching, and performance management
  • Hands-on experience leading multi-property or 40+ room full-service hotel PMS implementations, from kickoff through go-live
  • Strong understanding of North American hotel operations: front office, reservations, distribution, revenue management, payments, and reporting
  • Consultative, hospitality-first communication style with executives and front-line staff
  • Project-management discipline: scope, milestones, risks, and stakeholder communication across many concurrent projects
  • Comfortable with dashboards and Salesforce or a similar CRM; willing to adopt AI tools
  • Calm, organized, and decisive in a fast-growing, remote-first environment
  • Currently authorized to work in the location where the position is located without requiring visa sponsorship
  • Optional: experience with Oracle Opera; Spanish fluency; PMP or similar project-management certification; experience with hotel management companies, hotel consultants, or reseller partners; familiarity with revenue management systems, guest experience tools, or hospitality payments

Benefits

  • 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

Job type

Full Time

Experience level

Senior

Salary

Not specified

Degree requirement

No Education Requirement

Tech skills

OraclePMPSwitching

Location requirements

RemoteCanada

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