Mid-Market Onboarding Lead

C
CloudbedsHospitality software
Work from home in eligible locations across CanadaFull-TimeLead
Salary not disclosed
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Job Details

Experience
5+ years in hotel operations or hospitality technology; 2+ years directly managing customer-facing team members in onboarding, implementation, professional services, or customer success
Required Skills
Project ManagementSalesforceTeam management

Requirements

  • Have 5+ years of experience in hotel operations or hospitality technology; experience limited to OTAs, GDS, or travel distribution does not meet this requirement.
  • Have 2+ years directly managing customer-facing team members in onboarding, implementation, professional services, or customer success, including hiring, coaching, and performance management.
  • Have hands-on experience leading multi-property or 40+ room full-service hotel PMS implementations from kickoff through go-live.
  • Understand North American hotel operations, including front office, reservations, distribution, revenue management, payments, and reporting.
  • Bring a consultative communication style for working with executives and front-line staff, including delivering difficult news and resetting expectations.
  • Apply project-management discipline to scope, milestones, risks, and stakeholder communication across concurrent projects.
  • Be comfortable using dashboards and Salesforce or a similar CRM.
  • Be ready to adopt AI tools and work in a fast-growing, remote-first environment with shifting priorities.
  • Oracle Opera implementation or operations experience is a bonus.
  • Spanish fluency at a business-professional level is a bonus.
  • PMP or a similar project-management certification is a bonus.
  • Experience with hotel management companies, hotel consultants, or reseller partners is a bonus.
  • Familiarity with revenue management systems, guest experience tools, or hospitality payments is a bonus.

Responsibilities

  • Lead, coach, and develop the North America team of Onboarding Project Managers and Mid-Market Coaches.
  • Review call quality and kickoff preparation, and coach the team on customer-facing conversations.
  • Oversee a small portfolio of strategic North American accounts through go-live and handoff.
  • Review account requests and assign accounts based on complexity and team capacity.
  • Act as the first escalation point for at-risk onboardings and reset plans with customers.
  • Train and shadow new hires, certify readiness for live accounts, and help shape hiring profiles.
  • Track and improve time-to-live, deployment quality, onboarding CSAT, Hypercare outcomes, and early retention using Salesforce dashboards and onboarding tools.
  • Partner with Sales, Account Management, Hypercare, Support, Professional Services, and Product on handoffs and recurring issues.
  • Help customers switching from other PMS platforms redesign workflows, reporting, and SOPs.
  • Coordinate with third-party consultants and partners supporting implementations.
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