Mid-Market Onboarding Lead

Cloudbeds

. Lead, coach, and develop the North America team of Onboarding Project Managers and Mid-Market Coaches .

Posted 11/3/2026full-timeRemote • CanadaSeniorWebsite

Core Competencies

Role fit

Core Competencies

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Demonstrates expertise in leading and developing customer-facing teams within the hospitality technology sector, with a strong focus on onboarding project management and operational excellence. Proficient in managing multi-property hotel PMS implementations and enhancing customer satisfaction through effective communication and project management.

Highest-signal resume keywords

Hotel Operations ManagementOnboarding Project ManagementCustomer Success LeadershipPMS Implementation ExperienceSalesforce CRM Proficiency

ATS Keywords

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Applicant Tracking System Keywords

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Hard Skills

OnboardingProject ManagementPMS ImplementationWorkflow RedesignPerformance ManagementData AnalysisCustomer Satisfaction TrackingAI Tools AdoptionRevenue ManagementReporting

Soft Skills

CoachingCommunicationOrganizational SkillsDecisivenessConsultative Approach

Tools & Technologies

SalesforceOracle OperaDashboardsAI Automation ToolsGuest Experience Tools

Certifications & Qualifications

PMP Certification

Industry Keywords

Hospitality TechnologyNorth American Hotel OperationsMulti-Property ManagementTravel DistributionCustomer-Facing Teams

Tech Stack

Tools & technologies

OraclePMPSwitching

About the role

Key responsibilities & impact

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

What you’ll need

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

Comp & perks

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