Remote Mid-Market Onboarding Lead - NA

Cloudbeds; Charlotte (NC); Remote; USD 100,000 - 140,000; Full time

Benefits offered by this job

Remote-first culture

PTO

Parental leave

Home office stipend

Professional development

Job summary

Cloudbeds seeks a Mid-Market Onboarding Lead for North America to own the onboarding experience for independent hotels, resorts, and multi-property groups moving to Cloudbeds. You will lead the regional team and oversee a small set of strategic NA accounts through go-live and handoff.

This remote-first, player-coach role requires strong hospitality operations knowledge, consultative communication, and a track record of driving successful multi-property PMS implementations.

Qualifications

• 5+ years in hotel operations or hospitality technology.
• 2+ years directly managing customer-facing team members in onboarding, implementation, or customer success.
• Hands-on experience leading multi-property PMS implementations from kickoff to go-live.
• Strong understanding of North American hotel operations: front office, reservations, distribution, revenue management, payments, reporting.
• A consultative, hospitality-first communication style with executives and frontline staff.
• Project-management discipline: scope, milestones, risks, and stakeholder communication.
• Comfortable with data and tooling: dashboards and Salesforce; AI tools are a plus.
• Experience implementing or operating enterprise systems such as Oracle Opera.

Responsibilities

• Lead, coach, and develop the North America onboarding team with clear expectations and growth paths.
• Oversee key accounts, ensuring go-live success and smooth handoffs to Account Management.
• Own regional intake and assignment of accounts based on complexity and capacity.
• Diagnose at-risk onboardings, reset plans, and decide on escalation or involvement of other services.
• Ramp new hires through regional training and readiness certification.
• Track regional performance using dashboards and Salesforce to spot risks early.
• Collaborate with Sales, Hypercare, Support, PS, and Product to close gaps.
• Translate client workflows from legacy PMS into Cloudbeds processes and SOPs.

Skills

Team leadership

Onboarding experience

Project management

Customer success

Hospitality operations

Executive communication

Multi-property PMS implementations

North American hotel ops

Hiring & coaching

Tools

Salesforce

Oracle Opera

Job description

Cloudbeds seeks a Mid-Market Onboarding Lead for North America to own the onboarding experience for independent hotels, resorts, and multi-property groups moving to Cloudbeds. You will lead the regional team and oversee a small set of strategic NA accounts through go-live and handoff.

This remote-first, player-coach role requires strong hospitality operations knowledge, consultative communication, and a track record of driving successful multi-property PMS implementations.