Remote North America Mid‑Market Onboarding Lead

Cloudbeds; Madison (WI); Remote; USD 100,000 - 140,000; Full time

Benefits offered by this job

Remote First

Remote Always

PTO

Fully Paid Parental Leave

Home office stipend

Professional development

Job summary

Cloudbeds is seeking a Mid-Market Onboarding Lead for North America to captain the onboarding experience for independent hotels, resorts, and multi-property groups migrating to Cloudbeds. You will lead a regional team of Onboarding Project Managers and Mid-Market Coaches, overseeing go-live, Hypercare, and handoffs.

This player-coach role requires hands-on leadership with strategic accounts, consultative kickoffs, and strong collaboration across Sales, Support, and Product.

Qualifications

• 5+ years in hotel operations or hospitality technology.
• 2+ years directly managing customer-facing team members in onboarding or related functions.
• Hands-on leadership of multi-property PMS implementations from kickoff to go-live.
• Strong understanding of North American hotel operations: front desk, distribution, revenue management.

Responsibilities

• Lead and develop the North America onboarding team with clear expectations and growth paths.
• Coach the team on tone, framing product limitations, and handling hard conversations during kickoffs.
• Oversee a portfolio of strategic North American accounts through go-live and handoff to ensure success.
• Manage account intake and assignment to balance workloads and maximize capacity.
• Ramp new hires with regional training and certification readiness.

Skills

Hotel operations

Team leadership

Onboarding

Multi-property PMS

Sales collaboration

Project management

Customer success

PMP certification

Tools

Salesforce

Job description

Cloudbeds is seeking a Mid-Market Onboarding Lead for North America to captain the onboarding experience for independent hotels, resorts, and multi-property groups migrating to Cloudbeds. You will lead a regional team of Onboarding Project Managers and Mid-Market Coaches, overseeing go-live, Hypercare, and handoffs.

This player-coach role requires hands-on leadership with strategic accounts, consultative kickoffs, and strong collaboration across Sales, Support, and Product.