Remote Mid-Market Onboarding Lead, NA

Cloudbeds; Philadelphia (Philadelphia County); Remote; USD 100,000 - 140,000; Full time

Benefits offered by this job

Remote-first culture

Remote work

PTO

Fully paid parental leave

Home office stipend

Professional development

Job summary

Cloudbeds, a remote-first hospitality platform, seeks a Mid-Market Onboarding Lead for North America. You will guide a regional team of Onboarding Project Managers and Mid-Market Coaches, overseeing strategic accounts from signed contract through go-live and handoff.

You’ll combine hands-on coaching with high‑level account leadership, shaping workflows, SOPs, and timelines while ensuring time-to-live, deployment quality, and CSAT goals across a growing North American portfolio.

Qualifications

• 5+ years in hotel operations or hospitality technology (a hotel, hotel group or PMS company).
• 2+ years directly managing customer-facing team members in onboarding, implementation, professional services, or customer success.
• Hands-on experience leading multi-property PMS implementations, from kickoff through go-live.
• Strong understanding of North American hotel operations: front office, reservations, distribution, revenue management, payments, reporting.
• Consultative, hospitality-first communication with executives and front-line staff; able to reset expectations and build trust.
• Project-management discipline: scope, milestones, risks, stakeholder communication across many projects.
• Comfortable with data and tooling; manage teams via dashboards and CRM; adopt AI tools.
• Calm, organized, and decisive in a fast-growing, remote-first environment.
• Experience implementing or operating enterprise systems such as Oracle Opera.
• Spanish fluency at business level.
• PMP or similar project-management certification.
• Experience working with hotel management companies, consultants, or resellers.
• Familiarity with revenue management systems, guest experience tools, or hospitality payments

Responsibilities

• Lead, coach, and develop the North America team of Onboarding Project Managers and Mid-Market Coaches with clear expectations and growth paths.
• Raise the bar on customer-facing quality: run call reviews, kickoff prep, and coach tone and framing of product limitations.
• Personally oversee a small portfolio of strategic North American accounts through go-live and handoff.
• Own account intake and assignment for the region; match accounts to the right coach based on complexity and capacity.
• Act as escalation point for at‑risk onboardings; reset plans and decide on involvement of professional services or partners.
• Ramp new hires quickly: regional training and shadowing; certify readiness before live accounts.
• Track regional performance on time-to-live, deployment quality, onboarding CSAT, and early retention using Salesforce dashboards.
• Partner with North American Sales, Account Management, Hypercare, Support, and Product to close gaps and feed issues back to owners.
• Bring consultative depth to customers switching from other PMS platforms; redesign workflows, reporting, and SOPs for Cloudbeds.
• Coordinate with third-party consultants and partners who lead or support implementations.
• Take on day-to-day leadership load to keep the team moving and leadership focused on strategy.
• Use AI to cut administrative work for the team and yourself.
• 5+ years in hotel operations or hospitality tech; 2+ years managing onboarding teams; PMP preferred.

Skills

Hotel operations

Hospitality technology

People leadership

Onboarding

Account management

PMP certification

Spanish fluency

Enterprise systems

Project management

Tools

Salesforce

Job description

Cloudbeds, a remote-first hospitality platform, seeks a Mid-Market Onboarding Lead for North America. You will guide a regional team of Onboarding Project Managers and Mid-Market Coaches, overseeing strategic accounts from signed contract through go-live and handoff.

You’ll combine hands-on coaching with high‑level account leadership, shaping workflows, SOPs, and timelines while ensuring time-to-live, deployment quality, and CSAT goals across a growing North American portfolio.