[Hiring] Mid-Market Onboarding Lead @Third-Party Job Posts

Role Description

As Mid-Market Onboarding Lead for North America, you'll own the onboarding experience for our most important growth market: independent hotels, resorts, and multi-property groups moving to Cloudbeds, often from enterprise systems like Opera. You'll lead the regional team of Onboarding Project Managers and Mid-Market Coaches who take these customers from signed contract through kickoff, go-live, Hypercare, and a clean handoff to Account Management.

This is a player-coach role. You'll build and run the team, and you'll also stay close to the work, personally overseeing a small set of our most strategic North American accounts and stepping in when a project is at risk. Our mid-market customers expect a partner who understands their operation, not just our software. You'll set that standard:

• Consultative kickoffs
• Clear expectations
• Guidance on how their workflows and SOPs should change

You'll report to the Global Director of Mid-Market Onboarding and work alongside regional leads in LATAM, EMEA, and APAC. You'll be measured on:

• Time-to-live
• Deployment quality
• Onboarding CSAT
• Early-lifecycle retention
• The strength and readiness of your team

Qualifications

• 5+ years in hotel operations or hospitality technology (a hotel, hotel group or management company, or a PMS/hospitality software company)
• 2+ years directly managing customer-facing team members in onboarding, implementation, professional services, or customer success
• 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
• A consultative, hospitality-first communication style with executives and front-line staff alike
• Project-management discipline: scope, milestones, risks, and stakeholder communication across many concurrent projects
• Comfortable with data and tooling: you run your team from dashboards and Salesforce (or a similar CRM)
• Calm, organized, and decisive in a fast-growing, remote-first environment

Requirements

• Lead, coach, and develop the North America team of Onboarding Project Managers and Mid-Market Coaches
• Raise the bar on customer-facing quality: run call reviews and kickoff prep
• Personally oversee a small portfolio of strategic North American key accounts
• Own account intake and assignment for the region
• Act as the first escalation point for at-risk North American onboardings
• Ramp new hires quickly: run regional training and shadowing
• Track and improve regional performance on time-to-live, deployment quality, onboarding CSAT, Hypercare outcomes, and early retention
• Partner closely with North American Sales leadership on clean handoffs and realistic expectations
• Bring consultative depth to customers switching from other PMS platforms
• Coordinate with third-party consultants and partners who lead or support implementations
• Take on the day-to-day leadership load (team questions, case investigations, call coverage)
• Use AI and automation to cut administrative work for yourself and your team

Benefits

• 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