Mid-Market Onboarding Lead

As Mid-Market Onboarding Lead for North America, you will own the onboarding experience for independent hotels, resorts, and multi-property groups moving to Cloudbeds, often from enterprise systems like Opera. You will lead the regional team of Onboarding Project Managers and Mid-Market Coaches from signed contract through kickoff, go-live, Hypercare, and handoff to Account Management. This is a player-coach role. You will report to the Global Director of Mid-Market Onboarding and work alongside regional leads in LATAM, EMEA, and APAC. You will be measured on time-to-live, deployment quality, onboarding CSAT, early-lifecycle retention, and the strength and readiness of your team.

Responsibilities

Lead, coach, and develop the North America team of Onboarding Project Managers and Mid-Market Coaches; Raise the bar on customer-facing quality through call reviews, kickoff prep, and coaching; Personally oversee a small portfolio of strategic North American key accounts and multi-property groups as senior onboarding contact; Own account intake and assignment for the region, matching accounts to the right OPM or coach and keeping workloads within target; Act as first escalation point for at-risk North American onboardings and decide when to bring in Professional Services, certified consultant partners, or a different owner; Ramp new hires through regional training, shadowing, and readiness certification; Track and improve regional performance on time-to-live, deployment quality, onboarding CSAT, Hypercare outcomes, and early retention; Partner with North American Sales leadership, Account Management, Hypercare, Support, Professional Services, and Product; Bring consultative depth to customers switching from other PMS platforms, redesigning workflows, reporting, and SOPs; Coordinate with third-party consultants and partners leading or supporting some implementations; Take on day-to-day leadership load (team questions, case investigations, call coverage); Use AI and automation to cut administrative work

Requirements

5+ years in hotel operations or hospitality technology (a hotel, hotel group or management company, or a PMS/hospitality software company), not limited to OTAs, GDS, or travel distribution; 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, stakeholder communication across many concurrent projects); Comfortable with data and tooling (dashboards and Salesforce or a similar CRM) and adopts AI tools readily; Calm, organized, and decisive in a fast-growing, remote-first environment; Applicants must be currently authorized to work in the location without visa sponsorship (Cloudbeds cannot sponsor work visas)

Nice to have

Experience implementing or operating enterprise systems such as Oracle Opera; Spanish fluency at a business-professional level; PMP or similar project-management certification; Experience working with hotel management companies, hotel consultants, or reseller partners; Familiarity with revenue management systems, guest experience tools, or hospitality payments

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