Mid-Market Onboarding Lead

This is a fully remote position, open to applicants in United States.

📋 Description

• Lead, mentor, and develop the North American team of Onboarding Project Managers and Mid-Market Coaches.

• Establish clear expectations, conduct one-on-one meetings, manage performance, and create growth paths.

• Facilitate call reviews and preparation for kickoffs; coach on customer engagement quality and challenging discussions.

• Personally manage strategic key accounts and multi-property groups in North America through the go-live process and handoff.

• Oversee regional account intake and allocation based on complexity and workload capacity.

• Act as the primary escalation point for at-risk onboardings in North America.

• Identify issues, realign customer plans, and collaborate with Professional Services, partners, or alternative owners as necessary.

• Train and certify new team members prior to their engagement with live accounts.

• Monitor and enhance time-to-live, deployment quality, onboarding CSAT, Hypercare results, and early retention utilizing Salesforce dashboards and onboarding tools.

• Collaborate with Sales, Account Management, Hypercare, Support, Professional Services, Product, consultants, and implementation partners.

• Assist customers transitioning from other PMS platforms in redesigning workflows, reporting, and standard operating procedures (SOPs).

• Address team inquiries, investigate cases, and ensure call coverage.

• Leverage AI and automation to minimize administrative tasks.

⛳️ Requirements

• Over 5 years of experience in hotel operations or hospitality technology; experience limited to OTAs, GDS, or travel distribution does not fulfill this requirement.

• A minimum of 2 years of direct management of customer-facing team members in onboarding, implementation, professional services, or customer success, including hiring, coaching, and performance management.

• Practical experience in leading multi-property or full-service hotel PMS implementations of 40+ rooms from kickoff to go-live.

• Comprehensive understanding of North American hotel operations, including front office, reservations, distribution, revenue management, payments, and reporting.

• A consultative, hospitality-oriented communication style when engaging with executives and frontline staff.

• Proficient in project management covering scope, milestones, risks, and stakeholder communication across multiple concurrent projects.

• Comfortable working with data, dashboards, Salesforce or similar CRM, and AI tools.

• Calm, organized, and decisive in a rapidly growing, remote-first setting.

• Currently authorized to work in the location where the position is based without requiring visa sponsorship.

🏝️ Benefits

• Remote First, Remote Always.

• PTO in accordance with local labor laws.

• Fully Paid Parental Leave.

• Home office stipend based on the country of residency.

• Access to professional development courses through Cloudbeds University.

• Opportunities for professional growth, including manager training, upskilling, and knowledge transfer.

• Reasonable accommodations provided during the hiring process and for essential job functions.