Global Director, Mid-Market Onboarding

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

📋 Description

• Lead, mentor, and enhance the Mid-Market Onboarding team, which includes Onboarding Project Managers and senior coaches.

• Take ownership of the complete onboarding process from the sales handoff to go-live, adoption, and transition to Account Management.

• Identify and resolve execution gaps in training quality, error detection, and deployment speed.

• Develop standardized onboarding frameworks, standard operating procedures (SOPs), and configuration standards for complex multi-property deployments of 25–100+ rooms.

• Define and manage key metrics such as onboarding speed, deployment quality scores, training completion rates, CSAT/NPS, and early-lifecycle retention.

• Oversee portfolio health and proactively intervene in projects that are at risk.

• Manage capacity and staffing planning, forecast demand, balance workloads, and collaborate with leadership on headcount decisions.

• Act as a senior escalation point for complex or high-risk mid-market deployments.

• Collaborate with Account Management to ensure seamless, trust-preserving handoffs.

• Work cross-functionally with Sales, Product, Support, Professional Services, and Account Management.

• Contribute to the overall strategy for serving mid-market and enterprise-adjacent customers.

⛳️ Requirements

• Over 7 years of experience in hospitality or hospitality technology, with hands-on customer onboarding or implementation experience and team leadership.

• Proven history of developing or significantly enhancing onboarding and implementation functions and frameworks.

• Demonstrated people-leadership experience — hiring, coaching, and developing customer-facing teams in a distributed, global environment.

• Strong foundation in project management: managing scope, milestones, timelines, and risk mitigation for complex multi-stakeholder deployments.

• In-depth understanding of hotel operations and the complexities of serving multi-property, mid-market hospitality clients.

• Ability to navigate seamlessly between strategic planning and execution.

• Proficient with KPIs, dashboards, and utilizing insights to inform decision-making.

• Candidates must currently be authorized to work in the location of the position without requiring visa sponsorship.

• Fluency in Spanish or Portuguese at a business-professional level is an additional asset.

• Direct experience in onboarding or implementing customers at a hospitality SaaS or PMS company is a plus.

• Familiarity with property management systems, payments, or hospitality fintech is an added advantage.

• Experience in building onboarding or implementation functions in a scale-up stage company is a bonus.

• Background in working with hotel management companies, small chains, or the consulting ecosystem is a bonus.

🏝️ Benefits

• Remote First, Remote Always.

• Paid Time Off (PTO) in accordance with local labor regulations.

• 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.