Global Director – Mid-Market Onboarding

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

📋 Description

• Take ownership and enhance the onboarding process for Cloudbeds' rapidly expanding and most intricate customer segment.

• Lead the team tasked with supporting mid-market clients from the moment they sign the contract through to go-live, adoption, and their transition to Account Management.

• Develop frameworks, standards, metrics, and team capabilities to deliver a top-notch, repeatable onboarding experience.

• Guide, mentor, and grow the Mid-Market Onboarding team, including Onboarding Project Managers and senior coaches.

• Establish expectations, performance benchmarks, growth pathways, and foster a culture of accountability and ongoing improvement.

• Manage the entire onboarding process from sales handoff to go-live, adoption, and subsequent transition to Account Management.

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

• Create standardized onboarding frameworks, standard operating procedures, and configuration guidelines for complex multi-property deployments ranging from 25 to over 100 rooms.

• Define and manage 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 at risk.

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

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

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

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

• Contribute to the wider strategy for engaging mid-market and enterprise-adjacent clients.

⛳️ Requirements

• Over 7 years of experience in hospitality or hospitality technology, including direct customer onboarding or implementation experience and team leadership.

• Experience working at a hotel, hotel group, or a PMS or hospitality technology company; OTA or travel distribution experience alone is not considered sufficient.

• Demonstrated success in building or significantly enhancing onboarding and implementation functions and frameworks.

• Proven leadership experience in managing people — hiring, coaching, and developing customer-facing teams in a distributed, global context.

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

• In-depth knowledge of hotel operations and the challenges involved in serving multi-property, mid-market hospitality clients.

• Capability to navigate seamlessly between strategy and execution.

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

• Candidates must currently have authorization to work in the location of the position without the need for visa sponsorship.

• Proficiency in additional languages such as Spanish or Portuguese at a business-professional level is preferred.

• Direct experience in onboarding or implementing clients at a hospitality SaaS or PMS organization.

• Familiarity with property management systems, payment processing, or hospitality fintech.

• Experience in establishing onboarding or implementation functions in a scale-up stage company.

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

🏝️ Benefits

• Remote First, Remote Always.

• Paid Time Off in accordance with local labor regulations.

• Fully Paid Parental Leave.

• Home office stipend based on country of residence.

• Professional development courses available through Cloudbeds University.

• Access to professional development opportunities, including manager training, upskilling, and knowledge transfer.