Director, Mid-Market Onboarding - Mid-Market Onboarding

𝗛𝗼𝘄 𝗬𝗼𝘂'𝗹𝗹 𝗠𝗮𝗸𝗲 𝗮𝗻 𝗜𝗺𝗽𝗮𝗰𝘁:

As 𝗚𝗹𝗼𝗯𝗮𝗹 𝗗𝗶𝗿𝗲𝗰𝘁𝗼𝗿, 𝗠𝗶𝗱-𝗠𝗮𝗿𝗸𝗲𝘁 𝗢𝗻𝗯𝗼𝗮𝗿𝗱𝗶𝗻𝗴, you will own and scale the onboarding function for Cloudbeds' fastest-growing and most complex customer segment. You'll lead the team responsible for guiding mid-market customers from contract signature through go-live, adoption, and a clean transition to Account Management. You'll build the frameworks, standards, metrics, and team capability that make that experience world-class and repeatable at scale.

You'll inherit a team of dedicated ICs and leads that have been experimenting with new ways to support these customers and improve their experience. Your charter is to get leadership in place and be maniacal about customer experience while building the project-management rigor that complex mid-market deployments demand. You'll be measured on onboarding velocity, deployment quality, customer satisfaction, and the long-term retention impact of a strong start.

𝗢𝘂𝗿 𝗢𝗻𝗯𝗼𝗮𝗿𝗱𝗶𝗻𝗴 𝗧𝗲𝗮𝗺:

Our team is passionate about delivering exceptional customer experiences and helping hoteliers succeed with Cloudbeds from day one. We build together with a test-and-learn mindset that encourages innovation, collaboration, and continuous improvement. Every team member is valued and empowered to share feedback, ideas, and insights so we can learn, grow, and improve both as individuals and as a team. Leaders who thrive here are proactive communicators, collaborative problem-solvers, and true customer advocates who enjoy navigating complexity while building the systems and people that scale it.

𝗪𝗵𝗮𝘁 𝗬𝗼𝘂 𝗕𝗿𝗶𝗻𝗴 𝘁𝗼 𝘁𝗵𝗲 𝗧𝗲𝗮𝗺:

• Lead, coach, and develop the Mid-Market Onboarding team — including Onboarding Project Managers and senior coaches — setting clear expectations, performance standards, growth paths, and a culture of accountability and continuous improvement
• Own end-to-end onboarding outcomes for mid-market customers from sales handoff through go-live, adoption, and transition to Account Management — diagnosing and fixing execution gaps in training quality, error detection, and deployment velocity
• Build standardized onboarding frameworks, SOPs, and configuration standards for complex multi-property and 25–100+ room deployments that balance customization with scalability
• Establish and own the metrics that matter: onboarding velocity, deployment quality scores, training completion, CSAT/NPS, and early-lifecycle retention — monitoring portfolio health and intervening early on at-risk projects
• Own capacity and staffing planning for the division — forecasting demand, balancing workload across the team, and partnering with leadership on headcount decisions
• Serve as a senior escalation point for complex or at-risk mid-market deployments and partner with Account Management on clean, trust-preserving handoffs
• Partner cross-functionally with Sales, Product, Support, Professional Services, and Account Management — bridging what gets sold and what gets delivered, and contributing to the broader strategy for how Cloudbeds serves mid-market and enterprise-adjacent customers

𝗪𝗵𝗮𝘁 𝗦𝗲𝘁𝘀 𝗬𝗼𝘂 𝗨𝗽 𝗳𝗼𝗿 𝗦𝘂𝗰𝗰𝗲𝘀𝘀:

• 7+ years in hospitality or hospitality technology, including hands-on customer onboarding or implementation experience and team leadership (time at a hotel, hotel group, or a PMS or hospitality-tech company; OTA or travel-distribution experience on its own does not count)
• Track record of building or significantly improving onboarding and implementation functions and frameworks
• Proven people-leadership experience — hiring, coaching, and developing customer-facing teams in a distributed, global environment
• Strong project-management foundation: scope, milestones, timelines, and risk mitigation applied to complex multi-stakeholder deployments
• Deep understanding of hotel operations and the complexity of serving multi-property, mid-market hospitality customers
• Ability to move fluidly between strategy and execution — you can design the framework and roll up your sleeves to implement it
• Data-driven: comfortable with KPIs, dashboards, and using insights to drive decisions

𝗕𝗼𝗻𝘂𝘀 𝗦𝗸𝗶𝗹𝗹𝘀 𝘁𝗼 𝗦𝘁𝗮𝗻𝗱 𝗢𝘂𝘁:

• Additional language fluency (Spanish, Portuguese) at a business-professional level
• Direct experience onboarding or implementing customers at a hospitality SaaS or PMS company
• Familiarity with property management systems, payments, or hospitality fintech
• Experience building onboarding or implementation functions at a scale-up stage company
• Background working with hotel management companies, small chains, or the consultant ecosystem

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