At Cloudbeds , we're not just building software, we're transforming hospitality. Our platform powers hotels across 150 countries, processing billions in bookings annually. From boutique properties to large hotel groups, we help hoteliers transform operations and uplevel their commercial strategy through a unified platform that integrates with hundreds of partners. And we do it with a completely remote team. Since our founding in 2012, we've continually been recognized for excellence, most recently earning top honors at the 2026 HotelTechAwards for Best Hotel Management Software and landing on Deloitte's Technology Fast 500 again, but we're just getting started. 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 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 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. 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. 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, Qualified 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. 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. 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. Experience building onboarding or implementation functions at a scale‑up stage company. Background working with hotel management companies, small chains, or the consultant ecosystem. Our diverse team speaks 30+ languages, but we all share one language: a passion for innovation and travel. From pioneering breakthroughs in machine learning to revolutionizing how hotels operate, we're not just watching the future of hospitality unfold – we're coding it, designing it, writing it, and shipping it. Winner – Hotel Management So

📌 ( remote ) Head of Market (Winnipeg)
🏢 Cloudbeds
📍 Winnipeg