Mid Market Onboarding Coach - Cloudbeds

About Cloudbeds

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.

How You'll Make an Impact

As a Mid Market Onboarding Coach, you will empower our mid-market customers to transform their properties through our AI Smarts + Hospitality Hearts mission. You will manage and guide the onboarding experience for mid-market properties, serving as a trusted advisor and strategic partner throughout implementation, training, adoption, and launch.

Leveraging your firsthand hospitality operations experience, you won't just teach the system—you will help hoteliers design processes that eliminate friction, allowing them to focus on their guests. You will guide customers through the successful setup, learning, adoption, and optimization of the Cloudbeds platform, balancing hospitality expertise with technical proficiency to ensure customers realize value quickly and confidently.

Responsibilities

• Serve as the trusted advisor for assigned mid-market customers, providing strategic guidance on operational workflows, change management, system configuration, and platform adoption throughout the onboarding journey.
• Own the customer relationship end-to-end—guiding system setup, resolving escalated issues across channels, and facilitating the journey from onboarding through hypercare and transition to ongoing support.
• Build trusted relationships with property leadership, owners, and key stakeholders, partnering with Onboarding Project Management to execute plans and hit critical implementation milestones.
• Act as a strategic consultant throughout onboarding, identifying opportunities to expand platform/feature adoption and driving long-term customer success.
• Collaborate with Sales, Product, Customer Success, and Support to convert onboarding feedback into systemic improvements and ensure Cloudbeds' value is realized early.
• Deliver consultative training and coaching that empowers customers to confidently learn, adopt, and maximize platform value, while proactively identifying and removing risks in complex engagements.
• Champion "standardize the repeatable, personalize the meaningful"—adopting AI and tooling to handle administrative work, freeing you to focus on relationship-building and strategic guidance.

Requirements

• 4+ years of hospitality operations experience, preferably in leadership or senior operational roles within hotels, resorts, hotel groups, or hospitality management companies.
• Demonstrated expertise in hotel operations, including front office, reservations, revenue management, guest services, distribution, and property management systems.
• 2+ years of SaaS onboarding, implementation, customer success, account management, or customer-facing software experience preferred.
• Proven ability in emotional intelligence and trust-building, comfortable engaging directly with customers at all levels—from operational users to executive decision-makers.
• Strong consultative, problem-solving, and project coordination skills, managing multiple high-value, complex customer engagements simultaneously.
• Exceptional technical aptitude and learning agility, with the ability to leverage AI and quickly adopt new tools in a constantly evolving environment.
• Work authorization to work in your region without requiring visa sponsorship.

Bonus Qualifications

• Experience supporting multi-property operators, hotel groups, or more complex hospitality organizations.
• Experience leading operational transformation, technology rollouts, or process improvement initiatives within hospitality organizations.
• Experience working with hospitality technology solutions (PMS, CRS, Channel Managers, Revenue Management Systems, or related hotel software).

Benefits

• Remote First, Remote Always work culture
• Paid Time Off (PTO) in accordance with local labor requirements
• Fully Paid Parental Leave
• Home office stipend based on country of residency
• Professional development courses in Cloudbeds University
• Access to professional development, manager training, upskilling, and knowledge transfer