Mid Market Onboarding Coach

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. This is a role for a Caring Rebel who models Hospitality Before Efficiency—someone who understands hospitality and personalizes every interaction, caring for our customers just as you would for a guest in a hotel.

Our Customer Onboarding Team:

Our Onboarding team is where Hospitality Hearts meet Smart Solutions. We're a fully remote group of former hoteliers and customer experience professionals focused on removing unnecessary manual work so we can spend more time on our "human magic": building relationships and ensuring customers feel confident and supported from day one. As a Mid Market Onboarding Coach, you'll collaborate closely with Onboarding Project Management and cross-functional partners to deliver a seamless experience for some of our most strategic and operationally complex customers.

What You Bring to the Team:

• 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

What Sets You Up for Success:

• 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—to ensure they feel genuinely cared for
• 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
• Experience working with hospitality technology solutions (PMS, CRS, Channel Managers, Revenue Management Systems, or related hotel software) strongly preferred

Bonus Skills to Stand Out:

• 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