Mid Market Onboarding Coach

Location: Remote

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 and its features, helping them align technology with their operational goals and business objectives. This role requires a consultative mindset, 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, empowering clients to use our platform to deliver an experience of Unreasonable Hospitality. We're looking for someone who truly understands hospitality and personalizes every interaction to demonstrate how Cloudbeds helps customers operate more efficiently and grow their business. You'll care for our customers and their properties just as you would for a guest in a hotel—always going the extra mile.

Our Customer Onboarding Team

Our Onboarding team is where Hospitality Hearts meet Smart Solutions. We are 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 and strengthening relationships and ensuring our customers feel confident and supported from day one.

If you are driven by emotional intelligence, trust-building, and delivering deeply personalized hospitality moments instead of repetitive operational tasks, you will feel right at home here.

As a Mid Market Onboarding Coach, you'll collaborate closely with Onboarding Project Management and cross-functional partners to deliver a seamless onboarding experience for some of our most strategic and operationally complex customers.

What You Bring to the Team

• Champion the core principle: Standardize the repeatable, personalize the meaningful.
• Eagerly adopt AI and tooling to handle administrative work and repetitive training questions, freeing you to focus on strategic onboarding guidance, relationship building, and product adoption.
• 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.
• Manage and guide the onboarding experience for assigned mid-market properties, ensuring customer readiness, successful adoption, and confidence using the Cloudbeds platform.
• Guide customers through system setup, configuration, operational workflows, and best practices tailored to their business needs.
• Build trusted relationships with property leadership, owners, and key stakeholders to align onboarding objectives with business goals and operational outcomes.
• Partner closely with Onboarding Project Management to execute onboarding plans, manage dependencies, and ensure customers achieve critical implementation milestones.
• Collaborate with Sales, Product, Customer Success, Support, and Onboarding Project Management to convert onboarding feedback into systemic operational improvements and ensure Cloudbeds' value is realized early.
• Facilitate the customer journey from onboarding and training through hypercare and transition to ongoing support via video, phone, and email.
• Own the customer relationship throughout the onboarding experience, resolving questions and coordinating solutions for escalated issues across multiple channels.
• Act as a strategic consultant throughout the onboarding journey, helping customers optimize operational processes and maximize the value of the Cloudbeds platform.
• Drive customer adoption and long-term success by identifying opportunities to expand utilization of Cloudbeds features, integrations, and best practices.
• Partner with Sales to define success, demonstrate ROI, and support customer retention and long-term growth.
• Build strong customer relationships that drive platform adoption, engagement, and loyalty.
• Develop a deep understanding of Cloudbeds' products, integrations, and customer needs.
• Deliver consultative training and coaching that empowers customers to successfully learn, adopt, and maximize the value of Cloudbeds features and functionality.
• Support complex onboarding engagements by proactively identifying risks, removing obstacles, and coordinating cross-functional resources to drive successful customer outcomes.
• Embody the Caring Rebel mindset, ensuring full client context is maintained throughout the onboarding journey and that new knowledge is captured, searchable, and reusable for future customers.
• Contribute to training materials, onboarding best practices, and knowledge capture while staying current on system enhancements and new product capabilities.
• Maintain accurate records of customer activities in Salesforce, gather customer feedback, and share insights that help improve the customer experience and product roadmap.
• Other projects/duties as requested.

What Sets You Up for Success

• Show strong AI Smarts: Exceptional technical aptitude and learning agility. You pick up new tools quickly, understand how to leverage AI to unlock time to focus on delivering personalized customer relationships, and thrive in environments where technology and processes are constantly evolving.
• Demonstrate your Hospitality Heart: Proven ability in emotional intelligence and trust-building. You are an Empathy Champion—comfortable engaging directly with customers at all levels to navigate their unique business challenges and ensure they feel truly cared for throughout the onboarding process.
• Bring 4+ years of hospitality operations experience, preferably in leadership or senior operational roles within hotels, resorts, hotel groups, or hospitality management companies.
• 2+ years of SaaS onboarding, implementation, customer success, account management, or customer-facing software experience is preferred.
• Demonstrate expertise in hotel operations, including front office, reservations, revenue management, guest services, distribution, and property management systems.
• Experience managing complex customer onboarding, implementation, training, change management, or customer success initiatives.
• Ability to engage and influence stakeholders at multiple levels, from operational users to property leadership and executive decision-makers.
• Strong consultative, problem-solving, and project coordination skills, with the ability to manage multiple high-value customer engagements simultaneously.
• Proven ability to drive customer adoption, operational improvements, and business outcomes through technology solutions.
• Communicate product offerings clearly and synthesize customer feedback into actionable insights for internal teams.
• Share customer insights and opportunities across departments to drive alignment and continuous improvement.
• Empower clients to become self-sufficient during onboarding and beyond.
• Deliver exceptional communication with empathy and a customer-focused approach.
• Experience working with hospitality technology solutions such as PMS, CRS, Channel Managers, Revenue Management Systems, or related hotel software is strongly preferred.
• Experience supporting multi-property operators, hotel groups, or more complex hospitality organizations is a plus.
• Experience leading operational transformation, technology rollouts, or process improvement initiatives within hospitality organizations is a plus.
• Comfortable working cross-functionally in a fast-paced, remote-first environment while balancing multiple priorities and customer needs.