[All remote jobs](https://jobicy.com/jobs.md)[![Cloudbeds logo](https://jobicy.com/data/server-nyc0409/galaxy/mercury/2025/06/3aef1a38-221.png)](https://jobicy.com/company/cloudbeds.md)[Cloudbeds](https://jobicy.com/company/cloudbeds.md) # Mid-Market Onboarding Lead Review the role, location requirements, compensation details, and application process before deciding whether this opportunity fits your next career move. [Apply for this job](#job-application)[View company](https://jobicy.com/company/cloudbeds.md)ShareRemote from[USA](https://jobicy.com/job-region/usa.md), [Canada](https://jobicy.com/job-region/canada.md)SalaryUSD 100k–140k / yrDepartment[Project & Program Management](https://jobicy.com/categories/project-management.md)EmploymentFull TimeExperienceDirectorPublished22 Oct 2026Apply before21 Nov 2026Listing views22Application actions1Application toolkit ## Make your next move. Prepare your resume, explore your fit, and draft a cover letter for this opportunity. AI Summary ## The role, at a glance. Cloudbeds is seeking a player-coach leader to manage North American onboarding for mid-market hotels, resorts, and multi-property groups adopting its hospitality platform. The role leads Onboarding Project Managers and Coaches while directly overseeing a small portfolio of strategic, complex customer implementations through go-live and handoff. Key outcomes include reducing time-to-live, improving deployment quality and onboarding CSAT, managing escalations, and strengthening early customer retention. Candidates need substantial hotel operations or hospitality technology experience, direct people-management experience, and hands-on PMS implementation expertise. The position requires close cross-functional collaboration with Sales, Account Management, Support, Professional Services, Product, and implementation partners in a remote-first environment. ## Role DNA A quick view of the complexity, pace, ownership and collaboration implied by the job description. ### Job Complexity 5/5EasyHard ### Pace & Pressure 5/5RelaxedFast-paced ### Autonomy Level 5/5GuidedFull ownership ### Communication Load 5/5IndependentCollaborative AI insightThis is a senior operational leadership role combining people management, strategic account ownership, complex PMS deployments, and escalation management. Success requires deep hospitality-domain knowledge and the ability to improve measurable delivery outcomes across multiple concurrent implementations. ## Salary analysis Estimated compensation compared with the broader US market for similar roles. Estimated job median (per year)Market rate$120,000US market range (per year)$105k–$155k0$170.50k AI insightThe employer discloses annual US compensation of $100,000–$140,000 USD, with a midpoint of $120,000. For a North American onboarding leadership role requiring hospitality PMS implementation and people-management experience, the estimated annual market range is $105,000–$155,000 USD. ## Core skills Skills and capabilities most closely associated with this opportunity. [Hospitality technology](https://jobicy.com/jobs?search_keywords=Hospitality%20technology.md)[PMS implementation](https://jobicy.com/jobs?search_keywords=PMS%20implementation.md)[Hotel operations](https://jobicy.com/jobs?search_keywords=Hotel%20operations.md)[Customer onboarding](https://jobicy.com/jobs?search_keywords=Customer%20onboarding.md)[People management](https://jobicy.com/jobs?search_keywords=People%20management.md)[Project management](https://jobicy.com/jobs?search_keywords=Project%20management.md)[Strategic account management](https://jobicy.com/jobs?search_keywords=Strategic%20account%20management.md)[Escalation management](https://jobicy.com/jobs?search_keywords=Escalation%20management.md)[Salesforce](https://jobicy.com/jobs?search_keywords=Salesforce.md)[Customer success](https://jobicy.com/jobs?search_keywords=Customer%20success.md)[Performance coaching](https://jobicy.com/jobs?search_keywords=Performance%20coaching.md)[Cross-functional collaboration](https://jobicy.com/jobs?search_keywords=Cross-functional%20collaboration.md)[Workflow optimization](https://jobicy.com/jobs?search_keywords=Workflow%20optimization.md)[Risk management](https://jobicy.com/jobs?search_keywords=Risk%20management.md)[Process automation](https://jobicy.com/jobs?search_keywords=Process%20automation.md) Sample interview questionsDescribe a complex multi-property PMS implementation you led from kickoff through go-live. How did you manage risks?I would explain the project scope, stakeholder groups, migration or configuration dependencies, and milestone plan. I would highlight how I maintained a risk register, held regular executive checkpoints, used readiness criteria before go-live, and created a Hypercare plan to address issues quickly after launch. How would you improve time-to-live without reducing implementation quality? I would first segment accounts by complexity and establish clear implementation paths, ownership, and entry criteria. I would use dashboards to identify recurring bottlenecks, automate repeatable administrative tasks, strengthen kickoff expectation-setting, and track quality indicators such as configuration completeness, CSAT, and early post-launch issues alongside speed. How do you coach a team member whose customer calls create confusion or escalation risk? I would review specific call recordings with the team member, identify observable behaviors and their customer impact, and agree on a focused improvement plan. This could include structured call preparation, role-play for difficult conversations, clear product-limitation messaging, follow-up observation, and measurable checkpoints. A strategic hotel customer is unhappy shortly before go-live. What actions would you take? I would quickly diagnose the underlying issue by reviewing commitments, scope, configuration status, and stakeholder concerns. I would reset the plan transparently with the customer, assign accountable owners and dates, escalate internally where needed, and remain actively involved until the revised path and customer confidence are restored. How have you used data to manage a customer-facing onboarding or implementation team? I use operational dashboards to monitor workload, milestone health, time-to-live, deployment quality, CSAT, escalations, and early retention signals. I combine these indicators with qualitative call reviews and team feedback to prioritize coaching, rebalance capacity, improve playbooks, and address risks before they affect customer outcomes. Opportunity details ## About this role. What Makes Cloudbeds Unique At [Cloudbeds](https://www.cloudbeds.com/), 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. Imagine working alongside global innovators to build AI-powered solutions that solve hoteliers’ biggest challenges. 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. How You’ll Make an Impact: As Mid-Market Onboarding Lead for North America, you’ll own the onboarding experience for our most important growth market: independent hotels, resorts, and multi-property groups moving to Cloudbeds, often from enterprise systems like Opera. You’ll lead the regional team of Onboarding Project Managers and Mid-Market Coaches who take these customers from signed contract through kickoff, go-live, Hypercare, and a clean handoff to Account Management. This is a player-coach role. You’ll build and run the team, and you’ll also stay close to the work, personally overseeing a small set of our most strategic North American accounts and stepping in when a project is at risk. Our mid-market customers expect a partner who understands their operation, not just our software. You’ll set that standard: consultative kickoffs, clear expectations, and guidance on how their workflows and SOPs should change, not only which buttons to click. You’ll report to the Global Director of Mid-Market Onboarding and work alongside regional leads in LATAM, EMEA, and APAC. You’ll be measured on time-to-live, deployment quality, onboarding CSAT, early-lifecycle retention, and the strength and readiness of your team. Our Mid-Market Onboarding Team: Our Mid-Market Onboarding team is a global group of former hoteliers, project managers, and implementation specialists. We’re purpose-built for complex customers: coaches carry fewer accounts so they can go deeper, every project has structure, and the first days after go-live are covered by a dedicated Hypercare phase. We test and learn constantly, use AI and automation to strip out admin work, and save our time for what matters most: building trust and helping hoteliers run a better operation from day one. Our principle: standardize the repeatable, personalize the meaningful. What You Bring to the Team: * Lead, coach, and develop the North America team of Onboarding Project Managers and Mid-Market Coaches, including team members based in Latin America who serve North American customers, with clear expectations, regular 1:1s, performance management, and growth paths * Raise the bar on customer-facing quality: run call reviews and kickoff prep, and coach the team on tone, how to frame product limitations, and when and how to have hard conversations, so that kickoffs build confidence instead of creating escalations * Personally oversee a small portfolio of strategic North American key accounts and multi-property groups, serving as their senior onboarding contact and staying involved through go-live and handoff * Own account intake and assignment for the region: review key-account and exception requests, match each account to the right OPM or coach based on complexity and capacity, and keep workloads within target * Act as the first escalation point for at-risk North American onboardings. Diagnose what went wrong, reset the plan with the customer, and decide when to bring in Professional Services, certified consultant partners, or a different owner * Ramp new hires quickly: run regional training and shadowing, certify readiness before new team members take live accounts, and help shape hiring profiles as the team grows * Track and improve regional performance on time-to-live, deployment quality, onboarding CSAT, Hypercare outcomes, and early retention, using Salesforce dashboards and onboarding tooling to spot risk early * Partner closely with North American Sales leadership on clean handoffs and realistic expectations, and with Account Management, Hypercare, Support, Professional Services, and Product to close gaps and feed recurring issues back to the right owners * Bring consultative depth to customers switching from other PMS platforms, helping them redesign day-to-day workflows, reporting, and SOPs for how they will run in Cloudbeds * Coordinate with third-party consultants and partners who lead or support implementations for some of our customers * Take on the day-to-day leadership load (team questions, case investigations, call coverage) so the team keeps moving and senior leadership can focus on strategy * Use AI and automation to cut administrative work for yourself and your team What Sets You Up for Success: * 5+ years in hotel operations or hospitality technology (a hotel, hotel group or management company, or a PMS/hospitality software company). Experience limited to OTAs, GDS, or travel distribution does not meet this requirement * 2+ years directly managing customer-facing team members in onboarding, implementation, professional services, or customer success, including hiring, coaching, and performance management * Hands-on experience leading multi-property or 40+ room full-service hotel PMS implementations, from kickoff through go-live * Strong understanding of North American hotel operations: front office, reservations, distribution, revenue management, payments, and reporting * A consultative, hospitality-first communication style with executives and front-line staff alike. You can deliver hard news, reset expectations, and leave the customer more confident than before * Project-management discipline: scope, milestones, risks, and stakeholder communication across many concurrent projects * Comfortable with data and tooling: you run your team from dashboards and Salesforce (or a similar CRM), and you adopt AI tools readily * Calm, organized, and decisive in a fast-growing, remote-first environment where priorities shift quickly Bonus Skills to Stand Out (Optional): * Experience implementing or operating enterprise systems such as Oracle Opera, so you can translate customers’ old workflows into Cloudbeds * Spanish fluency at a business-professional level * PMP or similar project-management certification * Experience working with hotel management companies, hotel consultants, or reseller partners * Familiarity with revenue management systems, guest experience tools, or hospitality payments 𝗖𝗼𝗺𝗽𝗲𝗻𝘀𝗮𝘁𝗶𝗼𝗻: Depending on your skills and experience, you can expect your annual compensation to be between $100,000 and $140,000 USD. Please note that we maintain high flexibility, and packages above this range will be considered. (The salary is only for US-based candidates). Work Authorization: Please note that applicants must be currently authorized to work in the location where the position is located without requiring visa sponsorship. At this time, Cloudbeds is unable to provide sponsorship for work visas. What to Expect – Your Journey with Us Behind Cloudbeds’ revolutionary technology is a team redefining what’s possible in hospitality. We’re 650+ team members across 40+ countries, bringing together elite engineers, AI architects, world-class designers, hoteliers, and hospitality veterans to solve challenges others haven’t dared to tackle. 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. If you’re ready to work alongside some of the brightest minds in tech who are obsessed with using AI to transform a trillion-dollar industry, this is your chance to be part of something extraordinary. Learn more online at [cloudbeds.com](https://www.cloudbeds.com/) Cloudbeds [Awards](https://www.cloudbeds.com/press/?press_type=company-news&news_category=awards): * Winner – Hotel Management Software | HotelTechAwards (2026) * Overall 10 Best Places to Work | HotelTechAwards (2026) * Overall Top 10 Hotelier’s Choice | HotelTechAwards (2026) * Finalist – Property Management Systems (PMS) & Channel Managers | HotelTechAwards (2026) * Most Loved Workplace® Certified (2024) * Deloitte Technology Fast 500 (2024) Discover our Benefits: * Remote First, Remote Always * 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, including manager training, upskilling, and knowledge transfer Everyone is Welcome – A Culture of Inclusion Cloudbeds is proud to be an Equal Opportunity Employer that celebrates the diversity in our global team! We do not discriminate based upon race, religion, color, national origin, gender (including pregnancy, childbirth, or related medical conditions), sexual orientation, gender identity, gender expression, age, status as a protected veteran, status as an individual with a disability, or other applicable legally protected characteristics. Cloudbeds is committed to the full inclusion of all qualified individuals. As part of this commitment, Cloudbeds will ensure that persons with disabilities are provided reasonable accommodations in the hiring process. We encourage deaf, hard-of-hearing, deaf-blind, and deaf-disabled individuals to apply. If reasonable accommodation is needed to participate in the job application or interview process or to perform essential job functions, please contact our HR team by phone at (858) 201-7832 or via email at accommodations@cloudbeds.com. Cloudbeds will provide an American Sign Language (ASL) interpreter where needed as a reasonable accommodation for the hiring process. To all Staffing and Recruiting Agencies: Our Careers Site is only for individuals seeking a job at Cloudbeds. Staffing, recruiting agencies, and individuals being represented by an agency are not authorized to use this site or to submit applications, and any such submissions will be considered unsolicited. Cloudbeds does not accept unsolicited resumes or applications from agencies. Please do not forward resumes to our jobs alias, Cloudbeds employees, or any other company location. Cloudbeds is not responsible for any fees related to unsolicited resumes/applications. 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