Mid-Market Onboarding Lead - 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. And we do it with a completely remote team.

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.

What You Bring to the Team

• Team Leadership: 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.
• Quality Assurance: 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.
• Key Account Management: 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.
• Resource Allocation: 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.
• Escalation Management: 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.
• Onboarding & Training: 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.
• Performance Tracking: 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.
• Cross-Functional Collaboration: 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.
• Consultative Depth: 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.
• Partner Coordination: Coordinate with third-party consultants and partners who lead or support implementations for some of our customers.
• Operational Support: 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.
• Efficiency: Use AI and automation to cut administrative work for yourself and your team.

What Sets You Up for Success

• Experience: 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.
• Leadership: 2+ years directly managing customer-facing team members in onboarding, implementation, professional services, or customer success, including hiring, coaching, and performance management.
• Technical Implementation: Hands-on experience leading multi-property or 40+ room full-service hotel PMS implementations, from kickoff through go-live.
• Industry Knowledge: Strong understanding of North American hotel operations: front office, reservations, distribution, revenue management, payments, and reporting.
• Communication: 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: Project-management discipline: scope, milestones, risks, and stakeholder communication across many concurrent projects.
• Data & Tooling: Comfortable with data and tooling: you run your team from dashboards and Salesforce (or a similar CRM), and you adopt AI tools readily.
• Adaptability: 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 & Benefits

• Salary Range: $100,000 - $140,000 USD (for US-based candidates; packages above this range will be considered based on skills and experience).
• Remote Work: Remote First, Remote Always.
• Time Off: PTO in accordance with local labor requirements.
• Parental Leave: Fully Paid Parental Leave.
• Stipends: Home office stipend based on country of residency.
• Professional Development: Courses in Cloudbeds University, manager training, upskilling, and knowledge transfer.

Work Authorization

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.