C
Mid-Market Onboarding Lead
Contract type
Ongoing
Work mode
Remote · North America
Experience
Senior · 5+ years
Job description
Lead the North America Mid-Market Onboarding team at Cloudbeds, a player-coach role managing Onboarding Project Managers and Mid-Market Coaches while personally overseeing strategic accounts from contract through go-live and Hypercare.
At a glance
- Employment
- Full-time · Employee (employment agreement)
- Work mode
- Remote · North America
- Pay
- USD 100,000 – 140,000 / year
What you'll do
- 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
- 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 we're looking for
- 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; 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: run the team from dashboards and Salesforce (or a similar CRM), and adopt AI tools readily
- Calm, organized, and decisive in a fast-growing, remote-first environment where priorities shift quickly
- Applicants must be currently authorized to work in the location where the position is located without requiring visa sponsorship
Nice to have
- 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
Your team
Mid-Market Onboarding Team
A global group of former hoteliers, project managers, and implementation specialists, 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.
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
Apply
About Cloudbeds
The leading platform for independent hotels, one powerful platform to run your property
Cloudbeds' 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. Founded in 2012, Cloudbeds is a completely remote team of 650+ team members across 40+ countries.
Mission
We're not just building software, we're transforming hospitality.
Key facts
- 650+ team members
- 2012
- Hospitality technology / software
- Platform powers hotels across 150 countries
- Processes billions in bookings annually
- Integrates with hundreds of partners
- Completely remote team across 40+ countries
- Team speaks 30+ languages
- 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)
What they value
- Standardize the repeatable, personalize the meaningful
- Everyone is Welcome - A Culture of Inclusion