Mid-Market Onboarding Lead

Canada Job Posts; Canada; Remote; CAD 110,000 - 170,000; Full time

Benefits offered by this job

Remote work Canada

Open PTO & holidays

Retirement savings match

Health, dental & vision insurance

Job summary

Cloudbeds is seeking a Mid-Market Onboarding Lead for North America to own onboarding for independent hotels and multi-property groups transitioning to Cloudbeds. You will lead a regional team of Onboarding Project Managers and Mid-Market Coaches, guiding implementations from contract through go-live and handoff.

You will also personally oversee strategic North American accounts, drive consultative kickoffs, and ensure smooth operations while collaborating with regional leaders in LATAM, EMEA,

Qualifications

• 5+ years in hotel operations or hospitality technology
• 2+ years directly managing customer-facing team members in onboarding/implementation/customer success
• Hands-on experience leading multi-property PMS implementations
• Strong understanding of North American hotel operations
• Consultative, hospitality-first communication style
• Project-management discipline
• Comfortable with data and tooling (dashboards, CRM)
• Calm, organized and decisive in a remote-first environment

Responsibilities

• Lead, coach, and develop the North America onboarding team of Project Managers and Coaches
• Oversee a small portfolio of strategic North American accounts through go-live and handoff
• Own account intake and region assignment based on complexity and capacity
• Act as escalation point for at-risk onboardings and reset plans with customers
• Ramp new hires: regional training and readiness
• Track regional performance with dashboards and Salesforce insights
• Partner with North American Sales and with Account Management, Hypercare, and Product to close gaps and feed issues back to owners
• Provide consultative support for customers migrating from other PMS platforms
• Coordinate with third-party consultants and partners during implementations
• Maintain day-to-day leadership load to keep the team moving
• Leverage AI and automation to reduce administrative work

Skills

Team leadership

Coaching

Customer success

Account management

Data analysis

AI tools

Project management

Salesforce

Tools

Salesforce

Oracle Opera

Job description

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. 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-Maret 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

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.

• 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)

Discover Our Canada Benefits

At Cloudbeds, we believe great work deserves great benefits. Here's how we support your well-being, growth, and life beyond work.

• #RemoteFirst: Work from home in eligible locations across Canada, with flexibility to work and travel in accordance with company policies.
• Time Off & Wellness: Open PTO beyond statutory minimums, paid Canadian holidays, and 5 paid sick days.
• Retirement Savings: Cloudbeds matches 100% of your contributions, up to 4% of eligible earnings.
• Health, Dental & Vision: Extended healthcare coverage, including prescription drugs, dental, vision, and paramedical services for you and your eligible dependents.
• Life & Disability Protection: Company-paid Life & AD&D insurance (3x annual earnings, up to $500,000), with disability and critical illness coverage also available.
• Family & Mental Health: Paid maternity and partner leave, plus confidential 24/7 Employee Assistance Program (EAP) support.