[Hiring] Mid-Market Onboarding Lead @Canada Job Posts

Role Description

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.

Qualifications

• 5+ years in hotel operations or hospitality technology (a hotel, hotel group or management company, or a PMS/hospitality software company).
• 2+ years directly managing customer-facing team members in onboarding, implementation, professional services, or customer success.
• 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.
• 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).
• Calm, organized, and decisive in a fast-growing, remote-first environment where priorities shift quickly.

Requirements

• Lead, coach, and develop the North America team of Onboarding Project Managers and Mid-Market Coaches.
• Raise the bar on customer-facing quality: run call reviews and kickoff prep.
• Personally oversee a small portfolio of strategic North American key accounts and multi-property groups.
• Own account intake and assignment for the region.
• Act as the first escalation point for at-risk North American onboardings.
• Ramp new hires quickly: run regional training and shadowing.
• Track and improve regional performance on time-to-live, deployment quality, onboarding CSAT, Hypercare outcomes, and early retention.
• Partner closely with North American Sales leadership on clean handoffs and realistic expectations.
• Bring consultative depth to customers switching from other PMS platforms.
• Coordinate with third-party consultants and partners who lead or support implementations.
• Take on the day-to-day leadership load (team questions, case investigations, call coverage).
• Use AI and automation to cut administrative work for yourself and your team.

Benefits

• Work from home in eligible locations across Canada, with flexibility to work and travel in accordance with company policies.
• Open PTO beyond statutory minimums, paid Canadian holidays, and 5 paid sick days.
• Cloudbeds matches 100% of your contributions, up to 4% of eligible earnings.
• Extended healthcare coverage, including prescription drugs, dental, vision, and paramedical services for you and your eligible dependents.
• Company-paid Life & AD&D insurance (3x annual earnings, up to $500,000), with disability and critical illness coverage also available.
• Paid maternity and partner leave, plus confidential 24/7 Employee Assistance Program (EAP) support.
• A one-time home office setup stipend and recurring WiFi and phone stipends.
• Professional development through Cloudbeds University and 1 paid Volunteer Day per quarter through Cloudbeds Cares.