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Cloudbeds

Global Director, Mid-Market Onboarding

Reposted 2 Months Ago
Remote
Hiring Remotely in Canada
Senior level
Remote
Hiring Remotely in Canada
Senior level
Lead and scale mid-market onboarding from contract to go-live and handoff. Build frameworks, SOPs, metrics, and staffing plans; improve deployment velocity, quality, training, and early retention. Manage escalations, partner cross-functionally with Sales/Product/Support/Account Management, and coach a distributed team to deliver repeatable, high-quality multi-property implementations.
The summary above was generated by AI

𝗪𝗵𝗮𝘁 𝗠𝗮𝗸𝗲𝘀 𝗖𝗹𝗼𝘂𝗱𝗯𝗲𝗱𝘀 𝗨𝗻𝗶𝗾𝘂𝗲

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 𝗚𝗹𝗼𝗯𝗮𝗹 𝗗𝗶𝗿𝗲𝗰𝘁𝗼𝗿, 𝗠𝗶𝗱-𝗠𝗮𝗿𝗸𝗲𝘁 𝗢𝗻𝗯𝗼𝗮𝗿𝗱𝗶𝗻𝗴, you will own and scale the onboarding function for Cloudbeds' fastest-growing and most complex customer segment. You'll lead the team responsible for guiding mid-market customers from contract signature through go-live, adoption, and a clean transition to Account Management. You'll build the frameworks, standards, metrics, and team capability that make that experience world-class and repeatable at scale.

You'll inherit a team of dedicated ICs and leads that have been experimenting with new ways to support these customers and improve their experience. Your charter is to get leadership in place and be maniacal about customer experience while building the project-management rigor that complex mid-market deployments demand. You'll be measured on onboarding velocity, deployment quality, customer satisfaction, and the long-term retention impact of a strong start.


𝗢𝘂𝗿 𝗢𝗻𝗯𝗼𝗮𝗿𝗱𝗶𝗻𝗴 𝗧𝗲𝗮𝗺:

Our team is passionate about delivering exceptional customer experiences and helping hoteliers succeed with Cloudbeds from day one. We build together with a test-and-learn mindset that encourages innovation, collaboration, and continuous improvement. Every team member is valued and empowered to share feedback, ideas, and insights so we can learn, grow, and improve both as individuals and as a team. Leaders who thrive here are proactive communicators, collaborative problem-solvers, and true customer advocates who enjoy navigating complexity while building the systems and people that scale it.


𝗪𝗵𝗮𝘁 𝗬𝗼𝘂 𝗕𝗿𝗶𝗻𝗴 𝘁𝗼 𝘁𝗵𝗲 𝗧𝗲𝗮𝗺:

  • Lead, coach, and develop the Mid-Market Onboarding team — including Onboarding Project Managers and senior coaches — setting clear expectations, performance standards, growth paths, and a culture of accountability and continuous improvement
  • Own end-to-end onboarding outcomes for mid-market customers from sales handoff through go-live, adoption, and transition to Account Management — diagnosing and fixing execution gaps in training quality, error detection, and deployment velocity
  • Build standardized onboarding frameworks, SOPs, and configuration standards for complex multi-property and 25–100+ room deployments that balance customization with scalability
  • Establish and own the metrics that matter: onboarding velocity, deployment quality scores, training completion, CSAT/NPS, and early-lifecycle retention — monitoring portfolio health and intervening early on at-risk projects
  • Own capacity and staffing planning for the division — forecasting demand, balancing workload across the team, and partnering with leadership on headcount decisions
  • Serve as a senior escalation point for complex or at-risk mid-market deployments and partner with Account Management on clean, trust-preserving handoffs
  • Partner cross-functionally with Sales, Product, Support, Professional Services, and Account Management — bridging what gets sold and what gets delivered, and contributing to the broader strategy for how Cloudbeds serves mid-market and enterprise-adjacent customers

𝗪𝗵𝗮𝘁 𝗦𝗲𝘁𝘀 𝗬𝗼𝘂 𝗨𝗽 𝗳𝗼𝗿 𝗦𝘂𝗰𝗰𝗲𝘀𝘀:

  • 7+ years in hospitality or hospitality technology, including hands-on customer onboarding or implementation experience and team leadership (time at a hotel, hotel group, or a PMS or hospitality-tech company; OTA or travel-distribution experience on its own does not count)
  • Track record of building or significantly improving onboarding and implementation functions and frameworks
  • Proven people-leadership experience — hiring, coaching, and developing customer-facing teams in a distributed, global environment
  • Strong project-management foundation: scope, milestones, timelines, and risk mitigation applied to complex multi-stakeholder deployments
  • Deep understanding of hotel operations and the complexity of serving multi-property, mid-market hospitality customers
  • Ability to move fluidly between strategy and execution — you can design the framework and roll up your sleeves to implement it
  • Data-driven: comfortable with KPIs, dashboards, and using insights to drive decisions

𝗕𝗼𝗻𝘂𝘀 𝗦𝗸𝗶𝗹𝗹𝘀 𝘁𝗼 𝗦𝘁𝗮𝗻𝗱 𝗢𝘂𝘁:

  • Additional language fluency (Spanish, Portuguese) at a business-professional level
  • Direct experience onboarding or implementing customers at a hospitality SaaS or PMS company
  • Familiarity with property management systems, payments, or hospitality fintech
  • Experience building onboarding or implementation functions at a scale-up stage company
  • Background working with hotel management companies, small chains, or the consultant ecosystem

𝗖𝗼𝗺𝗽𝗲𝗻𝘀𝗮𝘁𝗶𝗼𝗻:

Depending on your skills and experience, you can expect your annual compensation to be between $𝟭𝟲𝟬,𝟬𝟬𝟬 𝗮𝗻𝗱 $𝟭𝟵𝟬,𝟬𝟬𝟬 𝗨𝗦𝗗. Please note that we maintain high flexibility, and packages above this range will be considered. (The salary is only for US-based candidates).

#LI-SD1


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


𝗖𝗹𝗼𝘂𝗱𝗯𝗲𝗱𝘀 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 [email protected]. 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.

#LI-REMOTE

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