Director of Customer Success & Onboarding - North America

Role overview Lead both customer onboarding and customer success for the North American region of a hospitality technology platform, owning everything from contract signature through multi-year renewals. You will design the regional operating model, grow a leadership team, and personally step in on the largest rollouts and most strategic accounts. The mandate includes revenue accountability through Net Revenue Retention while embedding AI-powered tooling into the daily workflow.

Responsibilities - Build and run a scalable customer success motion across the NA portfolio, including segmentation, coverage models, playbooks, and escalation paths suited to both independent properties and large hospitality operators. - Own Net Revenue Retention for the region, including renewals, expansion, and contraction, and hold the team accountable to engagement, health, and revenue outcomes. - Own onboarding and implementation end to end, from signed contract through go-live, setting resourcing, quality standards, and the regional operating model. - Define team structure, hiring, and roles as the NA business scales, and shape the regional customer experience strategy, priorities, headcount, metrics, and investment plan. - Shape how AI-powered capabilities (such as health scoring and automated risk flags) get built into onboarding and success operations and turn them into day-to-day practice. - Partner with regional commercial leadership, product, support, and channel and technology partners to close the loop on handoffs and joint implementations.

Requirements - 7 to 12+ years of post-sale leadership experience in SaaS, spanning customer success and onboarding in a single remit. - Track record of building and leading sizable CS and onboarding teams, including developing managers and senior individual contributors. - Hands-on experience leading complex, large-scale implementations with many internal and external stakeholders. - Proven ownership of a revenue number (NRR, GRR, or expansion), with fluency in the levers that move it. - Strong senior internal presence, including the ability to build a business case and influence without relying on formal authority. - AI fluency at an advanced level, with practical experience building an AI-powered tool or system rather than only adopting one. - Based in Arizona, Colorado, Connecticut, Florida, Georgia, Illinois, Kansas, Massachusetts, Montana, Nevada, New Jersey, New York, North Carolina, Ohio, South Carolina, Tennessee, Texas, Utah, Vermont, Virginia, or Wisconsin, with willingness to travel within North America.

Nice to have - Background in hospitality technology or hospitality operations, with working knowledge of PMS workflows and how hotels actually run. - Experience in a high-growth, international SaaS environment where you had to build the playbook rather than inherit one.

Benefits and work setup - Remote-first culture with hybrid flexibility, work-from-anywhere policy, and relocation options available after one year. - Home office setup budget plus a monthly work-from-home allowance, and access to AI productivity tokens for workflow automation. - Local benefits vary by location, including healthcare, retirement plans, and team events; salary band shared during the hiring process.