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Hostaway · 17 hours ago

Director of Onboarding - 100% Remote - North America

United States

Contract

Remote

Director/Executive

7+ years exp

Hostaway is a SaaS scale-up transforming the vacation rental industry. The Director of Customer Onboarding is responsible for leading the global onboarding organization, ensuring a seamless journey for customers from contract signing to activation, while building a high-performing team and enhancing operational excellence.

Property ManagementSoftwareVacation Rental

Growth Opportunities

Responsibilities

Lead and develop the global Customer Onboarding team, setting success metrics, training, and scalable methodologies

Build and scale an Enterprise Onboarding team for complex, high-value accounts, ensuring timely, high-quality implementations

Collaborate cross-functionally with Sales, Product, Engineering, Customer Success, and Support to ensure smooth onboarding and transitions

Oversee onboarding projects, integrations, and escalations, driving accountability for timelines and customer outcomes

Ensure excellent onboarding experiences, strong activation, and high satisfaction across all customer segments

Design and optimize scalable processes, analyze data to improve onboarding, and partner on reporting, automation, and resource planning

Qualification

Customer OnboardingSaaS ExperienceTeam LeadershipAI for AutomationProcess OptimizationSalesforceHubSpotGongZendeskJiraStakeholder EngagementData-DrivenOperational Execution

Required

7–10+ years in Customer Onboarding, Implementation, or Professional Services, including 3–5+ years leading global teams

Proven experience designing and driving a new operating model

Experience directly leading teams in a remote and global perspective

Proven success scaling a customer onboarding or services team in a SaaS environment

Proven experience using AI for Automation

Background in large-scale, multi-stakeholder system implementations and integrations

Ability to engage senior stakeholders

Strategic leader with hands-on operational execution strength

Data-driven, process-oriented, and passionate about continuous improvement

Preferred

Experience in short-term rental, hospitality tech, PMS, or travel/tourism strongly preferred

Familiarity with Salesforce, HubSpot, Gong, Zendesk, Jira, or similar platforms

Benefits

Equity: Every role in our company comes with valuable stock options in a fast-growing and profitable company.

Annual Paid Leave: The specific amounts vary by country and are aligned with country and/or contract-specific norms.

Geographic Specific Benefits: As an international employer, we offer different country-specific benefits such as Health Insurance and Pensions in countries where these perks are customary.