Director of Onboarding - 100% Remote - North America

NOTE: This is a FULLY remote role, but the candidate must be within the United States to collaborate with their team, peers, and internal customers. You do not have to be in the specific country or city shown in this listing, but please only apply if you are physically based within the United States.

Hostaway is a SaaS scale-up that is transforming the vacation rental industry. With innovative solutions and partnerships with giants like Airbnb, VRBO, and Booking, we're taking on the competition and winning. Leveraging our customer-centric core values, we consistently deliver results that encourage growth, learning, and innovation for our team, our customers, and the industry.

Exciting news: Hostaway has officially reached unicorn status! Wondering what that means? It’s a rare milestone in the startup world—our company is now valued at over $1 billion! We’ve raised an incredible $550M in the past 18 months, fueling our rapid growth and innovation. There’s never been a more thrilling time to join us - find out more here!

About the role

The Director of Customer Onboarding owns the vision, effectiveness, and growth of Hostaway’s global onboarding organization. This leader ensures every customer—from small operators to large hospitality groups—experiences a seamless journey from signed contract to full activation, driving rapid time-to-value and long-term success.

A key priority of the role is building a high-performing onboarding team and elevating operational excellence across the department. This includes hiring, developing, and scaling a strong enterprise onboarding function, designed to support strategic, high-touch customers with complex implementations.

The Director works cross-functionally with Sales, Product, Technical Support, and Customer Success to ensure smooth handoffs, predictable go-live timelines, consistent delivery quality, and high customer satisfaction.

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.

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

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

• Experience establishing or growing an enterprise or high-touch onboarding function.

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

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

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

• Ability to engage senior stakeholders.

• Strategic leader with hands-on operational execution strength.

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

What we offer

• Competitive Compensation: We offer competitive pay based on market rates in the country of the applicant.

• 100% Remote: Enjoy the freedom to work from anywhere within your country of residence—be it a co-working space, your home office, or even your dining room table. The choice is yours. Just don’t ask to work in our office (we don’t have one).

• Equity: Every role in our company comes with valuable stock options in a fast-growing and profitable company. This ensures we all share in the company’s success.

• Values-Driven Leadership: Our Core Values are not just words we’ve written to make us feel good. We leverage them daily when making strategic and tactical decisions.

• Professional Growth: Our rapid growth offers unparalleled learning and development opportunities, along with a multitude of career advancement opportunities.

• 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. The specifics depend on the country of the applicant.

• Dynamic Team Culture: As a global company with team members in over 40 countries, our diverse and international culture fuels our innovation and creativity, providing a key pillar to our success (and making it a lot of fun to work here).

Thank you for your interest. If you apply for this role, you will receive an email from our Talent Acquisition team after your application has been reviewed alongside the qualifications for this role and the qualifications of others who have applied.