Enterprise Onboarding Specialist - 100% Remote - North America

NOTE: This is a FULLY remote role, but the candidate must be within North America EST or CST time zones 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 North America EST or CST time zones. Trusted by 20,000+ property managers worldwide, Hostaway is an industry leading, AI-powered vacation rental management platform designed for professional short-term rental operators. Hostaway brings everything together for greater efficiency and faster growth.

• Profitable, high-growth, and the first short-term rental PMS unicorn . Join us at our most exciting stage yet! Learn more about our recent valuation and story here.
• About the role

As an Enterprise Onboarding Specialist, you will lead complex onboarding implementations for large and strategic customers. You will act as the primary implementation partner during onboarding, guiding customers through a structured milestone based rollout designed to support successful platform adoption and Onboarding completion. This role combines project management, customer consulting, stakeholder alignment, and solution enablement. You will collaborate closely with Sales, Customer Success, Product, and Technical teams to ensure Enterprise customers successfully transition onto the Hostaway platform.

• You will also travel occasionally to support onsite onboarding workshops, kickoff sessions, and implementation alignment meetings with strategic customers.
• Key responsibilities:
• Lead end-to-end onboarding implementations for Enterprise customers from kickoff through successful completion.
• Serve as the primary point of contact and trusted advisor for Enterprise stakeholders throughout onboarding.
• Build and execute milestone-based onboarding plans aligned to customer goals, timelines, technical requirements, and rollout strategy.
• Manage onboarding timelines, dependencies, risks, stakeholder expectations, and implementation visibility across systems such as Salesforce and Rocketlane.
• Align Hostaway capabilities to customer workflows and business objectives to drive successful adoption.
• Coordinate cross-functional implementation activities with Sales, Customer Success, Product, and Support teams.
• Deliver tailored onboarding workshops, training sessions, and solution walkthroughs for customer teams and leadership.
• Identify opportunities to improve onboarding processes and support onsite onboarding engagements when needed.
• Requirements
• 3 to 5+ years experience in SaaS onboarding, implementation, or project management roles supporting mid market or Enterprise customers
• Strong project management skills with experience coordinating multi-stakeholder implementations
• Experience working with complex customer environments and cross-functional decision makers
• Excellent communication, facilitation, and executive level presentation skills
• Ability to manage multiple concurrent onboarding implementations with competing priorities
• Strong problem-solving mindset and ability to navigate ambiguity in fast-growing environments
• Experience delivering structured onboarding or implementation frameworks
• Comfort working directly with technical and operational stakeholders
• Willingness to travel occasionally for onsite customer onboarding engagements
• 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 crea

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