Enterprise Onboarding Specialist - 100% Remote - North America

Confidential

Remote job permanent

Posted: April 8, 2026

Job Description

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.

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