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Enterprise Onboarding Specialist - 100% Remote - North America

May 9, 2026

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.

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 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.

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Common Interview Questions And Answers

1. HOW DO YOU PLAN YOUR DAY?

This is what this question poses: When do you focus and start working seriously? What are the hours you work optimally? Are you a night owl? A morning bird? Remote teams can be made up of people working on different shifts and around the world, so you won't necessarily be stuck in the 9-5 schedule if it's not for you...

2. HOW DO YOU USE THE DIFFERENT COMMUNICATION TOOLS IN DIFFERENT SITUATIONS?

When you're working on a remote team, there's no way to chat in the hallway between meetings or catch up on the latest project during an office carpool. Therefore, virtual communication will be absolutely essential to get your work done...

3. WHAT IS "WORKING REMOTE" REALLY FOR YOU?

Many people want to work remotely because of the flexibility it allows. You can work anywhere and at any time of the day...

4. WHAT DO YOU NEED IN YOUR PHYSICAL WORKSPACE TO SUCCEED IN YOUR WORK?

With this question, companies are looking to see what equipment they may need to provide you with and to verify how aware you are of what remote working could mean for you physically and logistically...

5. HOW DO YOU PROCESS INFORMATION?

Several years ago, I was working in a team to plan a big event. My supervisor made us all work as a team before the big day. One of our activities has been to find out how each of us processes information...

6. HOW DO YOU MANAGE THE CALENDAR AND THE PROGRAM? WHICH APPLICATIONS / SYSTEM DO YOU USE?

Or you may receive even more specific questions, such as: What's on your calendar? Do you plan blocks of time to do certain types of work? Do you have an open calendar that everyone can see?...

7. HOW DO YOU ORGANIZE FILES, LINKS, AND TABS ON YOUR COMPUTER?

Just like your schedule, how you track files and other information is very important. After all, everything is digital!...

8. HOW TO PRIORITIZE WORK?

The day I watched Marie Forleo's film separating the important from the urgent, my life changed. Not all remote jobs start fast, but most of them are...

9. HOW DO YOU PREPARE FOR A MEETING AND PREPARE A MEETING? WHAT DO YOU SEE HAPPENING DURING THE MEETING?

Just as communication is essential when working remotely, so is organization. Because you won't have those opportunities in the elevator or a casual conversation in the lunchroom, you should take advantage of the little time you have in a video or phone conference...

10. HOW DO YOU USE TECHNOLOGY ON A DAILY BASIS, IN YOUR WORK AND FOR YOUR PLEASURE?

This is a great question because it shows your comfort level with technology, which is very important for a remote worker because you will be working with technology over time...