Enterprise Customer Success Manager - 100% Remote - North America CST

NOTE: This is a FULLY remote role, but the candidate must be within North America CST areas to collaborate with their team, peers, and 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 CST areas.

Hostaway is the market-leading SaaS scale-up 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.

As a profitable and growing company, this role is necessitated by our continued growth. Check out more about our recent funding round of $365 million here.

About the role

We are seeking an experienced Enterprise Customer Success Manager (CSM) to join our team and manage our largest customers across the United States and Canada. This individual will own a defined book of business and act as a trusted advisor to enterprise accounts, driving adoption, retention, and growth.

The role requires a blend of strategic account management, commercial acumen, and the ability to get into the weeds with clients to deeply understand their business processes and how our solutions address their most critical pain points.

What you’ll do

• Manage relationships with our largest enterprise customers in the US and Canada, serving as their primary point of contact.

• Build deep customer partnerships by understanding clients’ business processes and demonstrating how our platform delivers value.

• Drive renewals and proactively manage the commercial health of your accounts, including forecasting upsells, downsells, and churn risk.

• Lead commercial conversations with confidence, identifying growth opportunities and negotiating terms to mutual success.

• Develop rapport and trust with executive and operational stakeholders by meeting clients in person and serving as a consultative partner.

• Own a defined book of business and maintain a strong command of customer-specific strategies, goals, and use cases.

• Identify additional solutions or integrations — both internal and external — that can help clients achieve their objectives.

• The ideal candidate will be an experienced enterprise CSM with strong commercial skills and a proven ability to manage high-value accounts.

• Prior experience as an Enterprise Customer Success Manager in a SaaS company.

• Demonstrated success driving renewals, expansions, and forecasting account health (upsells/downsells/churns).

• Proven ability to lead commercial conversations with executive stakeholders.

• Ability and willingness to travel across the US and Canada to meet customers in person.

• Strong relationship-building skills and ability to establish trust with clients across all levels of the organization.

• Adept at understanding complex business processes and mapping solutions to customer pain points.

• Knowledge of the short-term rental property management industry is a strong plus.

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.