Director of Customer Success Management - 100% Remote - North America

NOTE: This is a FULLY remote role, but the candidate must be within North American Central Standard Time or Eastern Standard Time to collaborate with their team, peers, and internal customers.

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.

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

We are looking for a Director of Customer Success Management who can take full ownership of our customer success organization and lead it into its next phase of growth. This is a hands-on, roll-up-your-sleeves role — not a position for someone who wants to sit in an ivory tower. You will be on the front lines with customers, while also evolving the strategy, structure, and playbooks that allow the department to scale.

The ideal candidate has experience building or being part of a high-growth SaaS customer success function, thrives in fast-paced startup environments, and knows how to balance strategic leadership with tactical execution. You’ll own the performance of our customer base, build strong client relationships, and help define how we leverage AI to scale customer success.

What You’ll Do

• Take full ownership of the Customer Success Management function — evolving its strategy, playbooks, and KPIs.

• Lead from the front: engage directly with key customers while coaching and developing the team.

• Drive accountability for core metrics like GRR, NRR, NPS, and renewal/expansion performance.

• Build and maintain executive-level relationships with clients, ensuring alignment on business outcomes.

• Partner with sales and leadership on commercial conversations, renewals, and upsell opportunities.

• Champion the use of AI-driven tools and processes to improve efficiency and scale the CS function.

• Represent the voice of the customer internally, influencing product, support, and operations.

• Travel as needed to meet clients 1:1 across all regions.

Requirements

• Proven track record as a Customer Success leader in a high-growth SaaS startup focusing on retention and churn reduction.

• Experience working with reactive retention manager style ICs in lower segments.

• Experience building or scaling a Customer Success function from the ground up.

• Hands-on leadership style — willing to be in the trenches with clients and the team.

• Strong commercial acumen with the ability to lead renewal and expansion discussions.

• Deep understanding of Customer Success KPIs (GRR, NRR, NPS) and how to move them.

• Excellent relationship-building and communication skills; able to quickly establish trust with clients.

• Comfortable operating with autonomy and accountability — takes direction but executes independently.

• Excited about the impact of AI on Customer Success and able to articulate its applications.

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 succes