VP, Customer Experience at Breezeway

Breezeway’s award-winning property operations and experience platform helps coordinate, communicate, and verify detailed work at properties. Powering over 55M property care tasks, Breezeway helps thousands of short-term rental managers and hospitality operators increase operational efficiency and boost service revenue while eliminating manual work and elevating the experience at each property. We are seeking an experienced and strategic VP, Customer Experience to lead Breezeway’s post-sale organization, including Customer Success, Implementation, Support, and Assist. This role is a key member of Breezeway’s leadership team, responsible for shaping company strategy through the lens of the customer. You will own the end-to-end customer lifecycle, with a focus on driving retention, improving operational efficiency, and building a scalable, high-performing CX organization. This leader will play a critical role in evolving how we deliver value to customers as we scale, balancing growth with efficiency, and ensuring strong unit economics alongside a best-in-class customer experience. This is a hands-on leadership role for someone who has successfully led CX functions in a B2B SaaS environment and has experience navigating organizational scale, process maturity, and change management. What You’ll Own Customer Experience Strategy • Define and lead Breezeway’s end-to-end post-sale strategy across onboarding, adoption, retention, and support • Establish clear KPIs and performance frameworks tied to retention, efficiency, and customer outcomes • Serve as the executive voice of the customer and bring customer insights into leadership discussions and company priorities • Ensure a consistent, high-quality customer experience across all touchpoints Team Leadership & Organizational Scale • Lead and develop a multi-layered CX organization, including senior leaders across Customer Success, Implementation, and Support • Evolve organizational structure, roles, and coverage models to support scale and profitability • Drive a high-performance culture grounded in accountability, clarity, and continuous improvement Customer Success & Retention • Own net revenue retention (NRR), gross retention, and overall customer health metrics • Build and scale programs that drive adoption, engagement, and long-term value realization • Partner closely with Sales to ensure seamless handoffs and aligned expectations across the customer lifecycle • Engage directly with strategic accounts and high-impact customer situations Implementation & Time-to-Value • Optimize onboarding processes to reduce time-to-value and improve activation rates • Standardize and scale implementation while maintaining flexibility across customer segments • Improve predictability and efficiency in onboarding delivery Support & Assist Operations • Oversee global support operations with a focus on responsiveness, quality, and cost efficiency • Implement scalable support models, including tiering, self-service, and escalation management • Leverage AI, automation, and tooling to improve support outcomes and team productivity • Ensure Assist functions are well-integrated and delivering measurable customer value Cross-Functional Leadership • Act as a core partner to Product, Sales, Marketing, and Finance to align on company priorities and execution • Partner with Product to incorporate customer insights into roadmap and prioritization • Collaborate with Sales and Marketing to ensure alignment across the full customer lifecycle • Work with Finance on forecasting, capacity planning, and improving overall unit economics Operational Excellence & Profitability • Build scalable processes, systems, and reporting across the CX organization • Drive efficiency improvements across onboarding, support, and customer success delivery • Establish capacity models and resource planning aligned with growth and margin targets • Leverage data, systems (including HubSpot), and AI to increase visibility and improve decision-making What We’re Looking For • 10–15+ years of progressive experience in Customer Experience or Customer Success leadership within B2B SaaS, including ownership of the full post-sale lifecycle (Success, Support, and Implementation) • Experience as the top CX leader at a ~$20M–$100M ARR company, or a senior leader owning a comparable segment within a larger SaaS organization • Track record of scaling CX through growth, including evolving org structure, processes, and operating rigor • Demonstrated success improving NRR, retention, onboarding efficiency, and cost-to-serve, with a clear understanding of CX’s impact on profitability • Experience in high-velocity SMB to mid-market environments with a focus on scalable, repeatable motions • Strong operator comfortable in the details—metrics, forecasting, capacity planning, and systems (HubSpot preferred) • Experience leading through change, including introducing new processes and performance expectations • Track record of building and developing strong CX teams, including hiring and coaching senior leaders • Comfortable engaging directly with customers in high-impact moments, including strategic accounts and escalations • Strong cross-functional partner to Product, Sales, Marketing, and Finance • Pragmatic, low-ego leader with a high ownership mindset Breezeway is an equal opportunity employer and prohibits discrimination based on race, color, religion, sex, national origin, age, disability, genetic information, or any other protected status. We embrace diversity and are committed to creating an inclusive workplace. We believe that respect fosters open-mindedness and curiosity, enabling us to gain valuable perspectives from our teammates, the market, and our clients. All qualified applicants will receive consideration for employment without regard to these factors. If you need accommodation during the application process, please let us know. We're a remote-first company with team members across the U.S. and globe, but we currently hire only in the following states and countries. Countries: US and Spain United States: Arizona, Arkansas, California, Connecticut, Florida, Georgia, Idaho, Illinois, Maine, Massachusetts, Michigan, Missouri, Nevada, New Hampshire, New Jersey, New York, North Carolina, Ohio, Oregon, Pennsylvania, Rhode Island, South Carolina, Tennessee, Texas, Utah, Vermont, Virginia, Washington, and Wisconsin.