VP, Customer Experience

Breezeway

2d•Remote

About The Position

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.

Requirements

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

Responsibilities

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
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
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
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
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
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
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