Breezeway - VP, Customer Experience

• 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 • 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