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