Senior Customer Operations Lead - 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're hiring a Senior Customer Operations & Customer Journey Lead to own the end-to-end post-sale experience. This is a high-impact, hands-on role for someone who lives at the intersection of data, process design, and customer empathy — someone who can build a quantitative model in the morning and redesign a new, optimized end-to-end process in the afternoon.

You'll design and run the journeys that turn activated users into power users and power users into advocates. You'll own our customer operations infrastructure, build the analytical foundation that drives decisions, and partner closely with Sales, Customer Success, Product, and Marketing to ensure customers are succeeding at every stage — whether they're small independent property owners or enterprise-scale property managers/operators.

In addition to being a strategic thought partner with the SVP of Client Experience, there are three key partnerships central to this role. You'll work in close alignment with our Revenue Operations leader as we scale our commercial and go-to-market motion. You'll define the customer journey requirements — audiences, triggers, timing, and success metrics — in partnership with the Customer Marketing Manager who will write and execute against in service to scaling and optimizing how we serve our customers. And you'll coordinate with Product Marketing on the operating mechanisms and enablement that keep CX teams ready for every launch and change.

This role is quantitative and process-driven at its core. You're not just designing journeys — you're measuring them rigorously, mapping and improving the processes behind them end to end, building the dashboards that give every team a shared view of pipeline health and customer outcomes, and translating that data into forecasts and recommendations that leadership can act on.

What You'll Do

• Own and optimize the customer experience — from onboarding through expansion and renewal — using quantitative customer data, supported by qualitative signals, to identify friction, opportunity, and risk
• Define the requirements for lifecycle programs across HubSpot and in-app messaging (Appcues) — audiences, triggers, timing, and enrollment logic — in partnership with the Customer Marketing Manager
• Map, document, and continuously improve core customer processes end to end — handoffs, owners, SLAs, and controls — so they scale as the business grows
• Manage and evolve our customer operations infrastructure in HubSpot: workflows, pipelines, health scoring, segmentation, and reporting
• Stand up repeatable, centralized dashboards in Metabase that give CS, Sales, Rev Ops, and leadership a single shared view of customer health, journey-stage performance, and revenue trends
• Partner closely and stay tightly aligned with the Revenue Operations leader as we scale our commercial and go-to-market motion
• Coordinate with Product Marketing on operating mechanisms and systems enablement - go to market readiness for the CX teams
• Collaborate with Sales on handoff quality, early lifecycle health, and expansion pipeline — ensuring alignment between pre- and post-sale motion
• Develop differentiated journey tracks for our B2C segment (independent property managers) and our upmarket B2B accounts
• Build scalable playbooks for onboarding, check-ins, expansion, and churn risk — and train the CS team to run them
• Leverage AI tools, including Claude, to standardize and automate repetitive Customer Success 1:1 communications
• Translate voice-of-customer and operational data back into product and process improvements

What We're Looking For

• 4–7 years in customer operations, revenue operations, customer success operations, or a closely related role
• Proven track record in a high-velocity startup or scale-up environment
• Strong HubSpot expertise — workflows, sequences, pipeline management, health scoring, and reporting
• Strong quantitative skills: build centralized dashboards in Metabase, write SQL queries, run cohort and funnel analysis
• Experience with pipeline management and forecasting
• Experience working cross-functionally with Revenue Operations, Customer Marketing, and Product Marketing
• Primary experience owning B2C customer journeys, with meaningful exposure to B2B or upmarket accounts
• A systems and process thinker who can zoom out to design architecture and zoom in to QA automation details
• Strong written communication skills
• Available and collaborative during Eastern Time hours; comfortable working with distributed teammates
• Early adopter of AI tools with an interest in experimenting to scale your work

Tools You'll Use

• HubSpot · Metabase · Appcues · Claude · Granola · Slack · Gmail