Senior Customer Operations Lead

Breezeway

8d • 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'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.

Requirements

• 4–7 years in customer operations, revenue operations, customer success operations, or a closely related role — with clear ownership of customer journey programs and operational analytics
• Proven track record in a high-velocity startup or scale-up environment; you know how to build and ship while the plane is flying
• Strong HubSpot expertise — workflows, sequences, pipeline management, health scoring, and reporting — you can own this tool, not just use it
• Strong quantitative skills: you can build centralized dashboards in Metabase (or equivalent), write SQL queries, run cohort and funnel analysis, model a forecast, and surface the insight the business actually needs — without waiting on a data team
• Experience with pipeline management and forecasting — you understand how customer health data connects to revenue projections and can partner with Rev Ops to build and maintain that model
• Experience working cross-functionally with Revenue Operations, Customer Marketing, and Product Marketing — you know how to set clear requirements, align on shared metrics, and manage handoffs between teams
• Primary experience owning B2C customer journeys, with meaningful exposure to B2B or upmarket accounts — you understand what changes and what doesn't across segments
• A systems and process thinker who can zoom out to design end-to-end journey and process architecture and zoom in to QA the automation detail
• Strong written communication — you can write clear journey requirements for Customer Marketing, a CS playbook, and a sharp internal data brief with equal clarity
• Available and collaborative during Eastern Time hours; comfortable working with distributed teammates across time zones
• Early adopter of AI tools and an interest in experimenting with them to scale your own work

Nice To Haves

• Experience at a SaaS company serving the short-term rental (STR), property management, or vacation rental market — you understand the software layer these operators rely on, not just the industry itself
• Familiarity with vertical SaaS, operations platforms, or field service software
• Background in product-led growth (PLG) motions and self-serve onboarding design
• Hands-on experience with Appcues or similar in-app engagement platforms

Responsibilities

• 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, who owns the messaging, content, and build of customer-facing emails and in-app experiences. Jointly own success metrics, measure performance, and iterate to drive activation, retention, and revenue growth
• 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 — and maintain them as the business evolves
• Partner closely and stay tightly aligned with the Revenue Operations leader as we scale our commercial and go-to-market motion — on pipeline management, forecasting models, and the data infrastructure that ties customer outcomes to revenue outcomes
• Coordinate with Product Marketing on operating mechanisms and systems enablement - go to market readiness for the CX teams, including the systems updates, training and materials that keep Implementation, Support, and CS current
• 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, with the right depth of touch and analytics for each
• 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 across the customer segments and tiers, as well as scale personalized outreach without sacrificing quality
• Translate voice-of-customer and operational data back into product and process improvements — serving as a connective tissue role across the revenue org

Benefits

• equal opportunity employer
• prohibits discrimination based on race, color, religion, sex, national origin, age, disability, genetic information, or any other protected status
• embrace diversity and are committed to creating an inclusive workplace
• 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
• remote-first company with team members across the U.S. and globe

What This Job Offers

• Job Type: Full-time
• Career Level: Senior
• Education Level: No Education Listed