Breezeway - Senior Customer Operations Lead
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 • 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 • Tool You'll Use • Tool You'll Use • HubSpot · Metabase · Appcues · Claude · Granola · Slack · Gmail
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
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