[Hiring] Senior Customer Operations Lead @Breezeway

Role Description

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.

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.

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.

What You'll Do

• Own and optimize the customer experience — from onboarding through expansion and renewal.
• Define the requirements for lifecycle programs across HubSpot and in-app messaging (Appcues).
• Map, document, and continuously improve core customer processes end to end.
• Manage and evolve our customer operations infrastructure in HubSpot.
• Stand up repeatable, centralized dashboards in Metabase.
• Partner closely and stay tightly aligned with the Revenue Operations leader.
• Coordinate with Product Marketing on operating mechanisms and systems enablement.
• Collaborate with Sales on handoff quality, early lifecycle health, and expansion pipeline.
• Develop differentiated journey tracks for our B2C segment and upmarket B2B accounts.
• Build scalable playbooks for onboarding, check-ins, expansion, and churn risk.
• Leverage AI tools to standardize and automate repetitive Customer Success communications.
• Translate voice-of-customer and operational data back into product and process improvements.

Qualifications

• 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: building centralized dashboards, writing SQL queries, running 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 design end-to-end journey and process architecture.
• Strong written communication skills.
• Available and collaborative during Eastern Time hours.
• Early adopter of AI tools and an interest in experimenting with them.

Bonus Points

• Experience at a SaaS company serving the short-term rental, property management, or vacation rental market.
• 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

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

Company Description

Breezeway is an equal opportunity employer and prohibits discrimination based on race, color, religion, sex, national origin, age, disability, genetic information, or any other protected status. We embrace diversity and are committed to creating an inclusive workplace.

We're a remote-first company with team members across the U.S. and globe, but we currently hire only in the following states and countries:

• Countries: US and Spain
• United States: Arizona, Arkansas, California, Connecticut, Florida, Georgia, Idaho, Illinois, Maine, Massachusetts, Michigan, Missouri, Nevada, New Hampshire, New Jersey, New York, North Carolina, Ohio, Oregon, Pennsylvania, Rhode Island, South Carolina, Tennessee, Texas, Utah, Vermont, Virginia, Washington, and Wisconsin.