Senior Customer Operations Lead

About the Opportunity
The organization is seeking a Senior Customer Operations Lead to own the end-to-end post-sale experience. This hands-on, quantitative role bridges data analysis, process design, and customer experience to transform activated users into power users and advocates.
In this role, you will oversee customer operations infrastructure, establish the analytical foundation that drives strategic decisions, and collaborate cross-functionally with Sales, Customer Success, Product, and Marketing to support customers ranging from independent operators to enterprise accounts. You will serve as a strategic thought partner to executive leadership in client experience, align closely with Revenue Operations on commercial go-to-market motions, collaborate with Customer Marketing to define journey requirements, and coordinate with Product Marketing on enablement and operating mechanisms.
Key Responsibilities
Own and optimize the customer experience across onboarding, expansion, and renewal using quantitative data and qualitative signals to pinpoint friction, opportunities, and churn risk.
Define lifecycle program requirements across HubSpot and in-app messaging (Appcues), establishing audiences, triggers, timing, and enrollment logic in partnership with Customer Marketing, while jointly tracking performance metrics to drive activation and retention.
Map, document, and continually refine core customer processes end to end, defining handoffs, ownership, service level agreements, and operational controls.
Administer and expand customer operations infrastructure within HubSpot, managing workflows, pipelines, customer health scoring, segmentation, and reporting.
Build and maintain centralized, repeatable dashboards in Metabase to give Customer Success, Sales, Revenue Operations, and leadership visibility into customer health, journey performance, and revenue trends.
Align closely with Revenue Operations on pipeline management, forecasting models, and data infrastructure linking customer outcomes to revenue.
Coordinate with Product Marketing to ensure operational readiness across Customer Experience teams, including system updates, training, and materials for Implementation, Support, and Customer Success.
Collaborate with Sales on handoff quality, early lifecycle health, and expansion pipelines to keep pre-sale and post-sale motions aligned.
Establish differentiated customer journey tracks tailored to consumer-scale independent operators and upmarket business accounts.
Develop and maintain scalable playbooks for onboarding, check-ins, expansion, and churn prevention, training Customer Success team members on execution.
Utilize AI tools, such as Claude, to standardize repetitive 1:1 customer communications, scale outreach, and maintain quality.
Channel voice-of-customer insights and operational findings back into product and operational enhancements.
Required Qualifications
4 to 7 years of experience in customer operations, revenue operations, customer success operations, or a closely related discipline, with demonstrated ownership of customer journey initiatives and operational analytics.
Proven track record operating in a high-velocity startup or scale-up environment.
Advanced expertise in HubSpot, including workflows, sequences, pipeline management, customer health scoring, and reporting.
Strong quantitative and analytical capabilities, including writing SQL queries, building centralized dashboards in Metabase (or an equivalent platform), conducting cohort and funnel analyses, and developing forecast models.
Practical experience with pipeline management and forecasting, with the ability to connect customer health metrics to revenue projections.
Experience working cross-functionally with Revenue Operations, Customer Marketing, and Product Marketing teams to define requirements, align on shared metrics, and manage team handoffs.
Primary experience leading B2C customer journeys alongside meaningful exposure to B2B or upmarket accounts.
Strong systems and process design orientation, capable of developing high-level journey architecture as well as auditing automation logic.
Strong written communication skills for creating journey specifications, playbooks, and internal analytical summaries.
Availability to collaborate during Eastern Time business hours and work effectively with distributed team members across time zones.
Demonstrated adoption of AI tools and an active interest in applying them to enhance workflows.
Preferred Qualifications
Experience working at a SaaS company serving the short-term rental, property management, or vacation rental sector.
Familiarity with vertical SaaS, operations software, or field service platforms.
Background supporting product-led growth (PLG) strategies and designing self-serve onboarding workflows.
Hands-on experience with Appcues or comparable in-app engagement tools.
Technology Environment
HubSpot
Metabase
Appcues
Claude
Granola
Slack
Google Workspace (Gmail)
Work Location and Schedule
Full time.
Remote-first position within the United States. Candidates must reside in one of the following eligible 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, or Wisconsin.
Core working hours require availability and active collaboration during Eastern Time hours.
Equal Opportunity and Accommodations
The hiring organization is an equal opportunity employer and prohibits discrimination on the basis of race, color, religion, sex, national origin, age, disability, genetic information, or any other protected status. All qualified applicants will receive consideration for employment. Accommodations are available for individuals who require assistance during the application process.

Work arrangement
Yes