Pasito (YC S22) - Data Analyst

About Pasito Pasito is the AI workspace for employee benefits. We’re rethinking how group insurance and benefits are underwritten, delivered, used and measured - by the people who design them and the people who depend on them. Instead of static PDFs, disconnected systems, and manual workflows, Pasito brings plan design, payroll and benefits data, claims, and financial context into a single, AI‑native workspace that helps benefits actually work for the 178 million Americans who depend on this system. We don’t build for brokers, carriers and employers - we build with them. That collaboration shows up in everything we ship: AI agents that extract and structure plan data, tools that turn complexity into clarity for employees, and workflows that save carriers and consultants hundreds of hours per case. Today, Pasito supports many of the largest insurance carriers and brokers in the U.S. We’re backed by Y Combinator and Core Innovation Capital, and we’re growing quickly. We ship fast, iterate relentlessly, and care deeply about building systems that are accurate, scalable, and human. If you’re excited to work alongside exceptional operators and engineers, and apply AI in a legacy industry where precision and trust matter, Pasito is the place for you. About the Role Pasito is hiring a Data Analyst who understands that data is most powerful when it drives decisions. You'll partner closely with our Data Engineer to design and build dashboards that translate complex data into clear, actionable insights for internal teams, client stakeholders, and executive sponsors. You'll own Pasito's ROI narrative and product analytics story — identifying the metrics that best demonstrate our product's impact, ensuring they hold up to scrutiny, and communicating them with the confidence and precision that earns trust at every level of an organization. What You'll Do Own the analytics narrative — identify, define, and continuously refine the metrics that best demonstrate Pasito's product value and ROI to external stakeholders. Lead product analytics — define how Pasito's product is described and understood through data, building the reporting framework that captures engagement, adoption, and outcomes in a way that is accurate, compelling, and tailored for each stakeholder. Design data dashboards in collaboration with our Data Engineer, translating business and product questions into intuitive, visually compelling reporting experiences. Partner cross-functionally with Product, Customer Success, Sales, and Leadership to understand what questions matter most and ensure the right data is surfaced at the right time. Prepare and deliver data presentations to internal senior leadership and external executive sponsors — communicating findings clearly, confidently, and without jargon. Enable others to present data effectively — coach and train internal team members on how to communicate data-driven insights with confidence, and prepare presentation-ready work that others can own and deliver when needed. Proactively explore data to uncover trends, anomalies, and opportunities that the business hasn't yet thought to ask about. Establish and maintain data definitions and reporting standards so that everyone is working from a single source of truth — including standardized language for how the product's performance is described internally and externally. Conduct competitive analysis — research the metrics and benchmarks that peer companies and competitors report on, evaluate their relevance to Pasito, and make informed recommendations about whether and how to adopt them into our reporting framework. Partner with Marketing to identify and maintain the top data points the sales team needs to effectively communicate Pasito's product value in the field — ensuring those numbers are current, accurate, and easy to use. Collaborate with the Partnerships team to surface data-driven insights that inform partner strategy — including identifying early risk indicators and establishing best practices based on performance trends across the portfolio. Define and track AI product metrics — develop the framework for measuring the performance and impact of Pasito's AI-driven features, identifying the indicators that best reflect the value those components deliver to users and stakeholders. Iterate continuously — test new approaches to data visualization and communication, gather feedback from stakeholders, and refine over time. Who You Are You take ownership of your work. You don't wait to be handed a question — you identify the questions worth answering and pursue them with rigor. You believe that good product analytics starts with genuine understanding — of the product, the people it serves, and the value it creates — and you let that understanding shape how you communicate through data. You're a strong cross-functional collaborator who can work effectively with technical and non-technical stakeholders alike, and bring people along even when they don't speak "data." You communicate with clarity and confidence. You can present complex findings to a senior executive audience and know how to frame data in terms that resonate at every level. You hold yourself to a high standard of accuracy and can defend your methodology when pressed. You're comfortable with ambiguity and able to prioritize in a fast-moving environment without losing attention to detail. You're a continuous learner who stays current on industry benchmarks, reporting trends, and evolving best practices in analytics. What We're Looking For 4–6 years of experience in a data analyst or similar role, ideally with a product analytics component Experience in insurance or a related industry, with an understanding of how value is defined and communicated differently across stakeholders — carriers, brokers, employers, and employees Strong proficiency in SQL; experience with BI tools such as Metabase, or similar Demonstrated ability to build dashboards and reports that are both technically rigorous and visually clear Experience defining and reporting on product metrics — engagement, adoption, outcomes — for varied audiences Experience translating business and product goals into data requirements and vice versa Comfortable presenting data-driven findings to senior and executive audiences Demonstrated ability to ramp quickly in a new domain and develop fluency in unfamiliar subject matter Nice to Have Experience at a B2B SaaS or benefits/HR tech company Familiarity with dbt or data modeling concepts Experience building external-facing client analytics or reporting products Background in financial wellness, healthcare, or employee benefits Experience working with or analyzing AI-powered products, including familiarity with how AI-driven outcomes are measured and communicated to stakeholders What’s In It For You Foundational ownership: Be the person who builds Pasito's data and analytics foundation from the ground up — establishing the metrics, systems, and reporting frameworks that will define how the company measures success post Series A. Strategic impact: Partner directly with Leadership on how data informs forecasting, product decisions, and go-to-market execution — your work will shape the decisions that matter most. Meaningful influence: Define how Sales, Marketing, and Partnerships understand and use data — and build the standards that drive long-term, scalable growth. Growth: Join at a pivotal stage and grow into a senior analytics leadership role as the company scales. We believe great teams are built through diversity of background, perspective, and experience, and we’re committed to creating an inclusive environment where everyone can do their best work. Interview Process Silver screening Interview Silver Technical Interview Client Screening Interview Take Home Take Home Pannel