Pasito (YC S22) - QA Engineer

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.

The Role

We’re looking for a Senior QA Engineer to elevate product quality across Pasito’s AI‑native platform.

This is not a traditional checkbox‑driven QA role. You’ll be testing AI‑assisted tools that support complex, high‑stakes workflows in a regulated industry. Your job is to help the team understand how the system behaves end‑to‑end, surface risk early, and ensure we ship software our customers can trust.

As an early quality team member, you’ll help define what “quality” means at Pasito—balancing speed with rigor, automation with human judgment, and innovation with reliability.

What You’ll Do

Own testing for our document product: Take ownership of quality for certain Pasito product experiences, testing critical, high-impact flows used by insurance carriers and partners where accuracy, trust, and correctness are non-negotiable.

Test AI‑assisted tools: Design and execute test strategies for Pasito AI workflows,where you’ll validate correctness, reliability, edge cases, and failure modes in systems where outputs may vary and nuance matters.

Write end-to-end (E2E) tests and setup a reliable testing environment: Design and maintain robust E2E test coverage for core user journeys, ensuring confidence across releases and helping the team move quickly without sacrificing reliability.

Balance manual and automated testing: Apply a thoughtful mix of exploratory, manual, and automated testing. You’ll know when automation adds leverage—and when careful human evaluation is essential to real quality.

Own quality signals, not just test cases: Test across data flows, backend logic, and frontend experiences. You’ll help the team understand risk by validating how systems behave end‑to‑end, especially in data‑dense and workflow‑heavy scenarios.

Collaborate as part of the team: Work closely with engineers, product managers, designers, and non‑technical teammates. You’ll raise concerns early, contribute ideas, and help evolve how quality is defined, measured, and communicated across the company.

Partner with Forward Deployed team: Work closely with the Forward Deployed team to QA specific client portals, ensuring product quality meets the unique and non-negotiable needs of our most strategic clients.

Who You Are

A Quality Assurance professional with 4+ years of experience testing complex software systems.

Highly fluent in QA fundamentals: test design, exploratory testing, regression strategies, and release confidence

Comfortable testing AI‑assisted systems, with an understanding that AI outputs are probabilistic and require nuanced validation

Technically curious and hands‑on, able to reason about how systems work beyond the UI layer

Collaborative, communicative, and pragmatic—you optimize for real product quality, not theoretical perfection

Technical Experience We’re Excited About

Strong experience working with CI/CD pipelines, test planning, test reporting, and maintaining quality in fast‑paced environments

Solid experience with test automation tools, particularly Playwright

Hands‑on exposure to AI or LLM‑powered tools (either as a tester or builder)

Experience in insurance, healthcare, or financial services is a plus—but not required

What’s In It For You

Meaningful ownership: Define and lead quality for a mission‑critical AI product used by carriers, brokers, employers, and employees

Real impact: Your work directly affects trust, accuracy, and adoption in a system people depend on every day

Growth: Join early and grow with the company as we scale product, team, and distribution

Competitive compensation: Salary, meaningful equity, and benefits

Remote‑first: Work remotely with a highly collaborative team

Statement of Equal Opportunity

We are a company that values diversity and appreciates the benefits a diverse workforce

produces for our team and clients. We welcome all qualified applicants to apply.