Senior Test Automation Engineer (Python + Playwright), AI Healthcare

Long-term, full-time project. Individuals only. Linear Health builds AI that does the back office work US clinics can't keep up with: referrals, prior authorizations, scheduling, patient outreach, and voice agents that call and answer patients. Our customers are community health centers and specialty practices. We're bootstrapped and profitable. WHY THIS ROLE EXISTS Every customer runs their own deployment, with their own configuration, EHR and rules. That's good for them, but it means every release has to be proven against every customer. Today, people who know the product check releases by hand, and that won't take us from 10 customers to 100 customers. We'd rather build something smarter than hire a tester for every handful of customers. You're the person who builds it. WHAT YOU'LL BUILD • Production checks that ask yes or no questions every few minutes, across every customer. Did the referral reach a final state? Did the prior auth get a payer acknowledgement? Did the appointment the voice agent confirmed actually land in the EHR? • A config file for every customer, with a checker that proves the live deployment matches it • Our shared test framework in Python and Playwright, published as a versioned package every project installs • Workflow tests for every customer that run nightly and before each release, behind one command that comes back green or red • Test scenarios for our voice and chat agents, run against simulated patients • The standards our engineers and their AI coding tools follow, so every change ships with its own tests WHAT'S ALREADY IN PLACE • Security scanning on every repo, and pull request checks that block merges • Unit tests with every change • API contract tests generated from our OpenAPI spec • GitHub Actions running Playwright in parallel, with test results tied to every commit • A written quality strategy, automation plan and build standard that you'll own YOU'LL FIT IF YOU • Have 5+ years in test automation and have designed a framework other engineers depend on • Are strong in Python, Playwright and pytest • Know how to test workflows whose results arrive minutes later, without fixed sleeps • Have tested healthcare software, or AI and voice products • Can own a strategy on your own, explain it in plain English, and hold engineers to it • Use AI coding tools every day and know where they go wrong HOW WE WORK • Full time and exclusive. Individuals only, no agencies or teams, and no other clients once you start • Minimum 6 hours a day of overlap with US Central time, Monday to Friday • Synthetic data only. You'll never need real patient data, and you'll complete our HIPAA and security training before you start • Small, flat team. You own quality from day one HOW TO APPLY (PLEASE READ CAREFULLY) Start your proposal with the word "Gate". We automatically reject any proposal that uses em dashes (the long dash), so please write it yourself or edit it after AI writes it. Then record a Loom of no more than 2 minutes, with your camera on, answering the task below, and put the link in your proposal. Don't build anything. We want to hear how you think. THE TASK A clinic sends a referral through our API. We reply "accepted" straight away. Behind the scenes it moves to "processing", then anywhere from 30 seconds to 10 minutes later it becomes "confirmed" or "failed". "Confirmed" only counts if the referral really exists in the clinic's EHR. Imagine 30 customers, each set up differently. Test runs can never use real patient data, and must never send a real fax, text or call. In 2 minutes, tell us: 1. How you'd test this automatically on every release, for all 30 customers 2. What you'd build first, and why 3. One thing you'd keep manual, and why We're not looking for a perfect answer. Please don't read from a script or send an AI-written answer. If we detect one, the application is rejected. We want to hire a human, not a bot.