ascertain - Staff Product Manager, Automation

• 8+ years of product management experience, with meaningful time spent on technical, platform, or workflow-automation products (not just consumer features). • A demonstrated track record of shipping products that involve integrating with messy, legacy, or enterprise systems - EHRs, payer systems, ERPs, imaging systems, or similarly gnarly backends. • Fluency with modern AI/ML systems - LLMs, agents, RAG, evals, tool use. You don't need to train models, but you need to credibly scope what an agent can and can't do, and push back when engineering over- or under-promises. • Strong analytical chops - you're comfortable in SQL, notebooks, or whatever it takes to answer your own product questions without waiting on a data team. • Experience working in zero-to-one or early-scaling environments where the product, the customer, and the operating model are all being figured out in parallel. • Excellent written communication. You can turn a chaotic customer workflow into a crisp spec, a deployment postmortem into a roadmap item, and a technical tradeoff into a decision the exec team can make in ten minutes. • How you can stand out • Healthcare experience is a strong plus but we'll take a strong technical PM from an adjacent high-complexity domain who's hungry to go deep on healthcare. • Builders encouraged. Whether an ex-engineer or a hobbyist that’s created tools for themselves, the best way to understand product is to have experience shipping yourself • Ex-founders/early-stage employees. You’re willing to do whatever it takes to push the organization forward and have experience doing so. • A genuine belief that healthcare administration is worth fixing.