Meet Ascertain Ascertain is building AI agents to automate the administrative work that burdens care teams. We are in major health systems and large specialty groups, saving hundreds of staff hours every week. Our backers include Northwell Health, New York’s largest health system, and Deerfield Management, a leading healthcare investment firm. Together, we’re on a mission to restore time, trust, and focus to the people who keep healthcare running. Our work is urgent — not because of startup timelines, but because our customers rely on us to drive financial resilience and operational clarity in a system under strain. About the job We're hiring a Staff Product Manager, Automation to own the core automation platform that makes this possible. This role sits at the intersection of LLM-powered agents, workflow automation, and healthcare operations. You'll work hand-in-hand with engineering, operations, and deployment teams to decide what our agents can reliably automate next, how we measure their performance in the real world, and how we scale across the many complexities of healthcare. What you'll do Own the roadmap for our automation vertical. from problem definition and opportunity sizing through agent design, rollout, and measurable outcomes in production. Partner with operations and engineering to translate messy real-world workflows into agent-executable specs. Shadow ops teams, reverse-engineer payer portals, read denial letters, and turn all of it into structured requirements an agent can act on. Define the evaluation and observability story for your agents. Manage the metrics, evals, guardrails, and human-in-the-loop escalation paths. Prioritize ruthlessly across competing customer asks, platform investments, and net-new automation surfaces. Decide what becomes productized vs. what stays bespoke. Partner with GTM on positioning, pricing signals, and customer expansion - automation ROI is the story, and you'll help tell it with the data to back it up. What you'll need 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. Benefits & Perks Meaningful work: Your work will directly impact healthcare organizations by reducing administrative burden and improving how care teams operate day to day. Ownership and growth: You’ll join Ascertain at an early stage, with meaningful equity and the opportunity to shape our product, technical direction, and how this function evolves over time. Competitive compensation: We offer a competitive salary, meaningful equity, comprehensive health benefits, and other standard benefits appropriate for a growing company. Flexible work model: This role is remote-friendly. For NYC-based team members, we support a hybrid model with regular in-office collaboration. We trust people to manage their time and work like adults. Collaborative team: You’ll work alongside a thoughtful, mission-driven team with backgrounds spanning healthcare operations, product, and engineering. Why Ascertain? Make a real difference: Your work will directly impact healthcare organizations and improve patient care. Join Ascertain in transforming healthcare with AI!