Forward Deployed Engineer

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 ROLE As a Forward Deployed Engineer, you will own the full arc of a customer deployment: understanding a practice's workflows in depth, building the integrations that connect Ascertain's agents to their systems, and shipping the result into production. You will work directly with billers, referral coordinators, practice administrators, and clinical staff to map their processes, then translate what you learn into working software. The role combines substantive engineering work with sustained customer engagement. FDEs are the technical owners of their deployments—you’ll collaborate with the customer, write production code, and be the person in the room when customers raise difficult questions. WHAT YOU'LL DO • Embed with new and existing customer practices, remotely and on-site, to map prior authorization, referral, and related workflows end to end. • Build and own the integrations that connect Ascertain's agents to customer systems: EHR APIs (Athena, eClinicalWorks, Epic, etc.), payer portals, fax and EDI, document intake, and the rest of the practice's stack. • Configure and extend our agent platform for each customer—ontology, prompts, tools, guardrails, escalation paths—and harden what works into reusable patterns. • Debug production issues across the full stack: data, prompts, APIs, UI, and the surrounding human workflow. • Serve as the technical voice in customer conversations. Translate between clinical-operations language and engineering, and make informed decisions on what to build, what to configure, and what to decline. • Surface learnings to the product and platform teams so patterns discovered once become reusable. WHAT WE'RE LOOKING FOR Required • 5+ years shipping production code in a commercial engineering role. • Fluent in Python • Proficient with SQL, REST APIs, and at least one full-stack or front-end framework. • A track record of delivering in environments where the problem was not fully specified - early-stage startup, consulting, applied research, or an operations-heavy role. • Strong written and verbal communication. You can lead a working session with a non-technical practice manager and produce a concise specification afterward. • Willingness to travel occasionally to customer sites. Strongly preferred • Healthcare experience: EHRs, claims and EDI (X12 270/271, 278, 837), HL7/FHIR, payer portals, RCM, or prior authorization workflows specifically. • Production experience with LLMs or agent frameworks—prompt design, evaluations, tool use, retrieval, guardrails. • Applied integration experience: OAuth flows, webhook plumbing, browser automation, PDF and document parsing. • Prior experience as an embedded engineer working directly with enterprise customers. This role will not suit you if • You prefer a well-defined backlog of tickets. • You are looking to specialize deeply in a single technical area. • You do not want regular, direct customer interaction as part of your day-to-day work. Why Ascertain? Make a real difference: Your work will directly impact healthcare organizations and improve patient care. Join Ascertain in transforming healthcare with AI! Compensation: $130K - $175K