Customer-Facing Product 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 Customer-Facing Product Engineer at Ascertain, you are a full-stack engineer responsible for building and shipping production systems that power real-world healthcare workflows. Healthcare organizations run on complex, messy systems—payer portals, practice management systems, spreadsheets, and legacy tools. Your job is to design and build software that works in these environments, integrating systems, extending workflows, and turning ambiguity into reliable, scalable solutions. You will work directly with customers to understand how their operations actually function, then translate those workflows into production-grade systems. This is a hands-on engineering role: you will be writing code, building integrations, and shipping features end-to-end. Just as importantly, you will identify patterns across customers and feed them back into the core product so we solve problems once and scale. This role is remote in the USA with occasional customer travel (~10–20%). What You'll Need Strong English language and communication skills and proven experience working directly with customers or external stakeholders in a technical capacity 4+ years of experience as a software engineer, with a track record of shipping production systems end-to-end Strong full-stack experience (Python experience is a must, FastAPI, and TypeScript preferred) Strong programming skills with experience building or integrating with external APIs, third-party systems, or imperfect data sources Experience working at the intersection of product and engineering, including translating real-world needs into scalable technical solutions Proven ability to manage complexity and context-switch across multiple workstreams without losing momentum or detail Startup experience preferred What You'll Bring to the Table A strong sense of ownership: you take responsibility for outcomes, not just tasks, and follow problems through to resolution Comfort working in ambiguous, evolving environments, with the ability to create structure where none exists Thoughtful technical judgment, including knowing when to move quickly and when to invest in durability, reuse, or productization A collaborative mindset and low ego: you’re comfortable partnering across Product, Engineering, Sales, and Customer teams A customer-oriented mindset grounded in real experience working directly with users Interest in helping build something bigger than your individual contributions, including shaping playbooks and taking on leadership over time Why Ascertain? Make a real difference: Your work will directly impact healthcare organizations and improve patient care. Join Ascertain in transforming healthcare with AI!