Senior Product Engineer

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.

As a Senior Product Engineer, you’ll operate at the intersection of engineering, product, and real-world customer workflows. You won’t just build software—you’ll take ownership of messy, high-stakes problems and turn them into systems that actually work in production. This is a hands-on engineering role: you will write code, build integrations, and ship features end-to-end.

This role requires you to be equally comfortable in two modes:

• Deep in the code: designing systems, writing production Python, debugging issues, and improving reliability

• In front of customers: asking the right questions, understanding constraints, and clearly explaining how the system works.

You will translate messy operational problems into technical solutions—and then translate those solutions back into clear, practical terms for non-technical stakeholders.

This role is hybrid based in NYC with occasional customer travel (~10–20%).

• Strong communication skills and proven experience working directly with customers or external stakeholders in a technical capacity (required)

• 4+ years of experience as a software engineer, with a track record of shipping production systems end-to-end

• Strong full-stack experience with FastAPI and TypeScript

• Experience building or integrating with external APIs, third-party systems, or imperfect data sources

• Startup experience preferred

• 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

Why Ascertain? Make a real difference: Your work will directly impact healthcare organizations and improve patient care. Join Ascertain in transforming healthcare with AI!