Applied AI/ML Software 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 Job

As a Product Engineer in AI at Ascertain, you will own the development and optimization of agents that automate healthcare back-office workflows. This is a hands-on role: you'll configure and iterate on agentic systems, write production code when needed, and work directly with customers and our operations team to deeply understand user workflows and continuously improve performance.

You'll be responsible for building reliable agents to solve real problems, establishing QA processes and evals, analyzing call data, and using what you learn to optimize every aspect of how we deliver agentic software.

This role is based in our NYC office with a hybrid schedule.

What You’ll Do

• Design, build, and optimize production-grade voice agents using third-party platforms and internal tooling

• Own end-to-end quality of agent performance, including QA processes, evaluation frameworks, and continuous monitoring

• Analyze call transcripts and interaction data to identify failure modes and drive systematic improvements

• Work directly with customers and internal operations teams to understand workflows and translate them into scalable product solutions

• Collaborate with engineering to build and improve reliability, observability, and deployment infrastructure

• Write and maintain production Python code for integrations, APIs, and custom agent logic

• Contribute to product direction by bringing a strong user and workflow perspective into development decisions

What You’ll Need

• 4+ years of professional software engineering experience, including owning production systems end-to-end (shipping, debugging, monitoring, and continuously improving reliability)

• At least 2+ years of hands-on Python experience in a professional setting (not academic or personal projects), including building APIs, services, or data workflows

• Experience working cross-functionally with non-technical stakeholders

• Proven ability to operate in ambiguous environments and drive projects from undefined problem → shipped solution

• Experience building or working with conversational systems, voice AI, or LLM-based applications, with familiarity in telephony (e.g., Twilio) or real-time communication platforms is preferred

What You'll Bring to the Table

• You're a builder who cares as much about the user experience as the technical implementation

• You take ownership of outcomes, not just tasks

• You communicate clearly and build trust with operations, engineering, and customers alike

• You're excited to work at the intersection of product and engineering, and you see this blended role as a feature, not a compromise

• You thrive in early-stage environments where scope evolves and you're expected to figure things out

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