Technical Customer 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.

Healthcare organizations don't run on clean data and modern APIs. They run on payer portals, practice management systems, spreadsheets, manual workarounds, and institutional knowledge that lives in people's heads. Your job is to work inside that reality and make Ascertain's product deliver results there.

This role sits at the boundary between our product and our customers' operations. You'll spend time with billing teams, revenue cycle leaders, and IT departments understanding how their workflows actually function, then build the integrations, extensions, and features that make our system work in their environment. When you spot patterns across customers, you'll feed them back into the core product so we solve problems once and scale. There will be ~10-20% travel to customer sites.

This is a hands-on role. You will write code, build integrations, and ship features end-to-end. You will also be the person our customers trust to understand their problems and follow through on solving them. Your work will directly improve how healthcare organizations operate and, downstream, how patients experience care. This is a founding role on a small team where your judgment and contributions shape the product and the company.

Monday you're on-site with a health system's billing team, mapping how they handle claim denials and identifying where our agent can plug in. Tuesday you're writing an integration against their practice management system. Wednesday you're pairing with the Ascertain product team to generalize what you learned into a reusable workflow. Thursday a different customer hits an edge case in production and you're triaging it, talking them through the issue, and shipping a fix. Friday you're documenting what you built so the next engineer doesn't start from scratch.

• This role requires frequent, unscripted conversations with hospital administrators, billing teams, and clinical operations staff. You need to communicate clearly, build rapport quickly, and hold your own in rooms where you're the only technical person.

• Proven experience working directly with customers or external stakeholders in a technical capacity, not just presenting to them, but diagnosing problems, gathering requirements, and explaining technical tradeoffs in plain language.

• The ability to build trust with people who aren't engineers: billing managers, revenue cycle directors, clinical operations leads. You're someone they feel comfortable calling when something isn't working.

• Comfort navigating ambiguity. Customers don't hand you clean specs. You figure out what they need, often before they can articulate it themselves.

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

• Full-stack experience with Python (required), FastAPI and TypeScript (preferred).

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

• You write solid, reliable code. You don't need to be the strongest engineer in the room, but your work needs to hold up in production and you need to understand systems well enough to make good decisions independently.

• You take ownership of outcomes, not tasks. When something breaks for a customer, you don't wait for a ticket to be assigned.

• You have good judgment about when to move fast and when to invest in something durable. Not everything needs to be generalized, and not everything should be a one-off.

• You're interested in helping build the playbook for how Ascertain works with customers, not just executing against an existing one.

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