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.

As a Forward Deployed Engineer at Ascertain, you sit at the intersection of product, engineering, and our customers’ real-world operations. Healthcare organizations run on a patchwork of payer portals, practice management systems, spreadsheets, and legacy workflows. Your role is to deeply understand that reality and help shape Ascertain’s product so it works in practice, not just in theory.

You’ll work closely with customers to understand their workflows, constraints, and edge cases, and you’ll translate those insights into production-grade solutions using Ascertain’s platform. In practice, that might mean integrating with a legacy system, extending a workflow, building a new feature, or reconfiguring how our product is deployed often within the same week. Just as importantly, you’ll feed patterns back into the core product so we solve problems once, not repeatedly.

This is a founding Forward Deployed Engineer role. You won’t just execute against a defined playbook, you’ll help build it. As we scale, there’s a clear opportunity to grow into pod leadership and, over time, people management, if that’s a direction you’re interested in.

You’ll have meaningful autonomy to propose solutions and drive them forward, with clear escalation paths when tradeoffs or prioritization decisions are required.

This role is remote-friendly
, and we’re open to candidates based outside of NYC. For those who are NYC-based, we value in-person collaboration and expect regular time in our NYC office (typically ~2 days per week when you’re not traveling). Regardless of location, this role requires close product collaboration and occasional customer travel (roughly 10–20%).

• Partner directly with healthcare operators (practice managers, billing staff, and IT stakeholders) to understand real-world workflows, constraints, and edge cases and translate those insights into technical solutions.

• Shape how Ascertain’s product is deployed by configuring workflows, extending functionality, and integrating with external systems, ensuring solutions work in practice and not just in theory.

• Write production code across the stack, including new integrations, workflow extensions, features, internal tooling, and bug fixes, with an emphasis on reliability, scalability, and reuse.

• Identify patterns across customer engagements and drive product improvements so problems are solved once and scaled across customers, rather than repeatedly addressed in bespoke ways

• Collaborate closely with Product and Engineering to influence roadmap decisions based on firsthand customer insight and operational reality.

• You’ll occasionally partner with Sales on complex or novel opportunities, with an emphasis on technical feasibility and long-term product fit rather than ongoing deal support.

• Help define and document best practices for forward-deployed work at Ascertain, contributing to playbooks, standards, and patterns that will support future hires as the team grows.

• Over time, take on increasing ownership and leadership including mentoring newer team members, leading pods or initiatives, and helping shape how this function evolves as Ascertain scales.

• Several (2-5) years of experience as a software engineer, with a track record of shipping production systems and taking ownership from ambiguous problem definition through delivery.

• Strong programming skills (Python preferred), with experience building, extending, or maintaining integrations with external APIs, third-party systems, or imperfect data sources.

• Comfort…