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 Forward Deployed Engineer at Ascertain, you sit at the intersection of product, engineering, and real-world customer operations. Healthcare organizations run on complex, messy systems – payer portals, practice management systems, spreadsheets, and legacy workflows. Your job is to 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 translate their workflows and edge cases into production-grade solutions by integrating systems, extending workflows, and building features. Just as importantly, you’ll identify patterns and feed them back into the core product so we solve problems once and scale.

This is a founding Forward Deployed Engineer role. You’ll help define the playbook with clear opportunities to grow into pod leadership and, over time, people management, if that’s of interest.

This role is New York hybrid. 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%).

The role reports to the Chief Product Officer.

What You'll Need:

• Strong communication skills and experience in a customer-facing role.
• Several years of experience as a software engineer, with a track record of shipping production systems and owning work from ambiguous problem definition through delivery.
• 4+ years of experience in full stack development using Python, FastAPI, and TypeScript.
• Strong programming skills with experience building or integrating with external APIs, third-party systems, or imperfect data sources.
• Comfort working at the intersection of product, engineering, and customers — 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 you follow problems through to resolution.
• Comfort working in ambiguous, evolving environments, with the ability to create structure where none exists and adapt as priorities shift.
• 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, and you value getting to the right answer over being “right.”
• A customer-oriented lens grounded in curiosity and empathy — you seek to understand how and why people work the way they do, especially in complex or constrained environments.
• Interest in helping build something bigger than your individual contributions, whether that’s shaping playbooks, mentoring others, or taking on leadership responsibility as the team grows.

Benefits & Perks

• Meaningful work: Your work will directly impact healthcare organizations by reducing administrative burden and improving how care teams operate day to day.
• Ownership and growth: You’ll join Ascertain at an early stage, with meaningful equity and the opportunity to shape our product, technical direction, and how this function evolves over time.
• Competitive compensation: We offer a competitive salary, meaningful equity, comprehensive health benefits, and other standard benefits appropriate for a growing company.
• Flexible work model: This role is remote-friendly. For NYC-based team members, we support a hybrid model with regular in-office collaboration. We trust people to manage their time and work like adults.
• Collaborative team: You’ll work alongside a thoughtful, mission-driven team with backgrounds spanning healthcare operations, product, and engineering.

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