Forward Deployed Engineer

Ascertain

10d • Hybrid

About The Position

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%).

Requirements

• 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 operating at the intersection of product, engineering and customers, including working directly with non-technical stakeholders and translating real-world needs into scalable technical solutions.
• Proven ability to manage complexity and context-switch effectively across multiple workstreams without dropping details or momentum.
• Sound technical judgment: you can assess tradeoffs, identify when something should become a productized solution, and know when to invest in robustness versus speed.
• Curiosity and empathy for how customers actually work, especially in messy or regulated environments; you seek to understand why before “prescribing” solutions.
• Clear communication skills, both written and verbal, enabling you to collaborate effectively across Product, Engineering, Sales, and Customer teams.

Nice To Haves

• 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.

Responsibilities

• 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.

Benefits

• 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.

What This Job Offers

• Job Type: Full-time
• Career Level: Mid Level
• Education Level: No Education Listed