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Role Description

As a Forward Deployed Engineer at Ascertain, you sit at the intersection of product, engineering, and real-world customer operations. Your job is to understand the complex, messy systems healthcare organizations run on and help shape Ascertain’s product so it works in practice, not just in theory.

• Work closely with customers to translate their workflows and edge cases into production-grade solutions.
• Integrate systems, extend workflows, and build features.
• Identify patterns and feed them back into the core product to solve problems once and scale.
• Define the playbook with clear opportunities to grow into pod leadership and, over time, people management.

This role is US-based remote, requiring close product collaboration and occasional customer travel (roughly 10–20%). The role reports to the Chief Product Officer.

Qualifications

• 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.
• Proven ability to manage complexity and context-switch across multiple workstreams without losing momentum or detail.
• Startup experience preferred.

Requirements

• 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.
• A customer-oriented lens grounded in curiosity and empathy.
• Interest in helping build something bigger than your individual contributions.

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.
• Collaborative team: You’ll work alongside a thoughtful, mission-driven team with backgrounds spanning healthcare operations, product, and engineering.