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 Role Ascertain is hiring a Software Engineer (Brazil-based) to support the deployment and integration of our AI-powered healthcare platform.

This role is focused on operationalizing software in real-world production environments. You’ll work closely with senior engineers and deployment leads to implement integrations, configure workflows, and ensure our systems run reliably and accurately in live settings.

This is an excellent opportunity for an engineer who enjoys hands-on technical execution, values precision and structure, and wants exposure to how AI-powered software is delivered at scale—with room to grow into broader engineering responsibilities over time.

What You’ll Do

• Implement and maintain integration pipelines with external partners
• Configure and deploy product updates in collaboration with engineering and operations
• Work with REST APIs, JSON payloads, and Python scripts to support integrations
• Validate data flows, execute test cases, and troubleshoot deployment issues
• Monitor production workflows and help ensure system reliability
• Write clean, well-documented code following internal engineering standards
• Collaborate asynchronously via Slack and Linear within sprint cycles

What You’ll Need

• 4+ years of experience in a technical role (engineering, IT, or data-focused work)
• Experience working with REST APIs and JSON
• Solid scripting and troubleshooting skills (Python preferred)
• Strong attention to detail and ability to follow technical specifications precisely
• Clear written communication skills and comfort working in an async environment

What Will Help You Thrive

• A methodical, execution-oriented mindset
• Comfort working within defined processes and deployment playbooks
• Pride in accuracy, consistency, and reliability
• Comfort asking questions, flagging blockers, and collaborating asynchronously.
• Curiosity about how AI-powered systems are implemented in healthcare

A proactive attitude and genuine curiosity about how software is delivered and used in the real world.

Why Ascertain? Make a real difference: Your work will directly impact healthcare organizations and improve patient care. Join Ascertain in transforming healthcare with AI! Compensation Range: $50K - $70K