Staff Software Engineer

About the role

You will architect and own the core insurance infrastructure that powers Headway's platform across all 50 states. You will design and implement systems that determine patient eligibility, estimate insurance costs, and match patients to in-network providers in real time. You will build data-intensive pipelines that process millions of appointments and payer interactions every month with high reliability and accuracy. You will lead the implementation of ML models and automation that directly improve patient access and provider onboarding outcomes. You will mentor engineers within the insurance group and elevate the technical bar for design, code quality, and operational resilience. You will collaborate closely with product, operations, and data teams to turn complex payer rules and healthcare workflows into scalable software solutions. You will be responsible for delivering high-impact features that make Headway the trusted platform where care is not only paid for, but actually happens.

Key facts

What you'll do

• Design and implement the platform that determines patient eligibility and estimates insurance costs with high accuracy across all payer types and state rules.
• Build and maintain data pipelines that integrate with over 1,000 payers, normalizing messy provider and patient data into reliable signals for matching and pricing.
• Lead the development of the provider matching service that connects patients to in-network therapists based on coverage, specialty, and availability.
• Create and operate the claims processing system, including automated submission, denial analysis, and recovery workflows that improve cash flow for providers.
• Develop OCR and document intelligence capabilities that read insurance cards and policy documents to automate eligibility checks and reduce manual entry.
• Build and guide the implementation of machine learning models that improve price estimate accuracy and predict claim outcomes before submission.
• Create automation that replaces manual, spreadsheet-based credentialing and onboarding workflows for therapy practices, reducing time to first appointment.
• Implement human-in-the-loop automation that enables rapid scaling of provider onboarding while maintaining compliance and data correctness.
• Partner with operations and customer support teams to diagnose edge cases and improve the patient and provider experience across the insurance workflow.
• Write high-quality, testable code and maintain well-documented systems that allow other engineers to move quickly and safely.
• Mentor engineers, conduct code reviews, and drive architectural decisions that balance scalability, reliability, and time-to-market.
• Define and track key operational metrics for the insurance platform, using observability tools to drive improvements and prevent outages.

Requirements

• You are authorized to work in the country where the role is based and do not require sponsorship for this role at this time.
• You have 8+ years of professional software engineering experience building and operating production systems.
• You have 3+ years of experience building backend services with Python and TypeScript in production environments.
• You have deep experience with object-relational mappers like SQLAlchemy and complex query optimization across large datasets.
• You have hands-on experience with relational databases such as Postgres and data warehouses such as Snowflake.
• You have built and operated services in a cloud environment, with significant experience using AWS and container orchestration.
• You have experience with workflow orchestration and distributed systems tools such as Temporal and message platforms like Kafka.
• You have strong skills in monitoring and debugging live systems using tools like Datadog, Sentry, and PagerDuty.
• You have a track record of breaking down ambiguous problems, designing solutions, and shipping software that handles scale.

Nice to have

• Experience building and operating machine learning platforms and models in production.
• Experience with healthcare data standards, payer integrations, or prior work in insurance or benefits platforms.
• Experience with OCR and document parsing for healthcare or financial documents.
• Experience building developer tools, internal platforms, or self-service automation for engineering teams.

Practical notes

This role is full-time and remote. It requires authorization to work in the country where the position is based without the need for sponsorship. Only candidates who meet the listed requirements will be contacted for the next steps.