Staff Software Engineer - Insurance

Staff Software Engineer (Insurance)

The Work

The Insurance team is the backbone of Headway's business. We deliver the two core promises of the platform: affordable therapy covered by insurance for patients, and a simple way to run a therapy practice for providers. Every appointment on Headway flows through systems our team owns — from identifying whether a patient is eligible, to estimating their cost, to matching them with a provider, to submitting a clean claim.

This is a deep and wide problem. We operate across all 50 states, 1,000+ payers, and millions of appointments every month. There's a lot of data to make sense of and signal to find in the noise. As Headway's network grows — more patients, more providers, more payers — the accuracy, reliability, and automation of these systems become the difference between a business that scales and one that doesn't.

As a staff engineer in the group, you will lead design and implementation of the systems that power Headway's insurance operations — patient identification, pricing estimates, provider matching, and claims. Build data-intensive, ML-powered platforms that serve patients and providers and learn from every visit, mentor engineers, and write high-impact code at the intersection of healthcare data and payer operations.

Some examples of what that work looks like in practice:

• Building a new ML model that lifted price estimate accuracy by 10+ percentage points, getting tens of thousands of patients a better estimate ahead of their first session

• An OCR pipeline to read patient insurance cards, automate eligibility checks, and run ML models to detect complex insurance arrangements — improving onboarding and first-claim success rates

• A claims AI agent that reviews denied claims, identifies root causes, and resubmits autonomously — recovering hundreds of thousands of dollars and proving we can build self-healing systems at scale

• A human-in-the-loop automation that transformed a 20-step manual credentialing process in Google Sheets into an average of 2 days and 1 task — with a record of 6 seconds start to finish — enabling providers to onboard faster and expand their reach to new patients

Our Stack

• Languages: TypeScript, Python 3

• Frontend: React, Remix, Next.js

• Backend & Storage: FastAPI, SQLAlchemy, Postgres, Redis, Snowflake

• Infrastructure: AWS, Temporal, Kafka

• Ops: Datadog, Sentry, PagerDuty

• AI Tools: Cursor, Claude, Gemini, Eddy (our in-house cloud agent harness)

Who You Are

• A platform thinker. You build for the teams behind you, not just the immediate use case. You create abstractions that let others move faster and more safely.

• Drawn to signal in messy data. Payer rules vary by state, plan, and policy. You find the structure in the noise and build systems that reason about it reliably.

• Hands-on. You write code where leverage is highest and hold yourself to the same bar you hold others.

• Own outcomes, not tasks. You've been handed ambiguous problems and turned them into shipped software. You know how to define the solution, pull in the right people across teams, and keep things moving when priorities shift.

• Communicate with precision. Whether it's a design doc, a Slack thread, or a cross-team meeting — you bring people along.

Our Interview Process

• Initial screen: You'll connect with someone in recruiting to learn more about the team, Headway's mission, and our growth — and we'll get a better sense of your background.

• Tech & Team Fit round: AI Coding and Hiring Manager Chat.

• Final rounds: You'll meet several team members for technical and non-technical interviews and leave with a fuller picture of what it's like to work at Headway.

• References and the offer: Our favorite part of the process. We'll send over all the details, including specifics on employee equity, and congratulatory messages from excited future teammates. 

Compensation and Benefits:

The expected base pay range for this position is $224,000-$336,000 based on a variety of factors including qualifications, experience, and geographic location. In addition to base salary, this role may be eligible for an equity grant, depending on the position and level.

We are committed to offering a comprehensive and competitive total rewards package, including robust health and wellness benefits, retirement savings, and meaningful ownership opportunities through equity. Compensation decisions are made holistically, ensuring fairness and alignment with market benchmarks while recognizing individual contributions and potential.

• Benefits offered include:

  • Equity compensation

  • Medical, Dental, and Vision coverage

  • HSA / FSA

  • 401K

  • Work-from-Home Stipend

  • Therapy Reimbursement

  • 16-week parental leave for eligible employees

  • Carrot Fertility annual reimbursement and membership

  • 13 paid holidays each year as well as a Holiday Break during the week between December 25th and December 31st

  • Flexible PTO

  • Employee Assistance Program (EAP)

  • Training and professional development

[To be included if role is bonus eligible][Other compensation includes: discretionary bonuses and/or commission. Commission payments are monthly.]