The Insurance Billing Engine: We apply AI pragmatically (blog) to reduce administrative burdens for providers and handle the burden of traditional billing workflows. You’ll scale the systems that handle the unique, often nonsensical rules of every major insurance payer to accurately estimate and file claims hundreds of thousands of times per month.
Patient-First Infrastructure: We’re moving toward a patient-centric model. Build the backend services that power personalized care recommendations, health tracking, and longitudinal data views as well as innovative user experiences to help patients find a therapist that meets their needs
Financial Integrity: Work on the ledger systems that ensure 70,000+ providers get paid accurately. This requires building for idempotency and strict consistency in a multi-party marketplace.
Our Stack
Languages: Python, TypeScript
Storage: Postgres, Redis, Snowflake
Infrastructure: AWS, Temporal
Ops: Datadog, Sentry, PagerDuty
AI Tools: Cursor, Claude, Gemini, Eddy (our in-house cloud agent harness)
Who You Are
Owns 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.
Sets the Technical Standard: You make technical decisions that optimize for maintainability and scale, not just shipping speed. You proactively improve your team’s engineering velocity – whether that’s refining tooling, improving automation, or establishing patterns that prevent entire categories of bugs.
Mentor by Default: You pull engineers into design discussions without being asked. Your code reviews teach, not just gatekeep. You make sure knowledge gets shared across the team, not siloed in one person’s head.
Ships Fast, Iterates Faster: You can move from problem statement to working solution quickly. You’d rather ship a good v1 this week than a perfect v1 next month. Real feedback from therapists and patients is worth more than another round of design review.
Quick Study in Complex Domains: Healthcare is a maze of payers, regulations, and exceptions. You don’t need prior healthcare experience, but you need to be someone who dives into unfamiliar domains and builds a working mental model fast.
Motivated by Impact: You want your engineering skills applied to problems that matter. Mental healthcare access is broken in America, and you want to be part of fixing it.
Communicates with Precision: Whether it’s a Slack thread, a design doc, or a cross-team meeting, you communicate clearly and concisely. You know that great engineering is wasted if you can’t bring people along.
AI Frontier Tinkerer: You don’t just use AI tools – you push their limits. You’ve experimented with applying LLMs to real workflows, whether that’s code generation, operational automation, or developer tooling. You bring a builder’s mindset: what can we automate, what should stay human, and how do we ship it responsibly in healthcare?
Our interview process
After you apply to Headway, here are some details of what to expect during the interview process.
Initial screen: You’ll connect with someone in recruiting so you can learn more about the team, Headway’s mission and exciting growth, and we can get a better idea of your background.
First round: You’ll meet with an engineer on the team to do some live coding and learn more about the engineering team.
Final rounds: You’ll meet several more 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 of the details, including specifics on employee equity, and congratulatory messages from excited future team members!
Compensation & Benefits
Salary: $182,750 – $278,500 base salary plus a competitive equity package.
Comprehensive Benefits: Medical, dental, vision, HSA/FSA, 401(k), Carrot Fertility reimbursement, and 16-week parental leave.
The Mission: We reimburse your therapy and provide a professional development budget. We believe in what we’re building.
Time Off: 13 holidays, a full week off in December, and flexible PTO.
#LI-BM1
We believe a team’s strength is in its people, and we cannot achieve this mission without a team that reflects the diversity of this problem – across race, ethnicity, gender, sexuality, age, national origin, religion, family status, disability, military status, and experience. Headway is committed to the full inclusion of all qualified individuals. As part of this commitment, Headway will ensure that persons with disabilities are provided with reasonable accommodations. If reasonable accommodation is needed to participate in the job application or interview process, to perform essential job functions, and/or receive other benefits and privileges of employment, please inform the recruiter when they contact you to schedule your interview.
Headway participates in E-Verify. To learn more, click here.
A notice to Headway applicants: To protect yourself against phishing and recruitment fraud, please note that Headway only accepts applications through our official careers page at https://headway.co/careers. Headway will never refer you to external websites, ask for payment or personal information, or conduct interviews via messaging apps. All official communication will come from a @findheadway.com email address. If you are contacted by someone claiming to be from Headway via an unofficial channel, please do not share any information and report it as spam.
