Senior Backend Software Engineer

The Work

Backend at Headway involves high-stakes logic. You’re building a reliable abstraction layer over a fragmented healthcare system. What you could work on:

• The Modern AI-enabled Clinical System: Help design and build the systems that store and manage clinical data. This isn't just a database; it's a high-integrity system for treatment plans, progress notes, patient history, and AI-powered clinical intelligence - from session transcript-to-note generation to automated summaries that give providers their time back.

• 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.

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