1 in 4 people in the US have a treatable mental health condition, but most providers don't accept insurance, making therapy too expensive for most people. Headway’s mission is to fix this by building a new mental healthcare system everyone can access. We started by solving the biggest barrier to care: insurance. The admin work - credentialing, claims, payment reconciliation - is a nightmare. We've automated that.

But we're going further. Over 75,000 providers across all 50 states run their practice on our software, serving over 1 million patients. We are building the best tools for therapists to run their entire practice, reimagining the experience of finding a therapist, and investing in the platform foundations to enable this at scale. We aren't just a billing layer; we are becoming the platform where care actually happens.

We're a Series D company with $325M+ in funding (a16z, Accel, Spark Capital, etc.), looking for exceptional people to help us achieve this mission. We want your time here to be the most meaningful experience of your career. Join us, and help change mental healthcare for the better.

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.]

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.

1 in 4 people in the US have a treatable mental health condition, but most providers don't accept insurance, making therapy too expensive for most people. Headway’s mission is to fix this by building a new mental healthcare system everyone can access. We started by solving the biggest barrier to care: insurance. The admin work - credentialing, claims, payment reconciliation - is a nightmare. We've automated that.

But we're going further. Over 75,000 providers across all 50 states run their practice on our software, serving over 1 million patients. We are building the best tools for therapists to run their entire practice, reimagining the experience of finding a therapist, and investing in the platform foundations to enable this at scale. We aren't just a billing layer; we are becoming the platform where care actually happens.

We're a Series D company with $325M+ in funding (a16z, Accel, Spark Capital, etc.), looking for exceptional people to help us achieve this mission. We want your time here to be the most meaningful experience of your career. Join us, and help change mental healthcare for the better.

About The Role

As Staff Data Scientist for Commercial GTM, you will be the overall owner of data science for Headway's commercial business. You will report into the Payer data team and will build a data science roadmap directly with Headway's Chief Commercial Officer. Accurate, proactive commercial insight is a core driver of Headway's growth, and this role is the analytical engine behind it. You will spend the majority of your time on proactive strategic analyses for the Chief Commercial Officer and for Headway's most important accounts. You will partner closely with Commercial, Payer, Finance, Product, and Operations leadership to define the right questions, uncover opportunities, and turn insights into measurable outcomes — while serving as the technical anchor for other data scientists working across our commercial agreements.

What you will do

Everything in the Senior role, plus:

• Own the commercial data science roadmap end to end, building it directly with Headway's Chief Commercial Officer and aligning it to the priorities of the Payer pillar.

• Lead proactive strategic analyses for the Chief Commercial Officer and for Headway's most important accounts — where you'll spend the majority of your time.

• Serve as a watchtower for the key metrics across all commercial agreements, surfacing risks and opportunities before they become problems.

• Enable self-service analytics for the commercial team, building the definitions, dashboards, and durable assets that let partners answer their own questions with confidence.

• Serve as technical lead for other data scientists working on commercial, providing strong technical review, mentorship, and raising the bar for rigor.

• Translate complex technical findings into clear, actionable recommendations for executive stakeholders.

What will make you successful

• 10+ years of experience in data science or analytics roles.

• Strong executive presence and stakeholder management skills, with a proven ability to earn trust and build a roadmap directly with senior and executive partners.

• Significant go-to-market experience and specialization is strongly preferred; strong candidates who meet our other criteria and are eager to build go-to-market expertise are also encouraged to apply.

• Proven success partnering cross-functionally with Commercial, Payer, Finance, Product, and Operations teams.

• Expertise in forecasting and causal inference, including common failure modes and how to design around them.

• Expert fluency in SQL and strong proficiency in Python or R, including building reliable, reusable analytical workflows; experience with data modeling, ideally using dbt.

• Experience adopting and championing AI-assisted tools to accelerate and automate data workflows.

• A track record of influencing executive decisions with clear recommendations and measurable outcomes.

Why this role is exciting

• Own commercial data science end to end and shape the strategy of Headway's businesses.

• Partner directly with the Chief Commercial Officer and executive leadership to influence company strategy and growth.

• Serve as the technical anchor for a growing data science team working on Headway's most important accounts.

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.

1 in 4 people in the US have a treatable mental health condition, but most providers don't accept insurance, making therapy too expensive for most people. Headway’s mission is to fix this by building a new mental healthcare system everyone can access. We started by solving the biggest barrier to care: insurance. The admin work - credentialing, claims, payment reconciliation - is a nightmare. We've automated that.

But we're going further. Over 75,000 providers across all 50 states run their practice on our software, serving over 1 million patients. We are building the best tools for therapists to run their entire practice, reimagining the experience of finding a therapist, and investing in the platform foundations to enable this at scale. We aren't just a billing layer; we are becoming the platform where care actually happens.

We're a Series D company with $325M+ in funding (a16z, Accel, Spark Capital, etc.), looking for exceptional people to help us achieve this mission. We want your time here to be the most meaningful experience of your career. Join us, and help change mental healthcare for the better.

The Work

Fullstack at Headway means end-to-end ownership. You're building reliable abstraction layers over a fragmented healthcare system and translating them into seamless, empathetic user experiences. What you could work on:

• Therapist Practice Management: Build a best-in-class platform for Headway therapists to run their businesses. You'll own features from the database schema to the UI, creating intuitive web experiences for scheduling, AI-assisted clinical documentation, and payment management.

• Patient & Provider Engagement: Deepen the relationship between patients and their care. Build the interfaces and APIs that power seamless communication, personalized experiences, and tools that keep patients connected to their providers — and providers focused on what matters most.

• The Modern AI-Enabled Clinical System: Help design and build the systems that manage clinical data. Create high-integrity experiences for treatment plans and progress notes, integrating AI-powered clinical intelligence to give providers their time back.

• Frictionless Onboarding: Turn the historically painful process of insurance credentialing into a sleek, consumer-grade experience. Build products and tooling to get providers in-network and scaling their practice in record time.

• Growing the Network: Own the tools and experiences that expand Headway's reach — from acquiring new providers to empowering existing ones to bring their patients onto the platform. Build the infrastructure that fuels sustainable, high-quality growth.

• Technical foundations: Help the teams see around corners and lay the technical foundations for the future of our product. Build systems, tools, and processes that enable the team to ship innovative products quickly, safely, and reliably.

• Strategic leadership: As a Staff Engineer, you will work with a cross functional leadership team to shape the roadmap and technical strategy for the space.

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

• End-to-End Product Builder: You care just as much about the API architecture as you do the user experience. You seamlessly context-switch between backend logic and frontend state management.

• 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 do a live coding interview with Karat, our technical interviewing partner. It's a great opportunity to showcase your problem-solving skills and learn more about what our engineering team is building.

• 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 of the details, including specifics on employee equity, and congratulatory messages from excited future team members!

Compensation & Benefits

• Salary: $264,000 - $330,000 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.