Staff Engineer - Experimentation Platform at Headway

Headway.co; United States; Remote; USD 265,000 - 331,000; Full time

Benefits offered by this job

Medical, dental, vision

HSA/FSA

401(k) with match

Fertility reimbursement

Paid parental leave

Job summary

Headway is seeking a Staff Software Engineer to own and evolve the experimentation platform that powers patient-therapist matching, provider onboarding, and AI-enabled workflows. You will design end‑to‑end experiment pipelines, exposure, and identity resolution across devices, while working with multiple teams to ensure reliable results.

You will mentor engineers, shape the feature-flagging stack, and partner with Data Science to bring rigorous statistics into day-to-day decision making.

Qualifications

• Experience owning an experimentation or feature-flagging stack end-to-end.
• Ability to partner with data scientists using statistics to validate experiments.
• Proven track record influencing multiple teams and roadmaps.

Responsibilities

• Own assignment, exposure, and the experiment data pipelines across teams.
• Evaluate and consolidate experimentation and feature-flagging architectures.
• Collaborate with data science and product teams to ensure valid results.
• Mentor senior engineers and raise the platform's reliability and reach.

Skills

Statistics

Platform ownership

Tools

LaunchDarkly

Statsig

dbt

Snowflake

Job description

Staff Engineer - Experimentation Platform at Headway in Wilmington

Compensation vs. Market: The $265K–$331K base range is top-of-market for Staff Engineers in the US, sitting well above the median Staff SWE salary of roughly $220K–$260K at comparable Series D companies. The equity component adds further upside at a company with $325M+ in funding and clear growth momentum.

Career Development: This role is a rare opportunity to own a horizontal platform that every team at the company depends on. Skills developed here — experimentation infrastructure, causal inference at scale, identity resolution, multi-sided marketplace testing — are among the most in-demand in growth engineering and data-platform roles at top-tier tech companies.

• Green flags: Clear technical mandate with real autonomy; cross-functional influence across 11 teams; data science partnership; explicit mention of AI integration in workflows; mission-driven context in a regulated, high-impact industry.


• Green flag — culture: \"Optimize for trust\" and psychological safety language signals a healthy learning culture, not a blame-first environment.


• Potential challenge: The role is 50% platform engineering and 50% program management / internal education. If you prefer pure IC coding work, the stakeholder and roadmap-sequencing demands may feel heavy.


• Growth stage: Series D with 90K+ providers signals product-market fit is proven — lower existential risk than early-stage, but still plenty of greenfield technical work ahead.

For engineers who want their legacy to be raising the floor for an entire organization's decision‑making quality, this is an unusually well‑scoped Staff role. The build‑vs‑buy decisions on LaunchDarkly/Statsig alone will be notable resume‑worthy work.

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.

Over 90,000 providers across all 50 states run their practice on our software, serving over 2.6 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 — and building much of it with AI. 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 Engineering at Headway

Building a new mental healthcare system at Headway is only possible because of the scale and leverage that software can provide. The engineering team is a small but mighty team using technology to build that future.

Principles that guide us:

• Focus on the mission: We view software as a means of effecting change in the world, not as an end unto itself. We write software to empower our patients and therapists to better solve the problems they're facing.


• Ship small, learn fast: We are building new and novel products and believe that we learn what our users need by quickly shipping and iterating.


• Everything is a product: Whether it's our patient search experience or a developer productivity improvement, we treat everything we build at Headway as a product with end‑users in mind.


• Optimize for trust: We believe that engineers should be continually learning. To learn effectively and to be productive, engineers must feel safe asking questions and discussing mistakes.

Tools We Use

• Languages: Python 3, TypeScript


• Libraries & Frameworks: FastAPI, SQLAlchemy, React, Remix


• Infrastructure: AWS (Fargate, ECS, S3, and more), Cloudflare, Spark, Kafka


• Version Control: GitHub

About the Role

We are looking for a Staff Software Engineer to own how Headway runs experiments. \"Ship small, learn fast\" is a core principle, and experimentation is how we actually do it: eleven teams have run hundreds of experiments deciding how patients find a therapist, how quickly new providers get up and running, whether our AI products are working, and how we collect the clinical outcomes data that proves care is effective. You will own the platform all of that runs on.

This is a hands‑on technical leadership role with unusually wide reach. You will:

• Design and build core primitives — including how users are assigned to experiments, how we record what someone actually saw, and how we recognize the same person across devices and between browsing anonymously and signing in.


• Decide what our long‑term experimentation and feature flagging stack should be. We run LaunchDarkly and Statsig today, and that architecture is yours to evaluate and consolidate.


• Make AI a real part of the workflow — from validating an experiment's setup before it starts to catching a broken experiment automatically instead of discovering it in a Slack thread a week later.

You will also evolve our experimentation capabilities to expand into market‑based testing. Headway is a multi‑sided marketplace, so we frequently need to change something for therapists and measure what happens to patients — which changes both how a test must be designed and how it can be analyzed. We need to test whole geographic markets, not just individual users, and hold groups out for long stretches to understand real long‑term impact.

The job is a platform and a program in equal measure. Half of it is the technical foundation. The other half is raising how well the whole company experiments: the defaults, the review, the documentation, and the education that let a team run a trustworthy experiment without needing you in the room. You will gather needs from teams who all want something different, sequence them into a roadmap, and say no clearly — acting as part technical product manager for your own platform.

You will sit in the Patient org, where the highest volume of experiments happens, and serve the whole company. You will own assignment, exposure, and the experiment data pipelines. You will work closely with Data Science (who own statistical methodology) and with the teams who own our event tracking and metric definitions.

Who You Are

We are looking for a Staff‑level engineer who wants their impact measured by what other teams can now do. You think in systems, you are uncomfortable with numbers you cannot explain, and you raise the bar for the people around you.

• You have owned an experimentation or feature flagging stack end to end — accountable for whether the results were correct.


• You have built the parts that don't come out of the box: assignment that persists correctly, exposure that reflects what a user actually saw, identity resolved across sessions and devices, and diagnostics that catch a broken experiment early.


• You are fluent enough in statistics to be a real partner to data scientists — able to tell the difference between a result that is weak and one that is invalid.


• You have debugged hard measurement bugs: traffic that split unevenly, users who ended up in both arms, effects that vanished once you looked at who was actually exposed, identity that broke between anonymous and logged‑in sessions.


• You have built a program and not only a platform — measurably raising how well an organization experiments through defaults, templates, review, and teaching, not only through code.


• You have made a build‑versus‑buy call on a platform and lived with it, reasoning about vendor risk and where a warehouse‑native approach beats a hosted one.


• You have landed a migration on teams that did not ask for one, by making the new path easier than the old path rather than by mandate.


• You use AI as genuine leverage in your work and have clear opinions about where it must not be trusted without a human.


• You have driven technical direction beyond your own team through design documents, reviews, and planning cycles, and you regularly mentor senior engineers.


• You are willing to flex across the stack — this role touches backend services, front‑end rendering, CDN behavior, and the data warehouse.


• Experience with multi‑sided marketplaces, growth or search and ranking systems, or healthcare is a plus, though none is required.

Compensation

The expected base pay range for this position is $265,000–$331,000, 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.

Medical, dental, vision, HSA/FSA, 401(k) including match (for 2027!), Carrot Fertility reimbursement, and paid parental, medical, and caregiver leave.

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.

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 unofficial channel, please do not share any information and report it as spam.

Is this Staff Software Engineer role at Headway fully remote? The job posting does not explicitly state remote or in‑office, but it is a US‑only position (E‑Verify required) with no specific office location mentioned. Candidates should confirm the remote policy directly with Headway's recruiter. What is the salary range for this Staff Software Engineer role? The expected base pay range is $265,000–$331,000 annually, depending on qualifications, experience, and geographic location. The role may also be eligible for an equity grant. What experimentation tools does Headway currently use? Headway currently runs LaunchDarkly and Statsig for experimentation and feature flagging, alongside dbt and Snowflake for analytics. Part of this role involves evaluating and potentially consolidating that architecture. Do I need healthcare or marketplace industry experience to apply? No — experience with multi‑sided marketplaces, growth systems, or healthcare is listed as a plus but explicitly stated as not required. The core requirements focus on experimentation platform ownership and statistical fluency. What benefits does Headway offer for this role? Benefits include medical, dental, and vision coverage, HSA/FSA, 401(k) with employer match, Carrot Fertility reimbursement, and paid parental, medical, and caregiver leave.

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