[All remote jobs](https://jobicy.com/jobs.md)[![Headway.co logo](https://jobicy.com/data/server-nyc0409/galaxy/mercury/2021/12/068391a61855fb604bca051cafe3c510.jpeg)](https://jobicy.com/company/headway.md)[Headway.co](https://jobicy.com/company/headway.md) # Staff Software Engineer – Experimentation AI Summary Headway is seeking a Staff Software Engineer to own and evolve its company-wide experimentation and feature-flagging platform. The role combines hands-on platform engineering with technical product leadership across assignment, exposure tracking, identity resolution, data pipelines, and experiment diagnostics. The engineer will evaluate and consolidate tools such as LaunchDarkly and Statsig while enabling sophisticated market-level and long-running tests for a multi-sided healthcare marketplace. Success requires strong statistical judgment, cross-functional partnership with Data Science, and the ability to improve experimentation practices through standards, documentation, reviews, and mentoring. The stack includes Python, TypeScript, FastAPI, React, Snowflake, dbt, AWS, Kafka, and Datadog.[Apply for this job](#job-application)[View company](https://jobicy.com/company/headway.md)ShareRemote from[USA](https://jobicy.com/job-region/usa.md)SalaryUSD 265k–331k / yrDepartment[Software Engineering](https://jobicy.com/categories/engineering.md)EmploymentFull TimeExperienceSeniorPublished7 Nov 2026Apply before7 Dec 2026Listing views49Application actions4Application toolkit ## Make your next move. Prepare your resume, explore your fit, and draft a cover letter for this opportunity. Opportunity details ## About this role. 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 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 at Headway is a small but mighty team using technology to build that future (and have a fun time while doing it!). 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 iteration * 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 * Experimentation & Analytics: LaunchDarkly, Statsig, dbt, Snowflake * Datastores: Postgres, Redis * Infrastructure: AWS (Fargate, ECS, S3, and more), Cloudflare, Spark and Kafka * Monitoring: Datadog, PagerDuty, Sentry * 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 the second principle on the list above, 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 the 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. You will 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. You will also 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. We need to hold groups out for long stretches to understand real long-term impact. These capabilities are well understood in the industry and we have not built them yet, and they are the ones our business needs next. 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, which means 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. Trustworthy results are shared ownership. You will own assignment, exposure, and the experiment data pipelines, which are the parts of the chain that are engineering problems. You will work closely with Data Science, who own statistical methodology, and with the teams who own our event tracking and metric definitions, because a number is only as trustworthy as the weakest link in that chain. 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 rather than only used one. Whether you built it from first principles or built the missing pieces on top of a vendor matters far less to us than having been accountable for whether the results were correct. * You have built the parts that do not come out of the box: assignment that persists correctly, exposure that reflects what a user actually saw, identity resolved across sessions and devices, or the diagnostics that catch a broken experiment early. * You are fluent enough in the statistics to be a real partner to data scientists. You can tell the difference between a result that is weak and a result that is invalid, and you can hold your position on a measurement question with someone who does this full time. * You have debugged the hard class of 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. You have measurably raised 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. You can reason about vendor risk and about 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 you 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. ### Comprehensive benefits: 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. Headway participates in E-Verify. To learn more, click [here.](https://www.e-verify.gov/sites/default/files/everify/posters/EVerifyParticipationPoster.pdf) 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](https://jobicy.com/company/headway.md). 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](http://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. Show more [Apply now >](https://jobicy.com/jobs/159641-staff-software-engineer-experimentation.md) * ![Upload CV](data:image/svg+xml;base64,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) ### Upload your resume now To unlock remote work opportunities and be discovered by global employers. This job listing has been manually reviewed by the Jobicy Trust & Safety Team for compliance with our posting guidelines, including verification of the company's legitimacy, accuracy of job details, clarity of remote work policy, and absence of misleading or fraudulent content. ## Role DNA A quick view of the complexity, pace, ownership and collaboration implied by the job description. ### Job Complexity 5/5EasyHard ### Pace & Pressure 5/5RelaxedFast-paced ### Autonomy Level 5/5GuidedFull ownership ### Communication Load 5/5IndependentCollaborative AI insightЭто staff-уровень с широкой ответственностью за критичную платформу, корректность измерений и техническую стратегию для многих команд. Требуются глубокие навыки распределённых систем, экспериментальной инфраструктуры, статистики и организационного влияния. ## Salary analysis Estimated compensation compared with the broader US market for similar roles. Estimated job median (per year)Market rate$298,000US market range (per year)$250k–$360k0$396.00k AI insightРаботодатель прямо указывает годовой базовый диапазон $265,000–$331,000 USD; медианная точка диапазона составляет $298,000 в год. Оценочный рыночный диапазон для staff-инженера по экспериментальным платформам в США составляет $250,000–$360,000 в год и не включает equity или бонусы. ## Core skills Skills and capabilities most closely associated with this opportunity. [Experimentation platforms](https://jobicy.com/jobs?search_keywords=Experimentation%20platforms.md)[Feature flagging](https://jobicy.com/jobs?search_keywords=Feature%20flagging.md)[A/B testing](https://jobicy.com/jobs?search_keywords=AB%20testing.md)[Statistical analysis](https://jobicy.com/jobs?search_keywords=Statistical%20analysis.md)[Python](https://jobicy.com/jobs?search_keywords=Python.md)[TypeScript](https://jobicy.com/jobs?search_keywords=TypeScript.md)[FastAPI](https://jobicy.com/jobs?search_keywords=FastAPI.md)[React](https://jobicy.com/jobs?search_keywords=React.md)[Snowflake](https://jobicy.com/jobs?search_keywords=Snowflake.md)[dbt](https://jobicy.com/jobs?search_keywords=dbt.md)[AWS](https://jobicy.com/jobs?search_keywords=AWS.md)[Kafka](https://jobicy.com/jobs?search_keywords=Kafka.md)[Identity resolution](https://jobicy.com/jobs?search_keywords=Identity%20resolution.md)[Data pipelines](https://jobicy.com/jobs?search_keywords=Data%20pipelines.md)[Technical leadership](https://jobicy.com/jobs?search_keywords=Technical%20leadership.md) Sample interview questionsHow would you design a durable experiment-assignment system that works across anonymous and authenticated sessions?I would define a stable subject model and deterministic bucketing strategy, record assignment with a versioned experiment configuration, and link anonymous identifiers to authenticated identities through an audited merge process. I would preserve assignment history and expose clear APIs so downstream systems can consistently retrieve the same treatment. What checks would you build to detect an invalid or broken experiment before results are reviewed? I would automate preflight and runtime checks for sample-ratio mismatch, assignment and exposure consistency, duplicate or cross-arm enrollment, event-volume anomalies, missing metrics, and identity-resolution failures. Alerts should distinguish between warnings and conditions that automatically pause or invalidate an experiment. How would you evaluate whether to retain LaunchDarkly and Statsig, consolidate vendors, or build internal capabilities? I would inventory current use cases, reliability gaps, cost, data ownership, latency, warehouse integration, migration risk, and required capabilities such as market-level experiments. I would retain vendor functionality where it is differentiated and reliable, while building internal primitives where Headway needs control, correctness, or workflows the vendors cannot provide. How would you approach a market-level experiment in a multi-sided marketplace? I would define the unit of randomization and account for interference between therapists and patients, then select geographically distinct and sufficiently comparable markets. The analysis plan would include pre-period matching, long observation windows, guardrail metrics, and methods appropriate for clustered assignment rather than treating individual observations as independent. Describe how you would raise experimentation quality across teams without becoming a bottleneck. I would make the correct path the easiest path through opinionated templates, self-service tooling, automated validation, clear documentation, and lightweight review for higher-risk tests. 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