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Staff Software Engineer - Experimentation
Headway
Remote · United States$22,083–27,583 gross/mofull-timeHeadway Careers
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.
Responsibilities
- 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.
- 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!).
- 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.
- 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 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 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.
Languages
- Work format
- Remote
- Seniority
- Senior
- Posted
- 10 Aug 2026
- Last verified
- In the last 5 days
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