Staff Software Engineer - Experimentation

The role

You will own the experimentation platform and program at Headway. You will design core primitives for user assignment and exposure, decide the long-term feature flagging stack, and evolve capabilities for market-based testing.

What you will do

• Own the experimentation platform and program
• Design and build core primitives including user assignment and exposure
• Recognize the same person across devices and between browsing anonymously and signing in
• Evaluate and consolidate the long-term experimentation and feature flagging stack
• Make AI a part of the workflow for validating experiments and catching broken ones
• Evolve experimentation capabilities to expand into market-based testing
• Gather needs from teams and sequence them into a roadmap
• Act as a technical product manager for the platform
• Own assignment, exposure, and experiment data pipelines
• Mentor senior engineers and drive technical direction through design documents and reviews

Required qualifications

• Owned an experimentation or feature flagging stack end to end
• Built parts that do not come out of the box like assignment, exposure, identity resolution, or diagnostics
• Fluent in statistics to partner with data scientists
• Debugged measurement bugs like uneven traffic splits or identity issues
• Built a program through defaults, templates, review, and teaching
• Made build versus buy calls on a platform
• Landed a migration on teams by making the new path easier
• Use AI as leverage in work
• Driven technical direction through design documents, reviews, and planning cycles
• Regularly mentor senior engineers
• Willing to flex across the stack including backend, frontend, CDN, and data warehouse

Nice to have

• Experience with multi-sided marketplaces
• Experience with growth or search and ranking systems
• Experience with healthcare

Benefits

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

About the company

Headway is a Series D company with $325M+ in funding building a new mental healthcare system. They provide software for over 90,000 providers to run their practices and serve over 2.6 million patients.