Drimva

Headway

Staff Software Engineer - Experimentation

$265K–$331K

Remote +3 · Remote · Staff · Full-time · Posted Aug 10, 2026

Location
Remote
San Francisco, CA
Seattle, WA
New York City

About the job

Own and evolve Headway’s company-wide experimentation platform and program, enabling teams to run trustworthy user- and market-based tests.

What you'll do

  • Design and build experiment assignment, exposure tracking, identity resolution, and experiment data pipelines; evaluate and consolidate the feature-flagging stack.
  • Develop capabilities for market-based and long-term testing, and use AI to validate experiment setups and detect failures.
  • Improve company-wide experimentation practices through roadmaps, defaults, reviews, documentation, and education; partner with Data Science and other teams.

What they ask for

  • End-to-end ownership of an experimentation or feature-flagging stack, including accountability for result correctness.
  • Experience building custom experimentation capabilities such as assignment, exposure measurement, identity resolution, or diagnostics, and debugging measurement issues.
  • Statistical fluency to partner with data scientists and assess whether results are weak or invalid.
  • Experience building an organizational experimentation program, making platform build-versus-buy decisions, landing migrations, and driving technical direction while mentoring engineers.

Nice to have

  • Experience with multi-sided marketplaces, growth or search and ranking systems, or healthcare.
  • Use of AI as a work tool, with clear judgment about where human oversight is needed.

Pay

$265,000-$331,000 USD base salary

Tools

LaunchDarkly, Statsig, Python 3, TypeScript, dbt, Snowflake, Postgres, AWS

AI focus

Use AI in experiment workflows, including pre-launch setup validation and automated detection of broken experiments; apply human judgment where AI should not be trusted.

Model-written summary · the original posting is authoritative

First seen Oct 27, 2026 · Last verified Nov 5, 2026 (UTC)