Staff Software Engineer - Experimentation
Own the company-wide experimentation platform, building reliable assignment, exposure, identity, data-pipeline, and market-testing capabilities while raising experimentation standards across teams. The role requires staff-level technical leadership, statistical fluency, and experience operating experimentation or feature-flagging systems.
About the job
Responsibilities
- Own Headway’s experimentation platform, including user assignment, exposure tracking, identity resolution across devices and sessions, and experiment data pipelines.
- Evaluate and consolidate the LaunchDarkly and Statsig experimentation and feature-flagging stack.
- Build capabilities for market-based testing, including geographic-market experiments and long-term holdout groups for a multi-sided marketplace.
- Add AI-assisted workflows to validate experiment setup and detect broken experiments automatically.
- Establish platform defaults, review processes, documentation, templates, and education that improve experimentation across the company.
- Gather needs from teams, define and sequence a roadmap, and provide technical product direction for the experimentation platform.
- Partner with Data Science on statistical methodology and with event-tracking and metrics teams to ensure trustworthy measurement.
- Drive technical direction through design documents, reviews, and planning cycles.
- Mentor senior engineers and flex across backend services, frontend rendering, CDN behavior, and data warehouse systems.
Requirements
- Staff-level software engineering experience with hands-on technical leadership.
- End-to-end ownership of an experimentation or feature-flagging stack, whether built internally or extended on top of a vendor.
- Experience building experimentation primitives such as persistent assignment, accurate exposure tracking, cross-session and cross-device identity resolution, or experiment diagnostics.
- Strong statistical fluency and the ability to distinguish weak results from invalid results while partnering with data scientists.
- Experience diagnosing measurement issues such as uneven traffic splits, users appearing in multiple experiment arms, exposure mismatches, and broken identity resolution.
- Experience improving organizational experimentation through defaults, templates, reviews, and education.
- Experience making build-versus-buy decisions for platforms, assessing vendor risk, and evaluating warehouse-native approaches.
- Experience leading migrations by making the new path easier than the old one.
- Ability to use AI effectively while identifying situations that require human oversight.
- Willingness to work across the stack, including backend, frontend, CDN, and data warehouse systems.
Nice-to-haves
- Experience with multi-sided marketplaces, growth systems, search and ranking systems, or healthcare.
Technologies
- Python 3, TypeScript, FastAPI, SQLAlchemy, React, Remix
- LaunchDarkly, Statsig, dbt, Snowflake
- PostgreSQL, Redis
- AWS, Fargate, ECS, S3, Cloudflare
- Spark, Kafka
- Datadog, PagerDuty, Sentry
- GitHub
Compensation and Benefits
- Expected base pay: $265,000–$331,000.
- Compensation varies based on qualifications, experience, and geographic location.
- May be eligible for an equity grant.
- Comprehensive total rewards package, including health benefits.
Skills
Python, TypeScript, FastAPI, Sqlalchemy, React, Remix, Launchdarkly, Statsig, dbt, Snowflake, Postgres, Redis, AWS, Kafka, Cloudflare
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