Staff Software Engineer — Experimentation Platform

Headway; New York (NY); On-site; USD 265,000 - 331,000; Full time

Benefits offered by this job

Medical benefits

Dental & Vision

HSA/FSA

401(k) match

Fertility reimbursement

Parental leave

Job summary

Headway is building a new mental healthcare system that scales with technology. We are seeking a Staff Software Engineer to own how Headway runs experiments, from assignment to exposure tracking, and to define the long-term experimentation and feature-flagging stack.

You will work across the platform, integrating AI into the workflow and enabling trusted results for a multi-team environment. You will lead design decisions, mentor engineers, and collaborate with Data Science to ensure rigorous

Qualifications

• Experience owning an experimentation or feature-flagging stack end to end.
• Built parts that do not come out of the box: assignment persistence, exposure accuracy, identity resolution across sessions.
• Fluent in statistics to partner with data scientists and assess measurement questions.

Responsibilities

• Own the platform that runs experiments across teams.
• Design and build core primitives for experiment assignment, exposure tracking, and cross-device identity.
• Define and manage the long-term experimentation and feature-flagging stack architecture (LaunchDarkly, Statsig).
• Incorporate AI into workflows, validate experiments, and catch broken experiments automatically.

Skills

Experimentation ownership

Feature flags

End-to-end ownership

AI in workflow

Tools

LaunchDarkly

Statsig

dbt

Snowflake

Postgres

Redis

AWS

S3

Kafka

Job description

Headway is building a new mental healthcare system that scales with technology. We are seeking a Staff Software Engineer to own how Headway runs experiments, from assignment to exposure tracking, and to define the long-term experimentation and feature-flagging stack.

You will work across the platform, integrating AI into the workflow and enabling trusted results for a multi-team environment. You will lead design decisions, mentor engineers, and collaborate with Data Science to ensure rigorous