Staff Software Engineer — Experimentation Platform

Headway; New York, Northern (NY, KY); Hybrid; USD 265,000 - 331,000; Full time

Benefits offered by this job

Equity compensation

Medical, Dental, Vision coverage

HSA / FSA

401K

Work-from-Home Stipend

Therapy Reimbursement

16-week parental leave

Holiday break

Flexible PTO

EAP

Training and development

Job summary

Headway is seeking a Staff Software Engineer to own the experimentation platform that powers how patients find therapists, how providers are onboarded, and how AI features are validated. You will design core primitives for experiment assignment, exposure tracking, and identity across devices, while consolidating the feature-flagging stack and ensuring trustworthy results across teams.

You will also shape the broader program, including defaults, reviews, and educational resources, partnering with

Qualifications

• Experience owning a complete experimentation/feature-flagging stack.
• Ability to design end-to-end experiment data pipelines (exposure, identity, tracking).
• Fluent in statistics; partner with data scientists on results interpretation.
• Proven ability to mentor engineers and guide cross-team initiatives.

Responsibilities

• Own the experimentation platform powering multi-team tests and AI workflows.
• Define and evolve the defaults, reviews, and templates that enable company-wide trustworthy experiments.
• Lead architecture for assignment, exposure, identity across sessions/devices, and data pipelines.
• Collaborate with Data Science and analytics teams on metric definitions and event tracking.

Skills

Experimentation stack ownership

Platform design & data pipelines

A/B testing & feature flags

Statistical reasoning & collaboration

Cross-team leadership

AI integration into workflow

Migration & modernization experience

Tools

LaunchDarkly

Statsig

SQL/DBT workflows

Job description

Headway is seeking a Staff Software Engineer to own the experimentation platform that powers how patients find therapists, how providers are onboarded, and how AI features are validated. You will design core primitives for experiment assignment, exposure tracking, and identity across devices, while consolidating the feature-flagging stack and ensuring trustworthy results across teams.

You will also shape the broader program, including defaults, reviews, and educational resources, partnering with