Staff Software Engineer - Experimentation
Headway · Remote · Remote · San Francisco, CA · Seattle, WA · New York City ·
COMPENSATION
$265k – $331k
Listed on the employer's job board (Ashby)
- Staff level role
- Fully remote (US)
- Python + TypeScript
- Experimentation focus
- Equity compensation
You will lead the technical strategy for Headway’s experimentation infrastructure, serving over 85,000 providers and millions of patients. The role requires building robust assignment logic, exposure tracking, and identity resolution while integrating AI for workflow validation. You will act as a technical product manager for the platform, setting defaults and educating teams to ensure trustworthy results.
What you'll do
- Design core primitives for user assignment and exposure tracking
- Evaluate and consolidate the long-term feature flagging stack
- Integrate AI to validate setups and detect broken experiments
- Expand capabilities to support market-based and geographic testing
- Establish documentation, reviews, and education for company-wide use
- Collaborate with Data Science on statistical methodology and metrics
- Migrate teams to new systems by improving ease of use
What you'll need
- Experience owning an experimentation or feature flagging stack end-to-end
- Ability to build custom assignment, exposure, and identity resolution logic
- Fluency in statistics to partner effectively with data scientists
- Track record debugging complex measurement bugs and traffic splits
- Experience building organizational programs through defaults and teaching
- Proven ability to make and manage build versus buy decisions
- Willingness to work across backend, frontend, CDN, and data warehouse layers
Nice to have
- Experience with multi-sided marketplaces
- Background in growth or search and ranking systems
- Prior work in the healthcare industry
Stack
- Python 3
- TypeScript
- FastAPI
- SQLAlchemy
- React
- Remix
- LaunchDarkly
- Statsig
- dbt
- Snowflake
- Postgres
- Redis
- AWS
- Cloudflare
- Kafka
- Datadog
How you'll work
- Fully remote position
- Based in the United States
- Flexible PTO policy
- 13 paid holidays plus year-end break
What you get
- Base salary range $265k-$331k
- Equity compensation grants
- Medical, Dental, and Vision coverage
- HSA and FSA options
- 401K retirement plan
- Work-from-home stipend
- Therapy reimbursement
- 16-week parental leave
- Fertility benefits via Carrot
- Training and professional development budget