Staff Software Engineer - Experimentation

Salary: $265,000 - 331,000 per year Requirements:

• We need someone who has owned an experimentation or feature-flagging stack end to end, with accountability for result quality rather than only using an existing tool.
• We are looking for experience building the non-obvious pieces, such as persistent assignment, accurate exposure tracking, cross-device identity resolution, or early warning diagnostics for broken tests.
• You should be fluent in statistics well enough to partner closely with data scientists and distinguish weak findings from invalid ones.
• We expect hands-on experience debugging difficult measurement issues, including uneven traffic splits, users appearing in both variants, exposure-related effect loss, and identity breakage across anonymous and signed-in sessions.
• You should have built not just a platform, but also a program that improved experimentation through defaults, templates, review processes, and education.
• We need someone who has made build-versus-buy decisions for a platform and can weigh vendor risk against warehouse-native approaches.
• You should have successfully led migrations for teams that were not initially asking for them by making the new solution easier to adopt.
• We want someone who uses AI as practical leverage and knows where human judgment is still required.
• You should have influenced technical direction beyond your immediate team through design docs, reviews, and planning, and have experience mentoring senior engineers.
• You must be comfortable working across the stack, including backend services, frontend rendering, CDN behavior, and the data warehouse.
• Experience in multi-sided marketplaces, growth or search/ranking systems, or healthcare is a plus, though not required.

• We will have you own the experimentation platform that powers how we run tests across the company.
• You will design and build the core mechanics, including assignment logic, exposure tracking, identity resolution, and experiment data pipelines.
• You will help determine our long-term experimentation and feature-flag architecture, including evaluating and potentially consolidating our current vendor stack.
• You will apply AI to improve workflows such as experiment setup validation and automated detection of broken experiments.
• You will extend our experimentation system into market-based testing for a multi-sided marketplace.
• You will support tests that span entire geographic markets and long time horizons to measure lasting impact.
• You will shape the experimentation program as well as the platform by improving defaults, review standards, documentation, and training.
• You will collect needs from multiple teams, prioritize them into a roadmap, and make clear tradeoffs and decisions.
• You will work from within the Patient org while serving the needs of the wider company.
• You will partner closely with Data Science on statistical methodology and with teams responsible for event tracking and metric definitions.
• You will own the engineering parts of trustworthy measurement across assignment, exposure, and data pipelines.

• AI
• Backend
• Data Warehouse
• Frontend
• Support
• Spark
• AWS
• Cloud
• Datadog
• Exposed
• FastAPI
• GitHub
• Kafka
• LESS
• PagerDuty
• Product Manager
• Python
• React
• Redis
• Sentry
• Slack
• Snowflake
• TypeScript
• dbt

More:

We are Headway, and our mission is to make mental healthcare accessible by fixing the insurance barriers that keep therapy too expensive for many people. We have automated the administrative burden around credentialing, claims, and payment reconciliation, and today more than 75,000 providers across all 50 states use our software to serve over 1 million patients. We are a Series D company backed by investors including a16z, Accel, and Spark Capital, with more than $325M in funding. Our engineering team is small but high impact, guided by a mission-first mindset, rapid shipping and learning, product thinking in everything we build, and a culture of trust and psychological safety. This Staff Software Engineer role sits in our Patient org and offers a base salary range of $265,000-$331,000, with possible equity, plus a comprehensive benefits package that includes medical, dental, and vision coverage, 401K, HSA/FSA, therapy reimbursement, parental leave, flexible PTO, professional development, and more.

last updated 33 week of 2026