Staff Software Engineer - Experimentation

Role Description

We are looking for a Staff Software Engineer to own how Headway runs experiments. "Ship small, learn fast" is the second principle on the list above, and experimentation is how we actually do it:

• Eleven teams have run hundreds of experiments deciding how patients find a therapist.
• How quickly new providers get up and running.
• Whether our AI products are working.
• How we collect the clinical outcomes data that proves care is effective.

You will own the platform all of that runs on. This is a hands-on technical leadership role with unusually wide reach. You will:

• Design and build the core primitives, including how users are assigned to experiments.
• Record what someone actually saw and recognize the same person across devices.
• Decide what our long-term experimentation and feature flagging stack should be.
• Make AI a real part of the workflow.
• Evolve our experimentation capabilities to expand into market-based testing.
• Gather needs from teams and sequence them into a roadmap.
• Act as part technical product manager for your own platform.

You will sit in the Patient org, where the highest volume of experiments happens, and serve the whole company. Trustworthy results are shared ownership. You will own:

• Assignment, exposure, and the experiment data pipelines.
• Work closely with Data Science and other teams on event tracking and metric definitions.

Qualifications

• Experience as a Staff level engineer with measurable impact on other teams.
• Fluency in systems thinking and statistical analysis.
• Experience owning an experimentation or feature flagging stack end to end.
• Ability to debug complex measurement bugs.
• Experience building a program that improves organizational experimentation.
• Experience making build versus buy decisions on platforms.
• Experience driving technical direction beyond your own team.
• Willingness to flex across the stack, touching backend services, front end rendering, CDN behavior, and the data warehouse.
• Experience with multi-sided marketplaces, growth, or healthcare is a plus.

Requirements

• Experience building parts that do not come out of the box.
• Ability to reason about vendor risk and platform choices.
• Experience using AI as leverage in work.
• Ability to mentor senior engineers.

Benefits

• Equity compensation
• Medical, Dental, and Vision coverage
• HSA / FSA
• 401K
• Work-from-Home Stipend
• Therapy Reimbursement
• 16-week parental leave for eligible employees
• Carrot Fertility annual reimbursement and membership
• 13 paid holidays each year as well as a Holiday Break during the week between December 25th and December 31st
• Flexible PTO
• Employee Assistance Program (EAP)
• Training and professional development