Staff Software Engineer – Experimentation

🕒 August 10

🏄 California, New York, +1 more states – Remote

🏄 California – Remote 🗽 New York – Remote ☕ Washington – Remote

💵 $265k - $331k / year

⏰ Full Time

🔴 Lead

🧑‍💻 Full-stack Engineer

🦅 H1B Visa Sponsor

This company has sponsored H1B visas in the past.

👻 Ghost score 11%

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Headway

WebsiteLinkedInAll Job Openings

201 - 500 employees

Founded 2019

🛡️ Insurance

💼 Consulting

📦 Logistics

Insurance • Consulting • Logistics

Headway is a platform that connects individuals with mental health providers, helping them find the right fit according to their needs and insurance coverage. By partnering with numerous insurance providers, Headway ensures that users can access mental health care affordably. It offers both in-person and virtual care options, and manages the payment and billing processes for a hassle-free experience. The platform's aim is to simplify the search and access to therapy and psychiatric support for users, allowing them to focus on their mental health without the administrative burdens.

📋 Description

• Own the platform Headway uses to run experiments across the company • Design and build experimentation primitives for user assignment, exposure recording, and cross-device identity resolution • Evaluate and potentially consolidate the LaunchDarkly and Statsig experimentation and feature-flagging architecture • Integrate AI into experiment setup validation and automatic detection of broken experiments • Expand experimentation capabilities to market-based testing, geographic-market tests, and long-term holdout groups • Establish defaults, review processes, documentation, and education to improve company-wide experimentation • Gather needs from teams, sequence them into a roadmap, and manage the platform’s technical product direction • Own assignment, exposure, and experiment data pipelines • Collaborate with Data Science on statistical methodology and with event-tracking and metric-definition teams • Drive technical direction through design documents, reviews, and planning cycles • Mentor senior engineers • Work across backend services, front-end rendering, CDN behavior, and the data warehouse

🎯 Requirements

• Experience owning an experimentation or feature-flagging stack end to end • Experience building assignment persistence, exposure tracking, cross-session and cross-device identity resolution, or experiment diagnostics • Fluency in statistics sufficient to partner with data scientists and assess result validity • Experience debugging measurement issues including uneven traffic splits, users in both experiment arms, exposure discrepancies, and broken identity resolution • Experience improving organizational experimentation through defaults, templates, review, and teaching • Experience making build-versus-buy platform decisions and evaluating vendor risk and warehouse-native approaches • Experience leading migrations by making the new path easier than the old path • Experience using AI as leverage with clear boundaries for human oversight • Experience driving technical direction through design documents, reviews, and planning cycles • Experience mentoring senior engineers • Willingness to work across backend services, front-end rendering, CDN behavior, and data warehouse systems • Experience with multi-sided marketplaces, growth or search and ranking systems, or healthcare is a plus, not required • Proficiency with Python 3 and TypeScript • Experience with FastAPI, SQLAlchemy, React, Remix, LaunchDarkly, Statsig, dbt, Snowflake, Postgres, Redis, AWS, Cloudflare, Spark, Kafka, Datadog, PagerDuty, Sentry, and GitHub

🏖️ 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 • Holiday Break during the week between December 25th and December 31st • Flexible PTO • Employee Assistance Program (EAP) • Training and professional development • Robust health and wellness benefits • Meaningful ownership opportunities through equity

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