Staff Software Engineer – Experimentation

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🔥 0 minutes ago

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

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

💵 $265k - $331k / year

⏰ Full Time

🔴 Lead

🧑‍💻 Full-stack Engineer

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Headway

WebsiteLinkedInAll Job Openings

501 - 1000 employees

Founded 2019

🏥 Healthcare

🏪 Marketplace

☁️ SaaS

💰 $100M Series D - Headway on 2024-07

Healthcare • Marketplace • SaaS

Headway is a healthcare technology company (Therapymatch, Inc. ) that operates an insurance-native marketplace connecting people with licensed mental health providers — therapists and psychiatrists — for in-person and online care. Headway matches users with providers by specialty, location, and insurance coverage, handles insurance verification and billing, and offers tools for providers (provider portal and an insurance-native EHR) to reduce administrative burden. The platform partners with 100+ insurance plans, supports many languages, and emphasizes affordable, in-network mental health care.

📋 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