Senior Machine Learning Engineer at Headway

You are a seasoned machine learning expert with over five years of applied experience and a deep background in ranking, relevance, or personalization systems. Y

Work type: remote

Location: New York, New York, United States; San Francisco, California, United States; Seattle, Washington, United States

Salary: $218,500 – $273,125/yr

Type: Full-time

Summary

You are a seasoned machine learning expert with over five years of applied experience and a deep background in ranking, relevance, or personalization systems. You have spent at least three years hands-on with modeling and know how to move products from a prototype into a reliable production environment. **What makes it worth a look...** Headway offers a remote-first culture with an impressive base salary range of $218,500 to $273,125 per year plus equity. You get unique perks like therapy reimbursement, a home office stipend, and a week-long company break in December. **You might be a good fit if you...** * Are proficient in Python and tools like TensorFlow, PyTorch, or CatBoost. * Have experience running A/B experiments and selecting the right metrics for user-facing products. * Can manage the full model lifecycle from offline evaluation to production monitoring. * Understand modern retrieval techniques like vector search and semantic embeddings.

Job Description

Headway’s mission is a big one – to build a new mental health care system everyone can access. We’ve built technology that helps people find great therapists with the first software-enabled national network of providers accepting insurance.

1 in 4 people in the US have a treatable mental health condition, but the majority of providers don’t accept insurance, making therapy too expensive for most people. Headway is building a new mental healthcare system that everyone can access by making it easy for therapists to accept insurance and scale their practice.

Headway was founded in 2019. Since then, we’ve grown into a diverse, national network of over 60,000 mental healthcare providers across all 50 states who run their practice on our software and have served over 1 million patients. We’re a Series D company with over $325m in funding from a16z (Andreessen Horowitz), Accel, GV (formerly Google Ventures), Spark Capital, Thrive Capital, Forerunner Ventures and Health Care Service Corporation.

We want your time here to be the most meaningful experience of your career. Join us, and help change mental healthcare for the better.About the team

The Ranking & Relevance team’s mission is to help every patient find the right provider for their needs. We are building the matching system that powers this connection, from search and discovery to ranking and personalization. Our goal is to combine cutting-edge machine learning with a deep understanding of patient and provider experience.

About the role

We are looking for a Senior Machine Learning Engineer to be a core contributor to Headway's ranking and relevance systems. You will design, build, and ship ML models that determine how patients discover and connect with therapists — using search, recommendation, and personalization techniques to improve matching quality across the care journey.

In this role, you will work with significant autonomy on scoped problem areas, contribute to technical direction, and collaborate closely with product, engineering, and data science to drive measurable outcomes for patients and providers.

## What you’ll do

At Headway, one of our most important challenges is ensuring that patients find the right therapist quickly and effectively. We are investing deeply in search, ranking, and relevance systems powered by machine learning. As a Senior Machine Learning Engineer, you will focus on:

• Matching and ranking: Build and iterate on ML models that power how patients discover and connect with providers — from candidate generation to final ranking.

• Personalization: Leverage patient signals, provider attributes, and outcomes data to improve matching accuracy and relevance over time.

• Model development end-to-end: Own the full lifecycle of models you build — from offline evaluation and experimentation to production deployment and monitoring.

• Experimentation: Design and analyze A/B tests, define the right offline proxies and online metrics, and translate results into product decisions.

• Cross-functional collaboration: Partner with product managers, software engineers, and data scientists to scope problems, align on success metrics, and ship improvements that move the needle for patients.

• Raising the bar: Contribute to ML best practices on the team — through code reviews, documentation, and sharing what you learn from the systems you build.

• You have 5+ years of experience in applied ML roles, with at least 3 years of meaningful hands-on modeling work in ranking, relevance, recommendations, search, or personalization.

• You are fluent in Python and experienced with ML frameworks such as TensorFlow, PyTorch, Scikit-learn, or CatBoost.

• You have taken ML models from prototype to production and understand what it takes to make them reliable, maintainable, and performant at scale.

• You are comfortable designing and running A/B experiments, selecting appropriate metrics, and interpreting results with rigor.

• You bring product intuition alongside technical depth — you care about making the patient experience meaningfully better, not just improving an offline metric.

• You work well in collaborative, cross-functional environments and can communicate technical tradeoffs clearly to non-ML stakeholders.

• Experience with search, discovery, matching systems or consumer facing personalization.

• Familiarity with modern retrieval techniques (vector search, embeddings, semantic search).

• Exposure to ML infrastructure such as feature stores, model monitoring, and retraining pipelines.

• Experience with Metaflow, SageMaker, and Outerbounds.

• Background in healthcare, marketplace, or other B2C domains where user-provider or user-product fit is the core product problem.

After you apply to Headway, here are some details of what to expect during the interview process.

1. Initial screen: You’ll connect with someone in recruiting so you can learn more about the team, Headway’s mission and exciting growth, and we can get a better idea of your background.

2. First round: You’ll meet with an engineer on the team to do some live coding and learn more about the engineering team.

3. Final rounds: You’ll meet several more team members for technical and non-technical interviews and leave with a fuller picture of what it’s like to work at Headway.

4. References and the offer:Our favorite part of the process. We’ll send over all of the details, including specifics on employee equity, and congratulatory messages from excited future team members.

Compensation and Benefits:

The expected base pay range for this position is $218,500 - $273,125, based on a variety of factors including qualifications, experience, and geographic location. In addition to base salary, this role may be eligible for an equity grant, depending on the position and level.

We are committed to offering a comprehensive and competitive total rewards package, including robust health and wellness benefits, retirement savings, and meaningful ownership opportunities through equity. Compensation decisions are made holistically, ensuring fairness and alignment with market benchmarks while recognizing individual contributions and potential.

• Benefits offered include:

• 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

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