Staff Machine Learning Engineer

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 Staff Machine Learning Engineer to lead the development of Headway’s ranking and relevance models. You will design and build the systems that decide how patients and providers are matched, using search, recommendation, and personalization to help patients through their care journey. You will set technical direction, build the initial stack, and mentor future ML teammates.

What you’ll do

At Headway, we have built the largest network of therapists who accept insurance in the country. One of our most important challenges is ensuring that patients find the right therapist for them quickly and effectively. To do this, we are investing deeply in search, ranking, and relevance systems powered by machine learning. As a Staff Machine Learning Engineer on the Patient team, you will focus on:

• Matching and ranking: Design and scale ML models that power how patients discover and connect with providers.
• Personalization: Use patient signals, provider attributes, and outcomes data to improve matching accuracy.
• ML infrastructure: Establish the foundation for experimentation, model training, deployment, and monitoring across Headway.
• Mentorship and technical leadership: Guide junior ML engineers and data scientists as the team grows, setting the bar for ML practices at Headway.
• Cross-functional impact: Partner with product, engineering, and data science to define success metrics, design A/B experiments, and influence product strategy.

Who you are

• You have 6+ years of experience in applied ML roles, with at least 1 year working on ranking, relevance, search, or recommender systems.
• You are fluent in Python and have experience with ML frameworks (TensorFlow, PyTorch, Scikit-learn, CatBoost, etc.).
• You have taken ML models from research/prototype to production at scale.
• You are comfortable designing and running A/B experiments, and you know how to choose the right offline and online metrics.
• You combine product intuition with technical depth. You care about making the patient experience meaningfully better, not just optimizing a model score.

Nice to have

• Experience with matching systems or 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.

Our interview process

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 & Benefits:

The expected base pay range for this position is $257,600 - $322,000, 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