Senior Engineering Manager (Ranking & Relevance)

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 systems that power this connection, from search and discovery to ranking and personalization. Our goal is to combine cutting-edge machine learning with robust product engineering to deliver a search experience that balances incentives for patients, providers, payers, and Headway’s growth.

The team sits at the heart of Headway’s marketplace, owning the technology that determines how patients discover and connect with therapists. This means working at the intersection of user experience, marketplace design, and applied machine learning.

About the role

We are looking for a Senior Engineering Manager to lead and grow our Ranking & Relevance engineering organization. This role is ideal for a leader who has built search, ranking, or recommendation systems and knows what good looks like in these domains. You will guide a cross-disciplinary team of software and machine learning engineers to design, build, and scale Headway’s matching and personalization systems.

You’ll partner closely with product, data, design, and operations leaders to create the foundation for how millions of patients connect with the right therapist. You’ll play a central role in shaping the team’s strategy, technical direction, and culture—helping Headway build the mental healthcare marketplace of the future.

What you’ll do

• Lead and grow a team of software and ML engineers building Headway’s search, ranking, and personalization systems.
• Define and drive the technical strategy for how patients discover and connect with providers, from search retrieval to model-driven ranking.
• Partner with cross-functional leaders to translate business objectives into measurable outcomes that improve matching relevance, patient conversion, and business growth.
• Build and scale reliable search infrastructure, leveraging technologies such as Elasticsearch and modern ML pipelines.
• Mentor and develop engineers and emerging leaders, fostering a culture of technical excellence, curiosity, and accountability.
• Collaborate with peers across Engineering, Product, and Data Science to define success metrics, design A/B experiments, and continually improve model and product performance.
• Contribute to broader engineering leadership efforts as Headway continues to scale its systems and teams.

Who you are

• You have 3–5+ years of engineering management experience leading high-performing software or ML engineering teams, ideally in ranking, search, or recommendation systems.
• You have 5+ years of prior experience as a software or ML engineer, building large-scale distributed systems or ML-powered products.
• You’ve built or scaled search or ranking systems from scratch, and understand what excellence looks like across retrieval, relevance, and personalization.
• You’re comfortable managing teams that span ML and software engineering, bridging disciplines to deliver cohesive, user-impacting systems.
• You’re a strong cross-functional partner who can balance competing marketplace incentives, aligning patient, provider, and business goals into a coherent technical vision.
• You bring product intuition to your technical leadership, caring deeply about the user experience and long-term system outcomes.
• You foster a culture of learning, psychological safety, and high performance, developing your team into thoughtful builders and decision-makers.

Nice to have

• Experience building and scaling systems using Elasticsearch or similar search technologies.
• Prior experience in health tech, marketplaces, or other highly regulated, multi-sided domains.
• Exposure to ML infrastructure such as model deployment, retraining pipelines, and monitoring tools.
• Familiarity with modern ranking and personalization approaches (e.g., embeddings, vector search, or reinforcement learning for recommendations).

Our interview process

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

• 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. 
• First rounds: You'll meet with an engineering leader on the team to go deeper into your team and people leadership experiences and complete one technical (systems design) interview.
• Final rounds: You’ll meet team members across product and engineering leadership for multiple behavioral interviews, leaving you with a fuller picture of what it’s like to work at Headway.
• 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 $234,600 - $276,000, based on a variety of factors including qualifications, experience, and geographic location. In addition to base salary, this role may be eligible for performance-based variable compensation and 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