Senior Engineering Manager, Headway

• 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

Desirable

• 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
• 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
• 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

• 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!