Director, Engineering - Patient

1 in 4 people in the US have a treatable mental health condition, but most providers don't accept insurance, making therapy too expensive for most people. Headway’s mission is to fix this by building a new mental healthcare system everyone can access. We started by solving the biggest barrier to care: insurance. The admin work - credentialing, claims, payment reconciliation - is a nightmare. We’ve automated that. But we’re going further. Over 70,000 providers across all 50 states run their practice on our software, serving over 1 million patients. We are building the best tools for therapists to run their entire practice, reimagining the experience of finding a therapist, and investing in the platform foundations to enable this at scale. We aren’t just a billing layer; we are becoming the platform where care actually happens. We’re a Series D company with $325M+ in funding (a16z, Accel, GV, etc.), looking for exceptional people to help us achieve this mission. 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 Headway Headway’s mission is to build a new mental health care system that everyone can access. We’ve built technology that takes the hardest parts of mental healthcare — finding the right provider, navigating insurance, managing payments — and makes them simple. We’re now one of the fastest-growing companies in healthcare, with more than 200,000 patients finding care through Headway and thousands of therapists using our platform to grow their practices. About Patient Core Experience at Headway The Patient Core Experience team owns how patients find the right therapist on Headway. From search through the first several sessions, our four engineering pods — Onboarding, Profiles + Checkout, Ranking + Relevance, and Activation — build the systems that make great therapeutic matches happen. We operate a three-sided marketplace (patients, providers, payers) with real complexity and massive impact. We’re evolving from a provider directory into an intelligent matching platform that uses communication style, data‑backed expertise signals, and patient‑reported outcomes to connect people with therapists who are genuinely right for them. Principles that guide us: Matching quality is the foundation of therapeutic outcomes — we obsess over getting patients to the right provider We ship fast and learn fast, but we protect patient trust above all else We build for the whole marketplace: patients, providers, and payers ML powers our systems, but empathy drives our product The Problems You’ll Solve This role exists because we have hard, specific challenges that need senior engineering leadership to crack. Here’s what your first year looks like: Build an ML‑powered matching system from the ground up. Our current matching is largely filter‑based. We need to move to ML‑powered ranking that incorporates provider communication style, expertise signals, and patient outcome data — without degrading the patient experience during the transition. You’ll define the technical strategy for how we get there and own the execution across multiple pods. Rearchitect team topology as the product evolves. We have four pods today, but the boundaries between ranking, activation, and onboarding will shift as we move toward intelligent matching. You’ll need to evolve team structure, ownership boundaries, and technical interfaces as the product changes shape. This includes scaling the org from ~18 to ~25+ engineers while maintaining velocity and quality. Close the gap between engineering output and patient outcomes. We have patient funnel metrics (intake‑to‑match, match‑to‑book, book‑to‑retained) but engineering doesn’t yet co‑own them tightly enough with Product and Data. You’ll establish the operating model where engineering, product, and data science jointly own these metrics in a true triad — not one where engineering is an execution arm. Define how your teams build software in the AI era. This isn’t about adding a bullet point on AI tooling. You’ll set concrete standards for how your ~30 engineers use AI‑assisted development — how it changes code review, testing strategy, onboarding, and potentially team composition. You’ll also own the AI/ML strategy for the product itself: where we use ML models vs. heuristics, how we handle explainability in a healthcare context, and how we build patient trust in AI‑driven recommendations. Key Responsibilities Set engineering strategy for the core patient experience in partnership with Product and Data Science leadership Lead 3 Engineering Managers; scale the org from ~18 to ~30+ engineers over the next 18 months Co‑own patient funnel metrics with your Product and Data counterparts — not just deliver against them Drive delivery of ML‑powered ranking, reimagined patient onboarding, and patient activation systems Build an engineering culture with clear standards for velocity, quality, and technical excellence — starting with honest assessment of where we fall short today What You Bring Required experience: 10+ years of software engineering experience, 5+ years managing engineering managers Led engineering for a consumer or marketplace product where search, matching, ranking, or personalization was core to the business Scaled an engineering org through a high‑growth phase (25+ to 50+) while maintaining velocity and quality Technically strong enough to make sound architecture calls on ranking/ML systems, marketplace infrastructure, and consumer‑facing surfaces — you don’t write code daily, but you can review a system design and spot the problems Experience shipping ML‑powered product features (search ranking, recommendations, personalization) at consumer scale Track record of moving business metrics (conversion, retention, engagement) through engineering‑product partnership, not just delivering features on time Comfort working in a regulated industry where you can’t just ship fast — you need to reason about bias, explainability, and patient safety in ML systems Practiced perspective on AI‑augmented engineering workflows — you’ve led teams through adoption of AI development tools and have opinions on what changes and what doesn’t Nice‑to‑have: Healthcare experience or other regulated industries where data sensitivity and clinical consequences raise the stakes Experience with marketplace dynamics (supply/demand balancing, multi‑sided incentive design) Experience building LLM‑based product features (conversational interfaces, intelligent triage, AI‑assisted workflows) Experience rethinking team structure or hiring profiles in response to AI productivity gains Our Stack Our platform runs on Python (Django/FastAPI) and TypeScript/React on the frontend. Elasticsearch powers search and ranking. PostgreSQL and Redis handle data storage and caching. We use dbt and Snowflake for data pipelines, Temporal for workflow orchestration, and custom ML models for matching. Everything runs on AWS. You won’t be writing code daily, but you’ll need to engage deeply enough with these systems to make sound technical and organizational decisions. You’ll Love This Role If You Want To Solve a genuinely hard problem at the intersection of ML, marketplace dynamics, and healthcare — where getting matching right has real clinical consequences Shape an engineering org during a foundational transition, with high autonomy and strong executive support Co‑own patient outcomes, not just engineering output Work at a company where the mission isn’t marketing copy — patients are actually getting access to therapy they couldn’t get before Compensation and Benefits: The expected base pay range for this position is $264,000 to $330,000, 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 We believe a team’s strength is in its people, and we cannot achieve this mission without a team that reflects the diversity of this problem – across race, ethnicity, gender, sexuality, age, national origin, religion, family status, disability, military status, and experience. Headway is committed to the full inclusion of all qualified individuals. As part of this commitment, Headway will ensure that persons with disabilities are provided with reasonable accommodations. If reasonable accommodation is needed to participate in the job application or interview process, to perform essential job functions, and/or receive other benefits and privileges of employment, please inform the recruiter when they contact you to schedule your interview. Headway participates in E‑Verify. To learn more, click here. #J-18808-Ljbffr co-elevate