Director of Engineering - Data Platform

Headway•Seattle, WA

3h•$249,600 - $312,000

About The Position

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. Headway is building a new mental healthcare system that everyone can access. Data is critical to that mission: it powers how we operate at scale, how we make decisions, and how we build trust in everything from financial systems to product experiences. We are hiring a Director of Engineering, Data Platform to own the strategy, execution, and reliability of Headway’s data platform. This is a senior leadership role, reporting directly to the Head of Data, responsible for the systems and standards that enable high-quality analytics, data science, and data-powered product development across the company all while taking an AI-forward stance. We now need a leader who can set direction for the next 2+ years of scale, build a durable platform roadmap, and run a high-performing organization that delivers.

Requirements

Experience leading platform or data engineering teams, including managing managers and scaling orgs.
Strong track record hiring, developing talent, and driving alignment across senior stakeholders.
Deep experience with modern data platforms and data product patterns (modeling, governance, semantic layers, reliability).
Proven ability to simplify and modernize messy systems while improving quality and speed.
Practical point of view on how AI is changing data work and what it requires to be trustworthy: governance, lineage, access control, and reliable metric definitions.
Ability to evaluate new tools with a bias toward measurable outcomes, security, and operational excellence.
Track record owning reliability for critical systems, including monitoring, incidents, and continuous improvement.
Ability to run against clear platform health metrics (freshness, correctness, availability, cost, cycle time).
Strong communicator who creates clarity, drives decisions, and builds durable partnerships.

Nice To Haves

Experience supporting ML/AI workflows (feature/data governance, retrieval over trusted data, or analytical copilots/agents).
Healthcare, fintech, or other high-trust domains.

Responsibilities

Set the platform vision and roadmap (AI-ready by default)
Own the multi-year strategy for Headway’s data platform, balancing near-term delivery with durable foundations.
Build an AI-ready data layer that makes it fast and safe to go from question to trusted answer: governed access, lineage, quality, and consistent metric definitions.
Modernize and simplify the stack: reduce redundancy, improve reliability, and lower cost.
Run a high-trust, high-availability platform
Ensure critical datasets are accurate, discoverable, well-modeled, and operationally excellent.
Establish engineering standards: testing, observability, SLAs, incident response, access controls, and data quality monitoring.
Define “certified” data products with clear ownership so teams can self-serve with confidence.
Lead and scale the Data Platform org
Lead managers and senior ICs; hire and develop a high-performing team.
Build scalable operating mechanisms: planning, roadmaps, execution reviews, and healthy cross-functional rituals.
Use AI to compress the information to insight loop, safely
Enable AI-assisted analytics by investing in the platform primitives it depends on: metadata, catalog, lineage, governed context, and a semantic layer.
Put guardrails in place so AI outputs are grounded in trusted sources, auditable when needed, and secure by design.
Be the platform partner for Product and the business
Partner with Engineering, Product, Analytics, and Data Science leaders to align priorities and deliver outcomes.
Turn ambiguous needs into clear plans, sequencing, and trade-offs.

Benefits

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