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.

What you’ll do:

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.

What we’re looking for:

Leadership

• 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.

Technical depth

• 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.

AI-forward, rigor-first

• 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.

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).

Cross-functional influence

• 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.

Compensation and Benefits:

The expected base pay range for this position is $264,000 - $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

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