Staff Data Infrastructure Engineer

About Headway

Headway’s mission is to build a new mental healthcare system that everyone can access. We started by automating the administrative work involved in insurance, which is a major barrier to care. Our platform serves over 1 million patients across all 50 states, and we are expanding to become the central hub for mental healthcare.

Job Details

We are a Series D company with $325M+ in funding, seeking exceptional people to join our mission. We are looking for a Staff Data Infrastructure Engineer to architect, lead, and evolve the foundational systems that power our entire data organization.

What You’ll Be Doing

• Architect, lead, and evolve the foundational systems that power our entire data organization
• Own consequential architectural decisions from whiteboard to production
• Mentor junior and mid-level engineers

Requirements

• 10+ years as a Data Platform Engineer, Software/Infrastructure Engineer specializing in data, or Data Engineer in a high-code, high-scale environment
• Track record of driving technical strategy and cross-functional alignment, including defining roadmaps for a data platform or infrastructure domain
• Deep expertise building full-stack data platforms: data warehousing, ingestion pipelines, orchestration, monitoring and alerting, CI/CD, developer tooling, cloud infrastructure, and third-party integrations
• Architectural fluency in warehouse design patterns, performance tuning, cost management, and permissions strategies on MPP analytics databases (Snowflake strongly preferred; Databricks, BigQuery, or Redshift also relevant)
• Experience leading technical initiatives end-to-end across multiple teams and codifying engineering standards
• Proficiency designing and operating cloud infrastructure at scale (AWS preferred) using infrastructure-as-code (Terraform, Pulumi, AWS CDK)
• Strong Python engineering skills; solid SQL foundations; comfort with distributed systems
• Experience maintaining and scaling pipeline orchestration infrastructure (Airflow/Astronomer preferred)

Bonus Points

• Agentic Data Engineering (automating data infrastructure tasks, auditing permissions, optimized CI)
• APM and observability tooling (DataDog, New Relic) and data quality/observability frameworks
• ETL/ELT best practices at scale
• Data security and compliance in regulated environments, especially PHIGreenfield platform development in a high-growth startup
• Docker, GitHub Actions, dbt, Spark
• Build vs. buy decision-making and vendor evaluation