Staff Data Infrastructure Engineer

Join Headway, a company redefining access to mental healthcare. As a Staff Data Infrastructure Engineer, you will architect, lead, and evolve the foundational systems that power our entire data organization. You will serve as a technical anchor across multiple teams, make consequential architectural decisions, and help shape Headway's engineering culture. This role requires deep infrastructure expertise, organizational instincts, and a track record of driving technical strategy and cross-functional alignment.

• Architect, lead, and evolve the foundational systems that power the entire data organization, including new AI-driven workflows.
• Set technical direction for data infrastructure at the company, making data engineers, analysts, and ML practitioners more effective through the systems and standards put in place.
• Drive technical strategy and cross-functional alignment, including defining roadmaps for a data platform or infrastructure domain.
• A technical leader who combines deep infrastructure expertise with the organizational instincts to drive alignment across teams. You thrive in ambiguity, operate with a high degree of ownership, and are as comfortable setting technical direction as you are building. You make other engineers better through code, architecture review, documentation, and mentorship
• Experience leading technical initiatives end-to-end across multiple teams and codifying engineering standards
• Experience maintaining and scaling pipeline orchestration infrastructure (Airflow/Astronomer preferred)
• 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
• 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)
• Track record of driving technical strategy and cross-functional alignment, including defining roadmaps for a data platform or infrastructure domain
• 10+ years as a Data Platform Engineer, Software/Infrastructure Engineer specializing in data, or Data Engineer in a high-code, high-scale environment
• 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
• Mentorship track record growing junior and mid-level engineers
• 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 PHI
• Greenfield platform development in a high-growth startup
• Docker, GitHub Actions, dbt, Spark
• Build vs. buy decision-making and vendor evaluation