Staff Data Infrastructure Engineer

About the role

Headway is a company dedicated to improving access to mental healthcare. Our mission is to build a new mental healthcare system that is accessible to everyone. We are currently seeking a Staff Data Infrastructure Engineer to join our team.

Responsibilities

• Architect, lead, and evolve the foundational systems that power our entire data organization.
• Drive technical strategy and cross-functional alignment, including defining roadmaps for a data platform or infrastructure domain.
• Lead technical initiatives end-to-end across multiple teams and codify engineering standards.
• Maintain and scale pipeline orchestration infrastructure (Airflow/Astronomer preferred).
• Design and operate cloud infrastructure at scale (AWS preferred) using infrastructure-as-code (Terraform, Pulumi, AWS CDK).
• Ensure data security and compliance in regulated environments, especially PHIG.
• Build in a fast-paced environment where we ship multiple times per day and measure impact quickly.
• Shape Headway's engineering culture, processes, and documentation with the same rigor we bring to our products.

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).
• Mentorship track record growing junior and mid-level engineers.

Qualifications

• 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 PHIG
• Docker, GitHub Actions, dbt, Spark
• Build vs. buy decision-making and vendor evaluation

Skills

• Technical leadership
• Ownership and alignment across teams
• Code, architecture review, documentation, and mentorship
• Technical direction for data infrastructure
• Force multiplier for data engineers, analysts, and ML practitioners
• Building in a fast-paced environment
• Shaping Headway's engineering culture, processes, and documentation

Benefits

• Compensation range: $212,000 - $265,000
• 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