About Data Platform at Headway

Building a new mental healthcare system at Headway is only possible because of the scale and leverage that software and data can provide. The Data Platform team is a group of Data Engineers and Data Infrastructure Engineers who build and own our Snowflake data warehouse, data ingestion tooling, AWS infrastructure, CI/CD, and data developer experience. As we scale, we're looking for a Staff Data Infrastructure Engineer to architect, lead, and evolve the foundational systems that power our entire data organization, including new AI-driven workflows being adopted by non-technical staff. You'll serve as a technical anchor across our Data Analytics & Engineering, Product Engineering, and Machine Learning teams. This is not an analytics role.

Who you are

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 we're seeking:

• 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

Bonus points for:

• 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

You'll love this role if you want to:

• Set technical direction for data infrastructure at a company redefining access to mental healthcare
• Serve as a force multiplier, making data engineers, analysts, and ML practitioners more effective through the systems and standards you put in place
• Own consequential architectural decisions from whiteboard to production
• Build in a fast-paced environment where we ship multiple times per day and measure impact quickly
• Help shape Headway's engineering culture, processes, and documentation with the same rigor we bring to our products

Compensation and Benefits:

The expected base pay range for this position is $212,000 - $265,000, 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