Staff Data Infrastructure Engineer at headway – New York | Jobyssey

1 in 4 people in the US have a treatable mental health condition, but most providers don't accept insurance, making therapy too expensive for most people. Headway’s mission is to fix this by building a new mental healthcare system everyone can access. We started by solving the biggest barrier to care: insurance. The admin work - credentialing, claims, payment reconciliation - is a nightmare. We've automated that.

But we're going further. Over 75,000 providers across all 50 states run their practice on our software, serving over 1 million patients. We are building the best tools for therapists to run their entire practice, reimagining the experience of finding a therapist, and investing in the platform foundations to enable this at scale. We aren't just a billing layer; we are becoming the platform where care actually happens.

We're a Series D company with $325M+ in funding (a16z, Accel, Spark Capital, etc.), looking for exceptional people to help us achieve this mission. We want your time here to be the most meaningful experience of your career. Join us, and help change mental healthcare for the better.

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

We believe a team's strength is in its people, and we cannot achieve this mission without a team that reflects the diversity of this problem – across race, ethnicity, gender, sexuality, age, national origin, religion, family status, disability, military status, and experience. Headway is committed to the full inclusion of all qualified individuals. As part of this commitment, Headway will ensure that persons with disabilities are provided with reasonable accommodations. If reasonable accommodation is needed to participate in the job application or interview process, to perform essential job functions, and/or receive other benefits and privileges of employment, please inform the recruiter when they contact you to schedule your interview.

Headway participates in E-Verify. To learn more, click here.

A notice to Headway applicants: To protect yourself against phishing and recruitment fraud, please note that Headway only accepts applications through our official careers page at . Headway will never refer you to external websites, ask for payment or personal information, or conduct interviews via messaging apps. All official communication will come from a @ email address. If you are contacted by someone claiming to be from Headway via an unofficial channel, please do not share any information and report it as spam.

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