You will report into Headway's Data organization, a mission-critical pillar that ensures our data assets are accurate, timely, and accessible. Trustworthy data infrastructure is foundational to Headway's growth — enabling every team to build, measure, and improve with confidence.
You will partner closely with Data Science, Analytics, Product, and Engineering to deeply understand and anticipate the data needs of a fast-growing healthcare company. You will define the right architectural investments, proactively surface reliability and scalability risks, and use engineering rigor to guide decisions from early design through launch and iteration.
You will
Lead and grow a high-performing team of Data Engineers, fostering a culture of technical excellence, ownership, and craftsmanship.
Develop quarterly roadmaps with cross-functional partners on Data Science, Operations and Engineering, align Data Engineering resources, and oversee execution of timely, high-quality work.
Own the architecture and reliability of Headway's data platform — including our data warehouse, ingestion pipelines, transformation layer (dbt), and orchestration systems.
Identify and prioritize platform projects that enable better self-service and standardization across teams and pods, reducing bottlenecks and empowering stakeholders to get the data they need on their own.
Define and champion engineering standards: data modeling conventions, pipeline observability, SLA frameworks, and data quality monitoring.
Partner cross-functionally to design and build the data infrastructure that powers analytics, experimentation, ML models, and operational tooling at scale.
Lead the team in finding practical ways to leverage AI in data engineering workflows, with a clear view of what’s feasible today and what isn’t yet.
Stay close to the work by engaging directly with strategic technical challenges, surfacing gaps in our platform capabilities before they become bottlenecks.
Translate complex data decisions into clear, actionable recommendations for executive stakeholders.
You will love this role if
You have 8+ years of experience in data engineering or related roles
You have 3+ years of experience managing and developing teams
You have experience building and scaling data platforms in a high-growth, cloud-native environment (highly preferred)
You have proven success partnering cross-functionally with Data Science, Analytics, and Product Engineering
You have deep expertise in data warehouse design, pipeline architecture, and transformation frameworks — with the ability to coach others through complex technical trade-offs
You’re forward-thinking about AI, with hands-on experience using it to improve team workflows and a pragmatic sense of where it adds real value
COMPREHENSIVE BENEFITS
Medical, dental, vision, HSA/FSA, 401(k) including match for 2027!, Carrot Fertility reimbursement, and paid parental, medical and caregiver leave.
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.
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