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Staff Software Engineer

Location: Remote
Compensation: To Be Discussed
Reviewed: Wed, Aug 12, 2026
This job expires in: 28 days

Job Summary

Seeking a full-time Staff Software Engineer to serve as the technical anchor for the Journey team, responsible for designing and evolving a multi-vendor communications stack, including a decision engine and channel orchestration, while working remotely.

Key responsibilities
  • Design and evolve the architecture for Headway's communication systems at scale
  • Lead the development of the decision engine and experimentation layer to optimize patient and provider outreach
  • Collaborate cross-functionally with marketing, product, and engineering teams to enhance patient acquisition and retention
Required qualifications
  • 8+ years of software engineering experience, including time at a Staff-level or equivalent
  • Experience designing and building high-volume, event-driven communication platforms
  • Fluency with multi-vendor delivery stacks and strong opinions on build-vs-buy trade-offs
  • Familiarity with experimentation infrastructure, including A/B testing and personalization systems
  • Exposure to LLM-powered systems in production, focusing on reliability and performance at scale

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