Staff Software Engineer (Journeys)
Headway · Remote · Remote · San Francisco, CA · Seattle, WA · New York City ·
COMPENSATION
$265k – $331k
Listed on the employer's job board (Ashby)
- Staff level IC role
- Fully remote (US)
- Python + TypeScript
- Event-driven systems
- LLM integration
You will serve as the technical anchor for the Journey team, owning the architecture of Headway's communication platform at scale. Your work involves evolving the decision engine, experimentation layer, and channel orchestration to define how the company reaches users. You will bridge technical execution with strategic direction, bringing AI-powered personalization from concept to production while ensuring system reliability.
What you'll do
- Design and evolve the decision engine and channel orchestration architecture
- Own the unified message ledger and multi-vendor communications stack
- Bring LLM-powered personalization features from concept to production
- Guide the team through complex architectural decisions and trade-offs
- Collaborate with marketing, product, and CX to align technical solutions
- Ensure high reliability and throughput for millions of monthly events
What you'll need
- 8+ years of software engineering experience with Staff-level tenure
- Experience building high-volume, event-driven communication platforms
- Fluency with multi-vendor delivery stacks and build-vs-buy trade-offs
- Background in experimentation infrastructure or personalization systems
- Production experience with LLM-powered systems focusing on reliability
- Ability to shape technical direction across teams without direct authority
Stack
- Python 3
- TypeScript
- FastAPI
- React
- Next.js
- Postgres
- Redis
- AWS
- Kafka
- Datadog
How you'll work
- Fully remote position
- Based in the United States
- Series D funded company environment