8+ years of software engineering experience, primarily at Staff-level or equivalent
Proven expertise in designing and building high-volume, event-driven communications platforms
Fluent in multi-vendor delivery stacks with strong build-vs-buy insights
Hands-on experience with experimentation infrastructure, including A/B testing and personalization
Familiarity with production-level LLM-powered systems, focusing on reliability and performance
Proven track record of influencing technical direction across teams.
Responsibilities
Serve as the technical anchor for the Journey team, overseeing architecture of communication systems
Design and enhance the decision engine, experimentation layer, and channel orchestration
Set the technical direction for a multi-vendor communications stack
Own the unified message ledger, ensuring accuracy and reliability
Drive AI-powered personalization initiatives from concept to deployment
Collaborate closely with marketing, CX, product, and patient teams to influence key health outcomes
Benefits
Cross-functional teamwork influencing patient acquisition and retention
Opportunities to work at the intersection of AI and communications
High-leverage role with a focus on impactful technical architecture
Potential to shape the future of healthcare communication systems
Supportive environment for engineers to grow and improve technical capabilities.
Full Job Description
About this role
We're looking for a Staff Engineer to be the technical anchor of the Journey team. This is a senior IC role - the person who owns the architecture of how Headway communicates at scale. You'll design and evolve the decision engine, experimentation layer, and channel orchestration that will define how Headway reaches patients and providers for years to come. You'll set the technical direction for a multi-vendor communications stack, own the unified message ledger, and bring LLM-powered personalization from concept to production.
This role is high-leverage and cross-functional. You'll work closely with marketing, CX, product, and the patient org - and your work will directly impact patient acquisition, retention, and health outcomes.
Who you are:
We're looking for experienced engineers who have the ability to deal with ambiguity and learn new technologies and systems. Below are some additional experiences we think help engineers succeed at Headway.
A systems thinker who holds the architecture of a complex, multi-vendor platform and guides the team through it
An engineer who has shipped high-throughput, event-driven systems in production and knows what reliability requires
A communicator who translates technical trade-offs for non-technical stakeholders and drives alignment across marketing, product, and engineering
Genuinely excited about the intersection of AI and communications - and thoughtful about what makes AI-in-the-loop systems reliable at scale
A leader who earns influence through technical depth and leaves teams more capable than they found them
Experience we're seeking
8+ years of software engineering experience, with meaningful time at Staff-level or equivalent
Designed and built high-volume, event-driven communications platforms - email, SMS, push, or equivalent - at millions of events per month
Fluency with multi-vendor delivery stacks; strong opinions about build-vs-buy trade-offs at the platform layer
Experience building or working closely with experimentation infrastructure - A/B testing, engagement analytics, personalization, or recommendation systems
Exposure to LLM-powered systems in production - not just API consumption, but thinking about reliability, latency, and quality at scale
Demonstrated ability to shape technical direction across teams without direct authority
