8+ years of software engineering experience, including time in a Staff-level or equivalent position
Proven experience designing and building high-volume, event-driven communication platforms
Strong understanding of multi-vendor delivery stacks and trade-offs between build vs. buy
Hands-on experience with experimentation infrastructure, including A/B testing and engagement analytics
Familiarity with LLM-powered systems, focusing on reliability and performance at scale
Ability to influence technical direction across teams without direct authority
Responsibilities
Lead the architecture of Headway's communication systems to ensure effective patient engagement
Design and evolve high-throughput, event-driven decision engines and experimentation layers
Set the technical direction for a multi-vendor communications stack
Own and maintain the unified messaging ledger across platforms
Collaborate cross-functionally with marketing, product, and CX teams to drive alignment on technology initiatives
Benefits
High-leverage role that impacts patient acquisition, retention, and health outcomes
Opportunity to work at the intersection of AI and communications
Engagement with cross-functional teams directly influencing core architecture
Chance to shape technical direction in a collaborative environment
Exposure to a dynamic and evolving technological landscape
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
