Staff Software Engineer (Journeys)

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

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

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

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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