Staff Software Engineer (Journeys)

Salary: $180,000 - 250,000 per year Requirements:

• Were seeking a senior software engineer with 8+ years of experience, including substantial time at Staff level or an equivalent scope.
• We want someone who has designed and delivered high-volume, event-driven communications systems such as email, SMS, push, or similar platforms handling millions of events per month.
• Were looking for strong experience with multi-vendor delivery architectures and thoughtful judgment around build-versus-buy decisions at the platform layer.
• We value experience with experimentation tooling, including A/B testing, engagement analytics, personalization, or recommendation systems.
• We prefer candidates with production exposure to LLM-powered systems who understand reliability, latency, and quality considerations at scale.
• We need a systems thinker who can own the architecture of a complex, multi-vendor platform and help guide the team through technical complexity.
• We want an engineer who communicates clearly with non-technical stakeholders and can align marketing, product, CX, and engineering.
• Were looking for someone who is excited about the intersection of AI and communications and who understands what makes AI-in-the-loop systems dependable in production.
• We value a leader who influences through technical depth and helps teams become stronger and more capable.
• We seek someone comfortable with ambiguity and able to learn new technologies and systems quickly.

• We want you to serve as the technical anchor for our Journey team and own the architecture behind how we communicate at scale.
• You will design and evolve our decision engine, experimentation layer, and channel orchestration that shape how we reach patients and providers.
• You will set the technical direction for our multi-vendor communications stack.
• You will own our unified message ledger and help bring LLM-powered personalization from concept into production.
• You will work across marketing, CX, product, and our patient organization to drive alignment on high-impact initiatives.
• You will influence patient acquisition, retention, and health outcomes through the systems you build.
• You will lead technical decision-making across teams and contribute to a reliable, scalable communications platform.
• You will help build an agentic communications engine that learns the best message, channel, and timing for each person.

• AI
• LLM
• Marketing
• Spark
• API
• AWS
• Cloud
• Datadog
• FastAPI
• GitHub
• Kafka
• PagerDuty
• Python
• React
• Redis
• Security
• Sentry
• TypeScript

More:

Were Headway, and our mission is to build a new mental healthcare system that everyone can access. We started by removing the biggest barrier to care: insurance administration, and weve automated credentialing, claims, and payment reconciliation. More than 75,000 providers across all 50 states use our software to serve over 1 million patients. Were now expanding beyond billing into the full platform where care happens, building better tools for therapists, rethinking how people find a therapist, and investing in the foundations that make this possible at scale. Were a Series D company with more than $325M in funding from investors including a16z, Accel, and Spark Capital. Our engineering team is small, ambitious, and mission-driven, and we value shipping quickly, learning fast, and building with trust. The Journey team focuses on reaching patients and providers at the right moment through email, SMS, and other channels, and were building the next generation of intelligent communications. Were committed to inclusion, reasonable accommodations for qualified individuals with disabilities, and a supportive hiring process for all applicants.

last updated 33 week of 2026