[All remote jobs](https://jobicy.com/jobs.md)[![Headway.co logo](https://jobicy.com/data/server-nyc0409/galaxy/mercury/2021/12/068391a61855fb604bca051cafe3c510.jpeg)](https://jobicy.com/company/headway.md)[Headway.co](https://jobicy.com/company/headway.md) # Staff Software Engineer (Journeys) AI Summary Headway is seeking a Staff Software Engineer to serve as the technical anchor for its Journey team and its patient/provider communications platform. The role owns architecture for a high-volume, event-driven, multi-vendor delivery stack spanning email, SMS, decisioning, experimentation, and a unified message ledger. The engineer will bring LLM-powered personalization into reliable production systems while shaping technical direction across engineering, marketing, CX, product, and patient teams. Success requires deep experience with scalable distributed systems, communications platforms, experimentation infrastructure, and influencing without direct authority. The work directly supports patient acquisition, retention, and access to mental healthcare.[Apply for this job](#job-application)[View company](https://jobicy.com/company/headway.md)ShareRemote from[USA](https://jobicy.com/job-region/usa.md)SalaryUSD 265k–331k / yrDepartment[Software Engineering](https://jobicy.com/categories/engineering.md)EmploymentFull TimeExperienceSeniorPublished7 Nov 2026Apply before7 Dec 2026Listing views43Application actions2Application toolkit ## Make your next move. Prepare your resume, explore your fit, and draft a cover letter for this opportunity. Opportunity details ## About this role. 1 in 4 people in the US have a treatable mental health condition, but most providers don’t accept insurance, making therapy too expensive for most people. Headway’s mission is to fix this by building a new mental healthcare system everyone can access. We started by solving the biggest barrier to care: insurance. The admin work – credentialing, claims, payment reconciliation – is a nightmare. We’ve automated that. But we’re going further. Over 90,000 providers across all 50 states run their practice on our software, serving over 2.6 million patients. We are building the best tools for therapists to run their entire practice, reimagining the experience of finding a therapist, and investing in the platform foundations to enable this at scale, and building much of it with AI. We aren’t just a billing layer; we are becoming the platform where care actually happens. We’re a Series D company with $325M+ in funding (a16z, Accel, Spark Capital, etc.), looking for exceptional people to help us achieve this mission. We want your time here to be the most meaningful experience of your career. Join us, and help change mental healthcare for the better. About engineering at Headway: * Building a new mental healthcare system at Headway is only possible because of the scale and leverage that software can provide. The engineering team at Headway is a small but mighty team using technology to build that future (and have a fun time while doing it!). ### Principles that guide us: * Focus on the mission: We view software as a means of effecting change in the world, not as an end unto itself. We write software to empower our patients and therapists to better solve the problems they’re facing. * Ship small, learn fast: We are building new and novel products and believe that we learn what our users need by quickly shipping and iteration * Everything is a product: Whether it’s our patient search experience or a developer productivity improvement, we treat everything we build at Headway as a product with end-users in mind. * Optimize for trust: We believe that engineers should be continually learning. To learn effectively and to be productive, engineers must feel safe asking questions and discussing mistakes. Tools we use: * Languages: Python 3, TypeScript * Libraries & Frameworks: FastAPI, SQLAlchemy, React, Remix, Next.js * Datastores: Postgres, Redis * Infrastructure: AWS (Fargate, ECS, S3, and more), Spark and Kafka * Monitoring: Datadog, PagerDuty, Sentry * Version Control: Github, PagerDuty * Vulnerability Management: Snyk, Semgrep * Cloud Security: Lacework * Delivery: Knock (transactional + product notifications), Iterable (lifecycle marketing + campaigns), Twilio, Mailgun About the Journey Team at Headway * The Journey team powers how Headway reaches every patient and provider at the right moment, on the right channel – email, SMS and other communication channels. We’re building the next chapter: an agentic communications engine that learns which message, which channel, and which timing works best for each person — and gets smarter with every send. We own the full stack: from the delivery layer (Knock for transactional, Iterable for lifecycle), to the decision engine we’re building today. 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 ### Comprehensive benefits: Medical, dental, vision, HSA/FSA, 401(k) including match for 2027!, Carrot Fertility reimbursement, and paid parental, medical and caregiver leave. 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. Headway participates in E-Verify. To learn more, click [here.](https://www.e-verify.gov/sites/default/files/everify/posters/EVerifyParticipationPoster.pdf) A notice to Headway applicants: To protect yourself against phishing and recruitment fraud, please note that Headway only accepts applications through our official careers page at [https://headway.co/careers](https://jobicy.com/company/headway.md). Headway will never refer you to external websites, ask for payment or personal information, or conduct interviews via messaging apps. All official communication will come from a @[findheadway.com](http://findheadway.com) email address. If you are contacted by someone claiming to be from Headway via an unofficial channel, please do not share any information and report it as spam. Show more [Apply now >](https://jobicy.com/jobs/159647-staff-software-engineer-journeys.md) * ![Upload CV](data:image/svg+xml;base64,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) ### Upload your resume now To unlock remote work opportunities and be discovered by global employers. This job listing has been manually reviewed by the Jobicy Trust & Safety Team for compliance with our posting guidelines, including verification of the company's legitimacy, accuracy of job details, clarity of remote work policy, and absence of misleading or fraudulent content. ## Role DNA A quick view of the complexity, pace, ownership and collaboration implied by the job description. ### Job Complexity 5/5EasyHard ### Pace & Pressure 5/5RelaxedFast-paced ### Autonomy Level 5/5GuidedFull ownership ### Communication Load 5/5IndependentCollaborative AI insightThis is a staff-level architecture role involving millions of communication events, multiple external vendors, experimentation, and production AI reliability. It requires independent technical leadership and alignment across several non-engineering and engineering stakeholders. ## Salary analysis Estimated compensation compared with the broader US market for similar roles. Estimated job median (per year)Highly competitive$298,000US market range (per year)$230k–$350k0$385.00k AI insightThe employer discloses a yearly base-pay range of $265,000–$331,000 USD, with a midpoint of $298,000. The estimated US market range for a staff software engineer leading high-scale communications and AI platform architecture is $230,000–$350,000 USD per year; this is an AI estimate, not verified salary research. ## Core skills Skills and capabilities most closely associated with this opportunity. [Python](https://jobicy.com/jobs?search_keywords=Python.md)[TypeScript](https://jobicy.com/jobs?search_keywords=TypeScript.md)[Event-driven architecture](https://jobicy.com/jobs?search_keywords=Event-driven%20architecture.md)[Distributed systems](https://jobicy.com/jobs?search_keywords=Distributed%20systems.md)[High-throughput messaging](https://jobicy.com/jobs?search_keywords=High-throughput%20messaging.md)[Email delivery platforms](https://jobicy.com/jobs?search_keywords=Email%20delivery%20platforms.md)[SMS delivery platforms](https://jobicy.com/jobs?search_keywords=SMS%20delivery%20platforms.md)[AWS](https://jobicy.com/jobs?search_keywords=AWS.md)[Kafka](https://jobicy.com/jobs?search_keywords=Kafka.md)[PostgreSQL](https://jobicy.com/jobs?search_keywords=PostgreSQL.md)[Redis](https://jobicy.com/jobs?search_keywords=Redis.md)[A/B testing](https://jobicy.com/jobs?search_keywords=AB%20testing.md)[LLM production systems](https://jobicy.com/jobs?search_keywords=LLM%20production%20systems.md)[System architecture](https://jobicy.com/jobs?search_keywords=System%20architecture.md)[Cross-functional leadership](https://jobicy.com/jobs?search_keywords=Cross-functional%20leadership.md) Sample interview questionsHow would you design a unified message ledger for email, SMS, and future communication channels?I would define an immutable event model with a canonical message identity, recipient and consent metadata, channel-specific delivery states, provider identifiers, idempotency keys, and correlation IDs. Events would be published through a durable stream, with projections for operational queries and analytics. The design would include retention controls, auditability, and privacy safeguards appropriate for healthcare-related workflows. How do you evaluate build-versus-buy decisions for a communications platform? I assess strategic differentiation, reliability requirements, delivery volume, compliance needs, integration complexity, total cost of ownership, and vendor lock-in. I generally use vendors for commodity delivery capabilities while owning the orchestration, decisioning, data model, and experimentation layers that create durable product advantage. What controls would you implement for LLM-powered communication personalization in production? I would use constrained generation, approved templates, structured outputs, policy checks, evaluation datasets, monitoring for quality and latency, and safe fallbacks to deterministic content. I would also separate experimentation from broad rollout, log decision context for review, and ensure sensitive data handling is minimized and governed. How would you improve reliability for a system sending millions of events per month? I would establish explicit SLOs for acceptance, delivery, latency, and correctness; implement idempotent consumers, retries with backoff, dead-letter handling, rate limiting, and vendor failover where appropriate. End-to-end observability, replayable event streams, capacity testing, and incident runbooks would help the team detect and recover from failures quickly. How do you influence technical direction when you do not manage the teams involved? I start by understanding each team’s goals and constraints, then make trade-offs visible through concise architecture proposals, prototypes, and measurable outcomes. 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