Staff Engineer - AI Comms Platform at Series D Healthtech

Headway.co; United States; Remote; USD 220,000 - 290,000; Full time

Benefits offered by this job

Medical, dental, vision

HSA/FSA

401(k) with match

Parental leave

Job summary

Headway in the United States is seeking a Staff Engineer to anchor the Journey team that builds the agentic communications engine for patients and providers. You will own the architecture of the multi-vendor delivery stack, design the decision engine, and drive LLM-powered personalization from concept to production, partnering with marketing, product, and engineering.

This is a fully remote role with broad impact on patient acquisition and health outcomes.

Qualifications

• 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.

Responsibilities

• Own the architecture of how Headway communicates at scale across a multi-vendor stack.
• Design and evolve the decision engine, experimentation layer, and channel orchestration.
• Set the technical direction for a unified messaging ledger and AI-powered personalization from concept to production.
• Collaborate cross-functionally with marketing, product, CX, and the patient org to impact acquisition, retention, and outcomes.

Skills

High-volume systems

Staff-level leadership

LLM personalization

Cross-functional influence

Reliability engineering

Tools

Python 3

TypeScript

FastAPI

React

Postgres

Redis

Kafka

Spark

AWS

Job description

Staff Engineer - AI Comms Platform at Series D Healthtech - Remote

This Staff Engineer role at Headway sits at a genuinely interesting technical intersection: high-volume communications infrastructure + AI/LLM personalization + healthcare impact. For engineers looking to level up into or solidify Staff-level scope, this is a strong opportunity.

Compensation context: No salary is listed, but Staff Engineer roles at Series D health-tech companies in the US typically range from $220,000-290,000 total comp (base + equity), varying by location and equity stage. At $325M+ raised, Headway's equity may carry meaningful upside but is in later dilution stages.

Skills you'll build:

• Agentic AI and LLM systems in production - one of the most in-demand skill sets of 2024-2026


• Event-driven architecture at scale (Kafka, Spark) - transferable across industries


• Multi-vendor platform orchestration and build-vs-buy decision-making at Staff level


• Experimentation infrastructure (A/B testing, personalization) - highly valued in growth and product-led companies

Culture signals: \"Small but mighty\" team, Series D stage (post-product-market fit but still scaling fast), mission-driven framing. This suggests autonomy with accountability - green flag for senior ICs who want ownership. The explicit mention of psychological safety (\"Optimize for trust\") is a positive cultural signal.

Green flags: Clear technical scope, cross-functional influence, AI-forward roadmap. Watch for: No explicit remote policy or salary transparency - clarify both early in the process.

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.

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 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 iterating.


• 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


• Infrastructure: AWS (Fargate, ECS, S3, and more), Spark and Kafka


• Version Control: GitHub, PagerDuty


• Vulnerability Management: Snyk, Semgrep


• 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. Additional experiences that 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

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 .

Is this Staff Engineer role fully remote? The job posting does not explicitly state remote or in-office status, but Headway is a US-based company that participates in E-Verify, implying US work authorization is required. Candidates should confirm the remote policy directly with the recruiter. What technical stack does the Journey team use? The team works with Python 3, TypeScript, FastAPI, React, Postgres, Redis, Kafka, Spark, and AWS infrastructure. For communications delivery, they use Knock, Iterable, Twilio, and Mailgun. What level of experience is required for this role? Headway is seeking candidates with 8+ years of software engineering experience, including meaningful time at Staff-level or equivalent, with hands‑on experience building high-volume event-driven communications platforms. Does Headway offer a 401(k) match? Yes, Headway offers a 401(k) with a match, noted as starting in 2027, along with medical, dental, vision, HSA/FSA, Carrot Fertility reimbursement, and paid parental and caregiver leave. What is the main focus of the Journey team at Headway? The Journey team builds and owns Headway's communications engine - deciding which message, channel, and timing reaches each patient and provider. They are currently developing an agentic, AI-driven system that improves with every interaction.

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