---
title: 'Staff Software Engineer (Journeys) at Headway'
canonical: 'https://feeny.ai/job/staff-software-engineer-journeys-headway-remote-ng6e2khsh6xy'
type: 'job'
last_seen: '2026-09-20'
---

# Staff Software Engineer (Journeys) at Headway

- **Company:** [Headway](https://feeny.ai/companies/headway)
- **Location:** Remote
- **Employment:** full-time
- **Work type:** remote
- **Posted:** 2026-08-10
- **Last confirmed live:** 2026-09-20
- **Apply:** https://jobs.ashbyhq.com/headway/d123a2aa-7c3c-4833-bfc2-4d3356db1041

## Job description

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 75,000 providers across all 50 states run their practice on our software, serving over 1 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. 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

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. 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.

## About Headway

## Company Overview
- **One-liner**: Headway is building a new mental healthcare system by creating the first software-enabled national network of therapists who accept insurance, making care affordable and accessible.
- **Entity Type**: Private (Series D)
- **Headquarters**: New York City, New York, USA
- **Founded**: 2019
- **Founders**: Not publicly listed on primary sources

## Core Business
- **Primary industry**: Mental Healthcare Technology / HealthTech
- **Target customers**: B2B (therapists and group practices) and B2C (patients seeking mental health care)
- **Mission or purpose statement**: "To build a new mental healthcare system, rewired for access and affordability." [headway.co](https://headway.co/about-us)

## Products & Services
- **Headway Platform (Provider Side)**: A software platform that enables therapists and psychiatrists to accept insurance, manage billing, and grow their private practice. It removes the administrative burden of insurance credentialing and claims, allowing providers to focus on care.
- **Headway Platform (Patient Side)**: A marketplace where patients can find and book in-network therapists and psychiatrists, with costs as low as $0/session after insurance. The platform handles scheduling, insurance verification, and billing.

## Market Standing
- **Valuation/Market Cap**: Not publicly disclosed (Series D private company)
- **Key Metric**: Over $325 million in total funding raised (Series D) [builtin.com](https://builtin.com/company/headway)
- **Notable Investors/Partners**: Andreessen Horowitz (a16z), Accel, GV (Google Ventures), Spark Capital, Thrive Capital, Forerunner Ventures, and Health Care Service Corporation. [builtin.com](https://builtin.com/company/headway)
- **Growth Signals**: 
  - Network of over 70,000 therapists and psychiatrists across all 50 states [headway.co](https://headway.co/)
  - Over 30 million sessions held [headway.co](https://headway.co/)
  - Served over 1 million patients [builtin.com](https://builtin.com/company/headway)
  - 604 U.S.-based employees (Medium-sized company) [greatplacetowork.com](https://www.greatplacetowork.com/certified-company/7083261)
  - 259 Product + Tech employees [builtin.com](https://builtin.com/company/headway)
  - Named #48 on Fortune Best Workplaces in Health Care™ 2025 (Small And Medium) [greatplacetowork.com](https://www.greatplacetowork.com/certified-company/7083261)

## Competitive Advantages
- **Asset-free network model**: Unlike competitors that build their own clinics, Headway enables existing independent therapists to accept insurance without administrative burden, creating a scalable, capital-light network.
- **Insurance integration**: Partners with 100+ of the nation's top insurance plans, making it the largest mental health provider network in the U.S. [headway.co](https://headway.co/)
- **Software moat**: The platform handles credentialing, billing, and compliance, solving the core reason 70% of therapists don't accept insurance. [headway.co](https://headway.co/about-us)
- **Scale**: With 70,000+ providers and 30M+ sessions, the network effects are significant—more providers attract more patients, and more patients attract more providers.

## Strategic Focus
- **Expanding the provider network**: Continuing to onboard therapists and psychiatrists to increase access and coverage.
- **AI and product innovation**: Actively hiring for roles like "Applied AI Lead" and "Staff Product Manager, AI Patient Experience," indicating a focus on using AI to improve patient matching, scheduling, and care delivery. [headway.co](https://headway.co/careers)
- **Deepening insurance partnerships**: Working with 100+ insurance plans to lower costs for patients and expand in-network access.
- **Scaling the patient experience**: Investing in data science, product management, and engineering to improve the patient journey from search to booking to ongoing care.

## Why Work Here
- **Culture**: 88% of employees say Headway is a great place to work, compared to 57% at a typical U.S. company. [greatplacetowork.com](https://www.greatplacetowork.com/certified-company/7083261)
- **Mission-driven**: Employees are united by the goal of building a new, accessible mental healthcare system. The company highlights that "people are their happiest, healthiest, and best selves when they know their team values them for who they are." [headway.co](https://headway.co/careers)
- **Remote-first with office hubs**: Employees work remotely across the US, with the option to work from offices in New York City, San Francisco, and Seattle. [builtin.com](https://builtin.com/company/headway)
- **Diversity & Inclusion**: The company states a commitment to building a diverse, equitable, and inclusive team, noting it is "a business imperative" and "the right thing to do." [headway.co](https://headway.co/careers)
- **Recognition**: Certified as a Great Place to Work® (88% of employees say it's a great place to work) and ranked #48 on Fortune Best Workplaces in Health Care™ 2025. [greatplacetowork.com](https://www.greatplacetowork.com/certified-company/7083261)
- **Notable perks**: Remote-first culture with optional offices in NYC, San Francisco, and Seattle; strong focus on engineering, data science, and AI roles.

## Sources
1. [headway.co - About Us](https://headway.co/about-us)
2. [headway.co - Careers](https://headway.co/careers)
3. [headway.co - Homepage](https://headway.co/)
4. [builtin.com - Headway Company Profile](https://builtin.com/company/headway)
5. [greatplacetowork.com - Headway Certification](https://www.greatplacetowork.com/certified-company/7083261)

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