Jobs at Headway

Positions 1,960

Headway is a Seattle‑based fintech company that delivers AI‑driven personal financial planning tools. Known for rapid product iterations and a commitment to open‑source AI research, it now serves over 1 million users worldwide.

Headway hires software engineers, data scientists, product managers, UX designers, and DevOps specialists. Teams work with Python, Go, React, TensorFlow, and PyTorch, and engineers participate in quarterly hackathons and high‑velocity delivery cycles.

Job Transparency’s listings give real‑time salary benchmarks, employee satisfaction scores, and interview transparency. By comparing Headway’s compensation to industry norms, you can negotiate confidently and understand the company’s culture before applying.

Senior Accountant

Company: Headway

Location: Remote

Posted Feb 17, 2023

Headway is a mental healthcare company building a software-enabled network of therapists who accept health insurance, making mental health care more affordable and accessible. They have raised over $100 million in funding and are powering 300,000+ appointments per month. They are looking for a Senior Accountant to help establish financial operations that will scale with the growth of the company.

Customer Success Lead

Company: Headway

Location: Remote

Posted Feb 28, 2023

Headway is a mission-driven company building a new mental healthcare system to make quality in-network mental health care accessible. They aim to address the issue of high costs by partnering with insurance providers and offering affordable therapy options. The company has already powered over 300,000 appointments per month and has raised over $100 million in funding. They are looking for a Customer (Health Plan) Success Lead to support their growth and innovation with strategic partners.

Infrastructure Engineer

Company: Headway

Location: Remote

Posted Feb 20, 2023

Headway is building a new mental healthcare system that aims to make quality care more accessible and affordable. The company has raised over $100 million in funding and is currently powering 300,000+ appointments per month. The infrastructure engineering team at Headway is responsible for building and maintaining the company's AWS infrastructure, automated deploy processes, and developer experience.

Remote Psychiatric Mental Health Nurse Practitioner - Virginia

Company: Headway

Location: Remote

Posted Feb 17, 2023

Headway is a mental healthcare system aiming to make quality in-network mental health care accessible by removing barriers faced by providers, payers, and patients. The company has built a software-enabled network of therapists who accept health insurance, enabling therapists to grow their practices and patients to find affordable care. Headway has raised over $100 million in funding and supports thousands of mental health clinicians across the US. The company offers tools and resources for mental health practitioners to run private practices, including insurance handling, flexible scheduling, and patient referrals.

HR Business Partner

Company: Headway

Location: Remote

Posted Mar 04, 2023

Headway is building a new mental healthcare system to make quality care affordable and accessible. They have raised over $100 million in funding and are powering 300,000+ appointments per month. They are looking for an HR Business Partner to develop their talent strategy and support their employees.

Clinical Lead (Clinician Engagement and Education)

Company: Headway

Location: Remote

Posted Feb 27, 2023

Headway is building a new mental healthcare system that makes it easy for people to find quality in-network mental health care. They have built a software-enabled network of therapists who accept health insurance, making it possible for patients to find quality care they can afford.

Salesforce & Marketo Admin

Company: Headway

Location: Remote

Posted Mar 01, 2023

Headway is a mental healthcare company that aims to make quality care accessible and affordable. They have built a software-enabled network of therapists who accept health insurance, powering over 300,000 appointments per month. Headway is rapidly expanding and seeks a Salesforce and Marketo Admin to define and execute a best-in-class cloud stack for various teams. The role involves designing and iterating platform integrations, partnering with senior leaders, and developing cloud reporting for data-informed decisions.

Sales Manager

Company: Headway

Location: Remote

Posted Mar 01, 2023

Headway is building a new mental healthcare system to make quality care more accessible and affordable. They have raised over $100 million in funding and are powering 300,000+ appointments per month. They are looking for a Sales Manager to join their rapidly scaling team and expand their therapist network across the US.

Security Engineer

Company: Headway

Location: Remote

Posted Feb 22, 2023

Headway is a startup building a new mental healthcare system that aims to make quality in-network mental health care more accessible. They are removing historic barriers faced by mental health providers, payers, and patients. The company has raised over $100 million in funding and is currently powering 300,000+ appointments per month. The role of the founding Security Engineering team is to design and implement a next-generation security program for the company's business and systems.

Remote Psychiatric Mental Health Nurse Practitioner - New York State

Company: Headway

Location: Remote

Posted Mar 05, 2023

Headway is a mental healthcare system aiming to make quality in-network mental health care accessible by removing barriers faced by providers, payers, and patients. They focus on affordability, as 1 in 4 people in the US have treatable mental health conditions but don't receive care due to cost. Headway has built a software-enabled network of therapists accepting health insurance, supporting 300,000+ appointments per month. They've raised over $100 million in funding and offer resources for mental health practitioners to grow their private practices.

Group Product Manager, Platform

Company: Headway

Location: Remote

Posted Feb 25, 2023

Headway is a mental healthcare company building a new system for easy access to quality in-network care. They are addressing the issue of high costs by partnering with therapists who accept health insurance, making it possible for patients to afford care. The company has raised over $100 million in funding and is powering 300,000+ appointments per month. They are looking for a GPM of their Insurance Platform team to lead the development of the core platform and APIs, and drive major company-wide initiatives.

CX Workforce Management Lead

Company: Headway

Location: Remote

Posted Mar 04, 2023

Headway is building a new mental healthcare system that aims to make quality care more accessible and affordable. The company has raised over $100 million in funding and is currently powering 300,000+ appointments per month. They are looking for an experienced Workforce Management Lead to help shape the customer experience and optimize staffing.

Frequently Asked Questions

What is it like to work at Headway?
Headway fosters a culture of transparency, continuous learning, and rapid iteration. Employees enjoy flexible remote options, quarterly skill‑share sessions, and a data‑driven approach to product decisions. The team values diversity and encourages cross‑functional collaboration, so you’ll often find yourself working closely with designers, data scientists, and marketing to launch features fast.
What types of positions are available at Headway?
Headway’s 580 openings cover software engineering (frontend, backend, full‑stack), data science, product management, UX/UI design, DevOps, QA, and customer success. Roles span from junior developers to senior architects, and many positions emphasize experience with cloud platforms, machine learning pipelines, and scalable web services.
How can I stand out as an applicant for Headway?
Showcase concrete achievements, quantify impact, and align your portfolio with Headway’s product focus. Submit code samples on GitHub that demonstrate clean architecture and test coverage, contribute to open‑source projects relevant to AI, and prepare case studies that illustrate end‑to‑end feature delivery. Highlight your familiarity with Python, Go, and React, and express enthusiasm for participating in hackathons and cross‑team initiatives.

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