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.

Enterprise Marketing Lead

Company: Headway

Location: Remote

Posted Dec 23, 2022

Headway is building a new mental healthcare system that makes it easy for people to find quality in-network mental health care. They have raised over $100 million in funding and are now powering 300,000+ appointments per month.

Talent Acquisition Partner

Company: Headway

Location: Remote

Posted Dec 22, 2022

Headway is building a new mental healthcare system that everyone can access. The company is addressing the issue of cost being a barrier to mental health care by building a software-enabled network of therapists who accept health insurance. They have raised over $100 million in funding and are now powering over 50,000 appointments.

Infrastructure Engineer (Data)

Company: Headway

Location: Remote

Posted Oct 31, 2022

Headway is building a new mental healthcare system that everyone can access. The company is focused on making it easy for therapists to grow their practices and for patients to find quality care they can afford.

Software Engineering (Platform)

Company: Headway

Location: Remote

Posted Nov 21, 2022

Headway is building a new mental healthcare system that everyone can access. The company is addressing the issue of cost being a barrier to mental health care by building a software-enabled network of therapists who accept health insurance.

Senior Content Designer

Company: Headway

Location: Remote

Posted Nov 09, 2022

Headway is building a mental healthcare system that everyone can access. They are addressing the issue of cost being a barrier to mental health care by building a software-enabled network of therapists who accept health insurance. They have raised over $100 million in funding and are now powering 200,000+ appointments per month.

Content Marketing Lead

Company: Headway

Location: Remote

Posted Nov 02, 2022

Headway is building a new mental healthcare system that everyone can access. The company is addressing the issue of cost being a barrier to mental health care by building a software-enabled network of therapists who accept health insurance.

Marketing Associate

Company: Headway

Location: Remote

Posted Dec 23, 2022

Headway is building a new mental healthcare system that makes it easy for people to find quality in-network mental health care. They have raised over $100 million in funding and are now powering 300,000+ appointments per month.

Payer Enrollment Specialist

Company: Headway

Location: Remote

Posted Dec 23, 2022

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

Provider Growth (Sales) Associate

Company: Headway

Location: Remote

Posted Dec 19, 2022

Headway is building a mental healthcare system that everyone can access. They're addressing the issue of cost by creating a software-enabled network of therapists who accept insurance, making it easy for patients to find quality care they can afford.

Software Engineer (Product)

Company: Headway

Location: Remote

Posted Jan 05, 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 raised over $100 million in funding and are now powering 300,000+ appointments per month.

Corporate Communications Lead

Company: Headway

Location: Remote

Posted Dec 19, 2022

Headway is building a mental healthcare system that everyone can access. They are hiring a Corporate Communications Lead to tell the story of Headway and grow their brand.

Remote Psychiatric Mental Health Nurse Practitioner - Texas

Company: Headway

Location: Remote

Posted Jan 04, 2023

Headway is building a new mental healthcare system that provides access to quality care for everyone. They have built a software-enabled network of therapists who accept insurance, making it easy for patients to find affordable care. The company has raised over $100 million in funding and is currently supporting over 12,000 mental health clinicians across the US.

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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