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.

Revenue Support Associate

Company: Headway

Location: Remote

Posted Sep 05, 2024

Headway is a company that aims to build a new mental health care system, making it easy for therapists to accept insurance and scale their practice. They are looking for a Revenue Support Associate to support their sales team and ensure timely responses to requests.

Sales Manager

Company: Headway

Location: Remote

Posted Sep 08, 2024

Headway is a company that aims to build a new mental health care system, making it easy for therapists to accept insurance and scale their practice. They are looking for a Sales Manager to expand their therapist network across the US.

Senior Data Scientist

Company: Headway

Location: Remote

Posted Sep 03, 2024

Headway is a company that aims to build a new mental health care system, making it easy for therapists to accept insurance and scale their practice. They are seeking a Senior Data Scientist to join their growing team and help drive their science and ML efforts.

Engineering Manager (Groups & Provider Engagement)

Company: Headway

Location: Remote

Posted Sep 21, 2024

Headway is a company that aims to build a new mental health care system, making it easy for therapists to accept insurance and scale their practices. They are looking for an engineering leader to help build and grow their engineering team.

Creative Operations Lead

Company: Headway

Location: Remote

Posted Sep 18, 2024

Headway is a company that aims to build a new mental health care system, making it easy for therapists to accept insurance and scale their practice. They are looking for a Creative Operations Lead to own and evolve their creative and production working model.

Senior Backend Software Engineer

Company: Headway

Location: Remote

Posted Sep 16, 2024

Headway is a company that aims to build a new mental health care system, making it easy for therapists to accept insurance and scale their practices. They are looking for experienced engineers to join their team and help change mental healthcare for the better.

Senior Fullstack Software Engineer

Company: Headway

Location: Remote

Posted Sep 10, 2024

Headway is a company that aims to build a new mental health care system, making it easy for therapists to accept insurance and scale their practice. They are looking for experienced engineers to join their team and help change mental healthcare for the better.

Lead, Strategy & Operations

Company: Headway

Location: Remote

Posted Sep 06, 2024

Headway is a company that aims to build a new mental health care system, making it easy for therapists to accept insurance and scale their practice. They are looking for an Operations Lead to help build and operate various workflows that support their primary clients.

Senior Product Manager, Patient Experience

Company: Headway

Location: Remote

Posted Sep 19, 2024

Headway is a company that aims to build a new mental health care system, making it easy for therapists to accept insurance and scale their practice. They are looking for a Senior Product Manager to shape the patient experience and increase affordable access to mental healthcare.

Medical/Clinical Director, Partnership Strategy

Company: Headway

Location: Remote

Posted Sep 07, 2024

Headway is a company that aims to build a new mental health care system, making it easy for therapists to accept insurance and scale their practice. They are looking for a Clinical Director to support their health plan relationships and product strategy.

Head of Clinical Operations

Company: Headway

Location: Remote

Posted Sep 12, 2024

Headway is a company that aims to build a new mental health care system, making it easy for therapists to accept insurance and scale their practice. They are looking for a Head of Clinical Operations to build and lead a high-performing team, and offer competitive compensation and benefits.

Senior Security Software Engineer

Company: Headway

Location: Remote

Posted Sep 09, 2024

Headway is a startup that aims to build a new mental health care system, making it easy for therapists to accept insurance and scale their practice. The company is looking for a Security Engineer to join its founding team, with a focus on building and implementing tools for infrastructure, application, and data security.

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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