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.

Product Manager, Network

Company: Headway

Location: Remote

Posted Oct 13, 2022

Headway is building a new mental healthcare system that everyone can access. The company has raised over $100 million in funding and is now powering 200,000+ appointments per month. They are looking for a data-minded product manager to build the foundational system for their network.

Customer Experience Associate

Company: Headway

Location: Remote

Posted Oct 01, 2022

Headway is building a mental healthcare system that everyone can access. They are addressing the issue of cost 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.

Business Development and Strategy Associate

Company: Headway

Location: Remote

Posted Oct 19, 2022

Headway is building a mental healthcare system that everyone can access. The company has raised over $100 million in funding and is now powering 200,000+ appointments per month. The role of Business Development and Strategy Associate is to accelerate the company's BD efforts and build a mental healthcare system everyone can access.

Data Analyst

Company: Headway

Location: Remote

Posted Oct 03, 2022

Headway is building a new mental healthcare system that everyone can access. The company is working to solve the biggest problems in mental health care today (access and affordability) by providing a software-enabled network of therapists who accept health insurance.

Senior Product Designer, Provider

Company: Headway

Location: Remote

Posted Sep 22, 2022

Headway is building a mental healthcare system that everyone can access. The company aims to make it easy for therapists to grow their practices and for patients to find affordable care. They have raised over $100 million in funding and are now powering 200,000+ appointments per month.

Remote Psychiatric Mental Health Nurse Practitioner - New York State

Company: Headway

Location: Remote

Posted Oct 05, 2022

Headway is building a mental healthcare system that everyone can access. They provide a software-enabled network of therapists who accept health insurance, making it easy for patients to find quality care they can afford.

Head of Product

Company: Headway

Location: Remote

Posted Sep 25, 2022

Headway is building a 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.

Quality Assurance Manager

Company: Headway

Location: Brooklyn NY

Posted Oct 22, 2022

Headway is building a new mental healthcare system that everyone can access. The company is looking for an experienced QA Manager to lead a team of QA specialists and help scale their customer service infrastructure.

Customer Experience BPO Manager

Company: Headway

Location: Remote

Posted Oct 15, 2022

Headway is building a new mental healthcare system that everyone can access. The company is looking for an experienced BPO manager to oversee relationships with BPO partners and drive results.

Head of Strategic Finance

Company: Headway

Location: Remote

Posted Oct 14, 2022

Headway is building a new mental healthcare system that everyone can access. The company has raised over $100 million in funding and is now powering 200,000+ appointments per month. They are looking for a Head of Strategic Finance to drive their financial model and shape their growth trajectory.

Product Manager, Network Expansion

Company: Headway

Location: Remote

Posted Oct 18, 2022

Headway is building a mental healthcare system that everyone can access. They are addressing the issue of cost 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.

Remote Licensed Mental Health Therapist - New York State

Company: Headway

Location: Remote

Posted Oct 05, 2022

Headway is building a mental healthcare system that everyone can access. They provide a software-enabled network of therapists who accept health insurance, making it easy for patients to find quality care they can afford.

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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