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.

Remote Psychiatric Mental Health Nurse Practitioner - Florida

Company: Headway

Location: Remote

Posted Jun 06, 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 over 400,000 appointments per month. They've raised over $100 million in funding and aim to scale their vision. Headway also supports mental health clinicians in growing their practices and reaching their goals.

Remote Licensed Mental Health Therapist - Florida

Company: Headway

Location: Remote

Posted Jun 06, 2023

Headway is building a new mental healthcare system that aims to make quality in-network mental health care more accessible by removing barriers faced by mental health providers, payers, and patients. The company has built a software-enabled network of therapists who accept health insurance, allowing 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 their practices, including insurance handling, flexible scheduling, and marketing support. Headway also provides live support, insurance verification, and a flexible service for remote patient consultations.

Head of Demand Generation

Company: Headway

Location: Remote

Posted May 01, 2023

None Found

Senior Associate, Strategy & Operations

Company: Headway

Location: Remote

Posted Jun 07, 2023

Headway is a mental healthcare company that aims to make quality care accessible by removing financial barriers. They have built a network of therapists who accept insurance, enabling patients to afford therapy. The company is currently scaling its operations and has raised over $100 million in funding. They are seeking a candidate with operations experience to lead the Patient Operations team, focusing on improving the Patient Benefits engine. The role involves designing and implementing solutions to enhance patient experience, collaborating with various teams, and optimizing performance with health plan partners. The ideal candidate should be a self-starter, data-driven, collaborative, and a systems thinker with a passion for team building.

Partnership Strategy & Success Lead

Company: Headway

Location: Remote

Posted Jun 06, 2023

Headway is building a new mental healthcare system that everyone can access, aiming to make quality in-network mental health care more accessible by removing barriers faced by mental health providers, payers, and patients. The company has raised over $100 million in funding and is currently powering 400,000+ appointments per month. The Partnership Strategy Implementation & Operations Lead role is a front-line position in rewiring mental healthcare in America, involving strategic implementation, operations, and expansion across payer partners.

Head of Data Analytics

Company: Headway

Location: Remote

Posted May 10, 2023

None Found

Creative Director

Company: Headway

Location: Remote

Posted May 23, 2023

Headway is a mental healthcare company that aims to make quality, affordable care accessible to everyone. They have built a network of therapists who accept health insurance, enabling patients to find quality care they can afford. The company has raised over $100 million in funding and is now powering 300,000+ appointments per month. They are seeking a founding Creative Director to define and evolve their brand visual identity, build the creative discipline, and establish a process. The ideal candidate will have 8+ years of creative team experience, a strong portfolio, and a passion for their mission to improve mental health care.

Operations Manager, Clinical Team

Company: Headway

Location: New York City, NY

Posted May 19, 2023

None Found

Executive Assistant

Company: Headway

Location: Remote

Posted Jun 08, 2023

Headway is building a new mental healthcare system to make quality in-network mental health care more accessible and affordable. They have raised over $100 million in funding and are powering 400,000+ appointments per month. They are hiring an Executive Assistant to support their VP of Engineering in managing their expansive organization.

Senior Associate, Strategy & Operations

Company: Headway

Location: Remote

Posted Jun 07, 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 400,000+ appointments per month.

Provider Growth (Sales) Manager

Company: Headway

Location: Remote

Posted May 09, 2023

None Found

Business Operations & Strategy Lead

Company: Headway

Location: Remote

Posted May 26, 2023

Headway is a mental healthcare startup building a software-enabled network of therapists who accept health insurance, making mental health care more affordable and accessible. They have launched in April 2019 and are powering 300,000+ appointments per month. The company has raised over $100 million in funding from prominent investors. The role of the Business Operations & Strategy team is to drive mission-critical outcomes, cultivate world-class entrepreneurial leaders, and own complex problems.

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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