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.

Head of Data Analytics

Company: Headway

Location: Remote

Posted Apr 14, 2023

Headway is a company 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 300,000+ appointments per month. They are looking for a Head of Data Analytics to build a world-class analytics team and drive insights to execute their mission.

Head of Marketing

Company: Headway

Location: Remote

Posted Apr 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. The company has raised over $100 million in funding and is powering 300,000+ appointments per month. They are hiring a Head of Patient & Provider Marketing to grow their brand and drive demand generation for both patients and providers.

Senior Security Engineer

Company: Headway

Location: Remote

Posted Apr 13, 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.

Remote Psychiatric Mental Health Nurse Practitioner - Georgia

Company: Headway

Location: Remote

Posted Apr 08, 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, including insurance handling, flexible scheduling, and patient referrals. Headway aims to streamline the care process, verify insurance benefits instantly, and provide customized support to clinicians and patients.

Manager, Strategy & Operations

Company: Headway

Location: Remote

Posted Apr 05, 2023

Headway is building a new mental healthcare system that everyone can access, aiming to remove historic barriers faced by mental health providers, payers, and patients. The company has made significant progress, powering over 300,000 appointments per month and raising over $100 million in funding. The role of a Manager, Strategy & Operations, involves designing and implementing solutions, collaborating with cross-functional teams, and building scalable systems to support Headway's growth and impact on affordable mental healthcare.

CX Program Manager, Tools & Processes

Company: Headway

Location: Remote

Posted Apr 26, 2023

None Found

Associate, Strategy & Operations

Company: Headway

Location: Remote

Posted Apr 05, 2023

Headway is a startup 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 having therapists accept health insurance. The company has raised over $100 million in funding and is currently powering 300,000+ appointments per month. They are looking for an Associate, Strategy & Operations, to help build the operations team and support primary clients.

Associate General Counsel

Company: Headway

Location: Remote

Posted Apr 18, 2023

Headway is a mental healthcare system aiming to make quality care accessible by removing barriers faced by providers, payers, and patients. They are addressing the issue of high-cost therapy by partnering with therapists who accept health insurance, making appointments more affordable. The company has grown rapidly, powering over 300,000 appointments per month and raising over $100 million in funding. They are seeking an Associate General Counsel to provide legal advice and support the company's growth.

Head of Payer Operations

Company: Headway

Location: Remote

Posted Apr 14, 2023

Headway is a mental healthcare startup that aims to make quality, affordable therapy accessible to everyone. They have built a software-enabled network of therapists who accept health insurance, enabling them to grow their practices and patients to find quality care they can afford. Headway is seeking an operational leader to build and scale the operational engine for insurance billing, as they scale towards their billionth appointment. The role involves defining and implementing Headway's long-term strategy for insurance revenue collection, leading a world-class operational team, and navigating external relationships with health plan partner organizations.

Business Development Associate, Payer Partnerships

Company: Headway

Location: Remote

Posted Apr 10, 2023

Headway is a mental healthcare company that aims to make quality care accessible to everyone. They have built a network of therapists who accept health insurance, addressing the primary barrier of cost. The company has raised over $100 million in funding and is currently powering 300,000+ appointments per month. They are seeking a Business Development Associate to lead market analysis, healthcare research, and build sales infrastructure. The ideal candidate will have 3+ years of experience in consulting or banking, be resourceful, operationally excellent, and thrive in ambiguity. Headway values diversity and inclusion, with employees working remotely across the US and the option to work from their NYC HQ.

Senior Associate, Strategy & Operations

Company: Headway

Location: Remote

Posted Apr 18, 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 providers, payers, and patients. The company has launched and is powering over 300,000 appointments per month, having raised over $100 million in funding. The role involves designing and building foundations for various initiatives within the Patient Operations function, driving the build and implementation of scalable products and processes, and collaborating with cross-functional teams to optimize patient benefits performance.

Operations Manager

Company: Headway

Location: Remote

Posted Apr 05, 2023

Headway is building a new mental healthcare system that everyone can access, aiming to remove historic barriers faced by mental health providers, payers, and patients. The company has made significant progress, powering over 300,000 appointments per month and raising over $100 million in funding. The Operations Manager role involves designing and building foundations for various initiatives, collaborating cross-functionally, and analyzing data to drive progress and improve processes.

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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