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 Strategy Lead (NY Based)

Company: Headway

Location: Remote

Posted Dec 13, 2024

Headways mission is to build a new mental health care system that everyone can access. They aim to make therapy more affordable by helping therapists accept insurance and scaling their practice. Headway is a Series D company with over $325m in funding and has grown to a diverse national network of over 45000 mental healthcare providers. They are seeking a Revenue Strategy Lead to tackle business-critical challenges and drive outcomes.

Senior Product Marketing Manager, Providers

Company: Headway

Location: Remote

Posted Dec 17, 2024

Headways is a new mental health care system aiming to make therapy accessible and affordable for everyone. Founded in 2019, they have grown to a diverse network of over 45,000 providers across all 50 states, serving over 1 million patients. They have raised over $325 million in funding and are looking for a Senior Product Marketing Manager to help scale their product marketing function.

Technical Talent Sourcer (Contract)

Company: Headway

Location: Remote

Posted Dec 17, 2024

Headways mission is to build a new mental health care system that everyone can access. They aim to achieve this by making it easy for therapists to accept insurance and scale their practice. Headway has grown into a diverse national network of over 45,000 mental healthcare providers across all 50 states, serving over 1 million patients. They are seeking a Contract Sourcer for technology functions to identify exceptional talent for their fast-growing teams.

Talent Sourcer (Contract)

Company: Headway

Location: Remote

Posted Dec 17, 2024

Headways mission is to build a new mental health care system that everyone can access. They aim to achieve this by making it easy for therapists to accept insurance and scale their practice. Headway has grown into a diverse national network of over 45,000 mental healthcare providers across all 50 states, serving over 1 million patients. They are currently hiring for a Contract Sourcer position to identify exceptional talent for their sales team.

Associate Principal, Business Development

Company: Headway

Location: Remote

Posted Dec 08, 2024

Headways is a startup founded in 2019 with a mission to build a new mental health care system accessible to everyone. They aim to make it easy for therapists to accept insurance and scale their practice. Headways has grown to a diverse national network of over 45,000 mental healthcare providers across all 50 states, serving over 1 million patients. They are a Series D company with over $325 million in funding from reputable investors. The company is looking for an Associate Principal Business Development to help expand into new geographies, reimagine mental healthcare networks, and bring affordable care to hundreds of thousands of Americans.

Revenue Operations System Developer

Company: Headway

Location: Remote

Posted Dec 11, 2024

Headways is building a new mental health care system that everyone can access by making it easy for therapists to accept insurance and scale their practice. They have grown into a diverse national network of over 45,000 mental healthcare providers across all 50 states and have served over 1 million patients. They are looking for a Revenue Operations Developer to ensure they are the best possible partners to their sales team and design, develop, and maintain complex Salesforce solutions.

Data Engineer

Company: Headway

Location: Remote

Posted Dec 11, 2024

Headways mission is to build a new mental health care system that everyone can access. They aim to make it easy for therapists to accept insurance and scale their practice. Headway has grown into a diverse national network of over 45,000 mental healthcare providers across all 50 states and has served over 1 million patients. They are a Series D company with over $325 million in funding. Headway is looking for a Data Engineer to help them achieve their mission by empowering business decisions and operations at scale.

Associate General Counsel, Corporate and Securities

Company: Headway

Location: Remote

Posted Dec 09, 2024

Headways mission is to build a new mental health care system that everyone can access. They aim to make it easy for therapists to accept insurance and scale their practice. Headway is a Series D company with over $325m in funding. They are looking for an Associate General Counsel Corporate and Securities to join their legal and compliance team. The role involves leading corporate and securities function, debt and equity financing transactions, M&A transactions, maintaining corporate books and records, overseeing stock plan administration, and more. The ideal candidate should have 8+ years of total experience, including 4+ years in-house experience, healthcare-related experience, and be barred in a US state.

Senior Product Designer, Patient Matching

Company: Headway

Location: Remote

Posted Dec 19, 2024

Headway, a mental health tech company founded in 2019, is seeking a Senior Product Designer to join their mission of making mental healthcare accessible and affordable. With over 45,000 providers and 1 million patients served, Headway aims to revolutionize mental healthcare by enabling therapists to accept insurance and scale their practices. The role involves collaborating with the patient matching team to create remarkable patient experiences, using design skills to evolve product vision, and contributing to the company's design system. The ideal candidate should have 5-8 years of experience in product design, a strong portfolio, and a passion for solving mental healthcare issues. Compensation includes a starting salary of $200,000, equity, comprehensive benefits, and flexible work arrangements.

Provider Sales Associate

Company: Headway

Location: Remote

Posted Dec 19, 2024

Headways mission is to build a new mental health care system that everyone can access. They aim to make therapy more affordable and accessible by helping therapists accept insurance and scaling their practice. Headway is a Series D company with over $325m in funding and has grown into a diverse national network of over 45000 mental healthcare providers. They are looking for a Provider Sales Associate to help expand their community of therapists and psychiatrists. The role offers competitive compensation and benefits, including equity compensation, medical dental and vision coverage, HSA FSA, 401K, work from home stipend, therapy reimbursement, 16 week parental leave, carrot fertility annual reimbursement and membership, 13 paid holidays, flexible PTO, and employee assistance program. Headway is committed to full inclusion and provides reasonable accommodations. Employees work remotely across the US with the option to work from offices in New York City and San Francisco.

Associate, Strategy & Operations

Company: Headway

Location: Remote

Posted Dec 11, 2024

Headways mission is to build a new mental health care system that everyone can access. They aim to make it easy for therapists to accept insurance and scale their practice. Headway has grown into a diverse national network of over 45,000 mental healthcare providers across all 50 states, serving over 1 million patients. They are a Series D company with over $325 million in funding. The company is looking for an Associate Strategy and Operations to help lay the groundwork for Operations at Headway.

Internal Communications Lead (NY or SF Based)

Company: Headway

Location: Remote

Posted Dec 04, 2024

Headway is a mental healthcare technology company founded in 2019, aiming to build a new, accessible mental health care system. They've created software that helps people find therapists who accept insurance, addressing the issue of high costs and limited providers. Headway has grown to a network of over 45,000 providers across all 50 states, serving over 1 million patients. They are seeking an experienced Internal Communications Lead to support their 600+ employees and 400+ contingent workers, focusing on employee engagement, cultural principles, and internal communications strategies.

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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