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.

Technical Talent Sourcer (Contract)

Company: Headway

Location: Remote

Posted Jan 21, 2025

Headway, a mental health tech company founded in 2019, aims to revolutionize mental healthcare by making it accessible and affordable. With over 45,000 providers and 1 million patients served, Headway is expanding its national network. The company is currently hiring a Tech Contract Sourcer to source top talent for tech roles, supporting the fast-growing teams. The role involves using tools like LinkedIn Recruiter, Gem, and Greenhouse, and is compensated at $55/hour. Headway values diversity and inclusion, offering remote work across the US with offices in NYC and San Francisco.

Sales Recruiter

Company: Headway

Location: Remote

Posted Jan 22, 2025

Senior Product Security Engineer

Company: Headway

Location: Remote

Posted Jan 23, 2025

Headway, a mental healthcare company founded in 2019, is seeking an early member for its Trust team. The role involves partnering with product and engineering teams to ensure secure design and development of new features, enhancing automated tooling for scalable product security, and assisting in ongoing security operations. The ideal candidate has 5+ years of security or software engineering experience, strong cross-functional skills, technical depth, and a mission-driven attitude. Headway offers a competitive salary, comprehensive benefits, and a commitment to diversity and inclusion.

Senior Business Recruiter

Company: Headway

Location: Remote

Posted Jan 21, 2025

Headway, a mental health care company founded in 2019, aims to revolutionize the mental health system by making therapy accessible to all. With over 45,000 providers across 50 states and serving over 1 million patients, Headway is backed by significant funding from top venture capital firms. The company is currently seeking an experienced Business Recruiter to join their growing team. The ideal candidate will have 7+ years of full-cycle recruiting experience in high-growth, tech-enabled companies, and a strategic, data-driven approach to hiring. The role involves partnering with hiring managers, developing DEI sourcing strategies, and contributing to cross-functional projects. Compensation ranges from $129,600 to $162,000 based on location, with comprehensive benefits including equity, health coverage, and flexible PTO.

Senior Product Marketing Manager, Providers

Company: Headway

Location: Remote

Posted Jan 23, 2025

Headway, a mental health tech company founded in 2019, aims to revolutionize mental healthcare by building a national network of insurance-accepting therapists. With over 45,000 providers and 1 million patients served, Headway is backed by $325m in funding from top investors. The company is seeking a Senior Product Marketing Manager for Providers to scale their product marketing function, focusing on product messaging, launches, and sales enablement content. The ideal candidate will have 7-10 years of product marketing experience, preferably in health tech, and a strong track record of driving results. Compensation ranges from $168,000 to $210,000 based on location. Benefits include equity, medical coverage, work-from-home stipend, therapy reimbursement, and more.

Senior Product Manager, Provider Support Experience

Company: Headway

Location: Remote

Posted Jan 21, 2025

Headway, a mental health tech company founded in 2019, is seeking a Senior Product Manager to enhance its customer support experience. The role involves building new support channels, crafting efficient tools with AI, and collaborating with cross-functional teams. The ideal candidate should have 5+ years of CX experience, be customer-obsessed, data-driven, collaborative, and comfortable with ambiguity. The starting salary is $200,000 with comprehensive benefits including equity, health coverage, 401K, work-from-home stipend, therapy reimbursement, and more. Headway values diversity and inclusion, offering remote work across the US with offices in NYC and San Francisco.

Engineering Manager (Provider CX & Group Practice Tooling)

Company: Headway

Location: Remote

Posted Jan 23, 2025

Headway, a mental health tech company founded in 2019, aims to revolutionize mental healthcare by making it accessible to all. With over 45,000 providers and 1 million patients served, Headway is expanding its engineering team. They're seeking experienced engineering leaders to join newly formed teams focused on tooling for Group Practices and delivering best-in-class support experiences. The ideal candidate will have 3-5+ years of software engineering and management experience, a strong technical foundation, and a product mindset. Headway offers competitive compensation, comprehensive benefits, and a commitment to diversity and inclusion.

Government Programs Compliance Lead

Company: Headway

Location: Remote

Posted Jan 21, 2025

Headway, a mental health tech company founded in 2019, is seeking a Government Compliance Lead. The role involves developing and implementing a Medicare and Medicaid compliance program, providing technical and regulatory guidance, and fostering a culture of compliance. The company, with over $325m in funding, has a national network of 45,000 mental healthcare providers and has served over 1 million patients. The ideal candidate should have 5+ years of compliance experience, deep knowledge of healthcare regulations, and excellent communication skills.

Privacy and Regulatory Counsel

Company: Headway

Location: Remote

Posted Jan 23, 2025

Headway, a mental healthcare company founded in 2019, aims to revolutionize the mental health system by making therapy accessible to all. With over 45,000 providers across 50 states and serving over 1 million patients, Headway is backed by significant funding. The company is seeking a Privacy and Regulatory Counsel with 5+ years of legal experience, preferably in healthcare or tech, to ensure compliance and quality. The role involves advising on privacy, security, anti-fraud, open-source software, and more. The position offers competitive compensation, benefits, and opportunities for growth.

Engineering Manager (Patient Growth)

Company: Headway

Location: Remote

Posted Jan 22, 2025

Headway is a mental healthcare technology company founded in 2019, aiming to create an accessible and affordable mental healthcare system. They've built a platform that connects people with therapists who accept insurance, serving over 1 million patients across 50 states. With over $325m in funding, Headway is currently seeking an engineering leader to grow and manage teams, focusing on high-impact product development and platform integration. This role offers the opportunity to shape patient experiences, directly impacting lives and transforming healthcare.

Senior Technical Recruiter

Company: Headway

Location: Remote

Posted Jan 21, 2025

Headway, a mental health tech company founded in 2019, aims to revolutionize mental healthcare by making it accessible and affordable. With over 45,000 providers across all 50 states and serving over 1 million patients, Headway is backed by significant funding from top venture capital firms. The company is currently hiring a Senior Technical Recruiter to join their growing team, focusing on technical roles in Engineering, Product, and Design. The ideal candidate will have extensive recruiting experience in high-growth tech companies, a strategic mindset, and a commitment to diversity, equity, and inclusion. Compensation ranges from $129,600 to $162,000 based on location, with comprehensive benefits including equity, health coverage, and flexible PTO.

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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