Design Director, Core Insurance & Design Systems

Headway

New York, New York, United States; San Francisco, California, United States; Seattle, Washington, United StatesDesign

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New York, New York, United States; San Francisco, California, United States; Seattle, Washington, United StatesApply1 in 4 people in the US have a treatable mental health condition, but most providers don't accept insurance, making therapy too expensive for most people. Headway’s mission is to fix this by building a new mental healthcare system everyone can access. We started by solving the biggest barrier to care: insurance. The admin work - credentialing, claims, payment reconciliation - is a nightmare. We've automated that.But we're going further. Over 70,000 providers across all 50 states run their practice on our software, serving over 1 million patients. We are building the best tools for therapists to run their entire practice, reimagining the experience of finding a therapist, and investing in the platform foundations to enable this at scale. We aren't just a billing layer; we are becoming the platform where care actually happens.We're a Series D company with $325M+ in funding (a16z, Accel, GV, etc.), looking for exceptional people to help us achieve this mission. We want your time here to be the most meaningful experience of your career. Join us, and help change mental healthcare for the better.At Headway, our mission is to build a new mental healthcare system that everyone can access. Behind the magic for patients to find right and predictable care is our robust design system, insurance platform and internal tools.As the Product Design Director for this team, you will help contribute to our mission by making Headway’s operation more efficient, by building a powerful design system, strategic content design, wildly predictable insurance experience and robust internal tools. In this role, you will lead and continue building a talented team of product designers, design system designers and content designers. You'll be a key partner to other teams, ensuring our design systems empower teams to build cohesive, high-quality experiences at scale.In this role, you will:• Lead the design systems across our products, as well as lead the team defining these systems. You will also be an advocate of design craftsmanship across our product, design, and engineering organizations.• Oversee the foundational experiences including insurance experiences, support experiences and security experiences for our customers.• Manage the internal tooling experiences that helps Headway operate efficiently.• Hire, lead, and coach a team of design system designers, content designers, and product designers responsible for design systems and foundational experiences.Experience we're seeking:• 3+ years of experience leading successful design system or product design teams.• Extensive experience in building and shipping design systems across a variety of systems.• Experience building and scaling a design team.• Great communication and excel in making complex technical details easy to understand.• Value high quality visual design with attention to detail.Compensation and Benefits:**The expected base pay range for this position is $ 249,600 to $312,000 , based on a variety of factors including qualifications, experience, and geographic location. In addition to base salary, this role may be eligible for an equity grant, depending on the position and level.We are committed to offering a comprehensive and competitive total rewards package, including robust health and wellness benefits, retirement savings, and meaningful ownership opportunities through equity. Compensation decisions are made holistically, ensuring fairness and alignment with market benchmarks while recognizing individual contributions and potential.• Benefits offered include:• Equity compensation• Medical, Dental, and Vision coverage• HSA / FSA• 401K• Work-from-Home Stipend• Therapy Reimbursement• 16-week parental leave for eligible employees• Carrot Fertility annual reimbursement and membership• 13 paid holidays each year as well as a Holiday Break during the week between December 25th and December 31st• Flexible PTO• Employee Assistance Program (EAP)• Training and professional development#LI-RJ1We believe a team's strength is in its people, and we cannot achieve this mission without a team that reflects the diversity of this problem – across race, ethnicity, gender, sexuality, age, national origin, religion, family status, disability, military status, and experience. Headway is committed to the full inclusion of all qualified individuals. As part of this commitment, Headway will ensure that persons with disabilities are provided with reasonable accommodations. If reasonable accommodation is needed to participate in the job application or interview process, to perform essential job functions, and/or receive other benefits and privileges of employment, please inform the recruiter when they contact you to schedule your interview.Headway participates in E-Verify. To learn more, click here.A notice to Headway applicants: To protect yourself against phishing and recruitment fraud, please note that Headway only accepts applications through our official careers page at https://headway.co/careers. Headway will never refer you to external websites, ask for payment or personal information, or conduct interviews via messaging apps. All official communication will come from a @findheadway.com email address. If you are contacted by someone claiming to be from Headway via an unofficial channel, please do not share any information and report it as spam.Create a Job AlertInterested in building your career at Headway? Get future opportunities sent straight to your email.

**Create alertApply for this job*indicates a required fieldFirst Name *Last Name *Email *PhoneCountry ***Phone *Resume/CV *Attach AttachGoogle DriveEnter manually Enter manuallyAccepted file types: pdf, doc, docx, txt, rtfCover LetterAttach AttachGoogle DriveEnter manually Enter manuallyAccepted file types: pdf, doc, docx, txt, rtfLinkedIn ProfilePortfolio Link *Are you authorized to work in the United States for any employer? *Select...**Will you now or in the future require visa sponsorship? *Select...**Please select your working location. *Select...**Are you open to relocating for this position? *Select...**In 1-3 sentences, please tell us what brought you here and why you're interested in a role at Headway.I understand and agree that Headway may contact additional references beyond the references you provide to validate your previous employment. *Select...**What is your Legal First Name? *What is your Legal Last Name? *What is your Preferred First Name? *What is your Preferred Last Name? *Headway Custom Demographic QuestionsWe believe that to build the best startup team, we must build a diverse, equitable and inclusive team. We encourage people from all backgrounds to apply to all roles, and we proactively work to design hiring processes that mitigates bias. To help us track the parity in our candidate pipelines and efficacy of our recruiting efforts, please consider answering the following demographic questions. While completion of this survey is required, you will have the option to select “I don't wish to answer” for all questions. Your responses will be used ( in aggregate only ) to help us identify areas of improvement in our process.Your responses will not be linked to your specific application and will not in any way be used in the hiring decision.I identify my gender as *Select...**I identify as transgender *Select...**I identify my sexual orientation as *Select...**I identify my ethnicity as *Select...**Veteran status *Select...**Disability status *Select...****Submit applicationPowered by

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0 views0 applicationsPosted 4/19/2026

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