Head of Engineering (Insurance)

Headway’s mission is a big one – to build a new mental health care system everyone can access. We’ve built technology that helps people find great therapists with the first software-enabled national network of providers accepting insurance. 

1 in 4 people in the US have a treatable mental health condition, but the majority of providers don’t accept insurance, making therapy too expensive for most people. Headway is building a new mental healthcare system that everyone can access by making it easy for therapists to accept insurance and scale their practice. 

Headway was founded in 2019. Since then, we’ve grown into a diverse, national network of over 60,000 mental healthcare providers across all 50 states who run their practice on our software and have served over 1 million patients. We’re a Series D company with over $325m in funding from a16z (Andreessen Horowitz), Accel, GV (formerly Google Ventures), Spark Capital, Thrive Capital, Forerunner Ventures and Health Care Service Corporation.

We want your time here to be the most meaningful experience of your career. Join us, and help change mental healthcare for the better.

About the role:

There is a lot that we're building at Headway, but ensuring that our underlying systems behind our insurance platform reliably power patient, provider, and payer (insurance customer) experiences is mission critical in our efforts to make mental healthcare more accessible and affordable for everyone. As Head of Engineering for the Insurance Group, you will inherit a strong, growing set of engineering pods that deliver critical systems behind benefits and eligibility services, claims, billing infrastructure, payments, and customer support tooling. Your mandate will be to guide and scale this group as Headway grows, ensuring it continues to deliver reliable, secure, and high-impact technology at scale.

Reporting to Headway’s CTO, you’ll be a senior leader within our rapidly growing Engineering Org, responsible for strategic planning, organizational design, and talent development. You’ill set the technical vision and operating model for the group, ensuring our systems evolve to meet the complexity and growth of our marketplace. You’ll be responsible for enabling experiments, accelerating development velocity, and scaling infrastructure that supports one of the most important dimensions of our business: making insurance work seamlessly for providers, patients, and payers.

Your teams will be highly cross-functional, partnering closely with other engineering, product, design, data, customer success, growth, clinical, and other functions to understand the needs of our insurance partners and deliver solutions that redefine how mental healthcare integrates with the broader healthcare ecosystem.

Who you are:

We’re looking for a platform-minded engineering executive who is relationship-obsessed, drives results, and enables teams to deliver with technical excellence. This is an exciting opportunity for a mission-aligned leader to scale one of the most critical engineering groups at Headway and make an immediate impact on the way we expand mental healthcare access.

• Build the vision and roadmap for the next chapter of our Insurance Engineering group, driving company-level objectives and powering best-in-class provider, patient, and payer experiences
• Contribute to the broader company strategy and technical roadmap as a member of the engineering leadership team
• Partner with senior leaders across product, business, data, design, clinical, legal, and compliance to ensure alignment on strategic goals and execution against highly impactful OKRs and KPIs
• Lead and scale multiple engineering pods, ensuring process, architectural, and product alignment across the group
• Develop and grow your managers and team of teams through mentorship, feedback, and career development frameworks
• Recruit and build diverse, high-performing engineering teams that thrive on collaboration and technical excellence
• Shape engineering culture, process, and operating norms as Headway grows from 110 to 150+ engineers in the coming year

Below are additional experiences we think help engineering leaders succeed at Headway:

• You have 8+ years of experience as an engineering leader, including managing managers, with a track record of building and scaling high-performing organizations that deliver business impact through technical innovation
• You have previous experience as a Software Engineer, and a strong technical foundation that allows you to guide and challenge technical decisions
• You are able to see things at a 300-ft view, while also diving deep into highly technical challenges that affect scale, reliability, and user experience
• You have a strong product mindset, having built cross-functional relationships that build trust and enable great user experiences
• You have a passion for building resilient, scalable platforms that unlock growth in new product areas
• It’s a nice to have if you’ve had experience in health tech or with complex platform domains such as insurance, payments, or billing
• BS, MS in Computer Science or related field

Our interview process

After you apply to Headway, here are some details of what to expect during the interview process.

• Initial screen : You’ll connect with someone in recruiting so you can learn more about the team, Headway’s mission and exciting growth, and we can get a better idea of your background. 
• First rounds: You'll meet with an engineering leader on the team to go deeper into your technical and people leadership experiences
• Final rounds : You’ll meet several more team members for one technical and multiple behavioral interviews, leaving you with a fuller picture of what it’s like to work at Headway.
• References and the Offer : Our favorite part of the process! We'll send over all of the details, including specifics on employee equity, and congratulatory messages from excited future team members!

Compensation and Benefits:

• Salary information is based on a single salary target per role, and the starting salary for a Head of Engineering starts at $275,000 and can increase to $380,000 based on industry tenure and experience.
• 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-CA1

We 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 employees work remotely across the US, with the option to work from offices in New York City, San Francisco and Seattle. Headway participates in E-Verify. To learn more, click  here.