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-func