Head of Engineering (Platform)

Headway•San Francisco, NY

23h•$275,000 - $380,000

About The Position

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 Platform Group (also know as our Insurance Group), you'll be the first hire in a new altitude of leadership, inheriting 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’ll 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.

Requirements

You have 8+ years of experience as an engineering leader, including managing engineering directors/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

Nice To Haves

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

Responsibilities

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 150 to 250+ engineers in the coming year

Benefits

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