Head of Engineering, Headway
Platform
$312-390k
+ Equity Compensation
Therapist-by-insurance marketplace
Open for applications
Therapist-by-insurance marketplace
1001+ employees
Open for applications
$312-390k
+ Equity Compensation
1001+ employees
Company mission
To build a new mental healthcare system, rewired for access and affordability.
Role
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
- 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
- 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
What the job involves
- 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
- 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
Application 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!
Our take
1 in 4 US citizens are currently living with treatable mental health conditions, however, a vast majority of people are unable to access the care they need, the primary reason being cost. Headway connects clients with therapists who accept insurance as payment and provides independent practitioners with the tools and resources needed to serve their patients and manage administrative workloads.
Headway’s concept is timely, with national mental health under particular strain following events from the past few years. The company facilitates over 600,000 appointments per month and has attracted backing from the likes of Accel and Google Ventures.
Covering 16 states and the District of Columbia, the company intends to broaden its presence across the US with over $325M in funding behind it. This is a crucial avenue for further growth, as medical care deserts across the US mean the potential market is vast.
Freddie
Company Specialist at Welcome to the Jungle
Insights
64% employee growth in 12 months
Company
Funding (last 2 of 6 rounds)
Jul 2024
$100m
LATE VC
Oct 2023
$125m
SERIES C
Total funding: $327m
Company HQ
Tribeca, New York, NY
Leadership
Andrew Adams
(Founder & CEO)Prior to founding Headway in 2017, Andrew was a Product Analyst at Spring Inc.
Salary benchmarks
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