Senior Staff Software Engineer, Headway
Payer
$264-330k
+ Equity
Therapist-by-insurance marketplace
Open for applications
Therapist-by-insurance marketplace
1001+ employees
Open for applications
$264-330k
+ Equity
1001+ employees
Company mission
To build a new mental healthcare system, rewired for access and affordability.
Role
Who you are
- End-to-End Product Builder: You care just as much about the API architecture as you do the user experience. You seamlessly context-switch between backend logic and frontend state management
- Owns Outcomes, Not Tasks: You've been handed ambiguous problems and turned them into shipped software. You know how to define the solution, pull in the right people across teams, and keep things moving when priorities shift
- Sets the Technical Standard: You make technical decisions that optimize for maintainability and scale, not just shipping speed. You proactively improve your team's engineering velocity - whether that's refining tooling, improving automation, or establishing patterns that prevent entire categories of bugs
- Mentor by Default: You pull engineers into design discussions without being asked. Your code reviews teach, not just gatekeep. You make sure knowledge gets shared across the team, not siloed in one person's head
- Ships Fast, Iterates Faster: You can move from problem statement to working solution quickly. You'd rather ship a good v1 this week than a perfect v1 next month. Real feedback from therapists and patients is worth more than another round of design review
- Quick Study in Complex Domains: Healthcare is a maze of payers, regulations, and exceptions. You don't need prior healthcare experience, but you need to be someone who dives into unfamiliar domains and builds a working mental model fast
- Motivated by Impact: You want your engineering skills applied to problems that matter. Mental healthcare access is broken in America, and you want to be part of fixing it
- Communicates with Precision: Whether it's a Slack thread, a design doc, or a cross-team meeting, you communicate clearly and concisely. You know that great engineering is wasted if you can't bring people along
- AI Frontier Tinkerer: You don't just use AI tools - you push their limits. You've experimented with applying LLMs to real workflows, whether that's code generation, operational automation, or developer tooling. You bring a builder's mindset: what can we automate, what should stay human, and how do we ship it responsibly in healthcare?
What the job involves
- Payers & Outcomes at Headway sits at the intersection of ML, clinical quality, and trust
- You’re building the intelligent systems that protect the integrity of our network — spotting risk, surfacing quality signals, and giving providers real-time feedback so they can deliver great care
- Clinical Feedback: Architect the LLM-powered systems that review clinical documentation at scale and deliver helpful, real-time feedback to providers. Turn a traditionally painful audit process into a coaching experience — and scale it across the entire network
- Detecting Risk in Healthcare Claims: Design the ML/LLM systems that spot patterns of inappropriate billing, over-utilization, and low-quality care across millions of appointments and claims. Translate those signals into clear feedback for providers and transparent reporting for our insurance partners
- Measuring & Elevating Clinical Quality: Help build the systems that systematically review every prescriber in our network against clinical quality standards — so we can measure, improve, and defend the quality of care Headway delivers. The stakes are real: our most recent launch reviews clinical notes and nudges providers to put a safety plan in place when a patient shows signs of suicidal risk — a system projected to save roughly 1,000 lives a year
- Patient Needs & Provider Fit: Crack the “one size fits all” problem. Build ML systems that understand how complex a patient’s needs are and match them to providers best suited to help — so every patient gets the right care and every provider operates at their best
- Trustworthy AI in Healthcare: Champion how Headway evaluates and iterates on AI systems. Build the evaluation frameworks, optimization loops, and observability that keep LLM-powered features reliable and safe in a regulated environment
- Technical Foundations & Mentorship: Set the technical bar for the Payers & Outcomes group — ~12 engineers today, growing to 30–50 by end of year. Lay the architectural foundations other teams will build on, and raise the whole group’s engineering craft as it scales
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 round: You'll meet with an engineer on the team to do some live coding and learn more about the engineering team
- Final rounds: You’ll meet several more team members for technical and non-technical interviews and leave 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.
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