1 in 4 people in the US have a treatable mental health condition, but most providers don't accept insurance, making therapy too expensive for most people. Headway’s mission is to fix this by building a new mental healthcare system everyone can access. We started by solving the biggest barrier to care: insurance. The admin work - credentialing, claims, payment reconciliation - is a nightmare. We've automated that.

But we're going further. Over 75,000 providers across all 50 states run their practice on our software, serving over 1 million patients. We are building the best tools for therapists to run their entire practice, reimagining the experience of finding a therapist, and investing in the platform foundations to enable this at scale. We aren't just a billing layer; we are becoming the platform where care actually happens.

We're a Series D company with $325M+ in funding (a16z, Accel, Spark Capital, etc.), looking for exceptional people to help us achieve this mission. We want your time here to be the most meaningful experience of your career. Join us, and help change mental healthcare for the better.

Staff Software Engineer (Insurance)

The Work

The Insurance team is the backbone of Headway's business. We deliver the two core promises of the platform: affordable therapy covered by insurance for patients, and a simple way to run a therapy practice for providers. Every appointment on Headway flows through systems our team owns — from identifying whether a patient is eligible, to estimating their cost, to matching them with a provider, to submitting a clean claim.

This is a deep and wide problem. We operate across all 50 states, 1,000+ payers, and millions of appointments every month. There's a lot of data to make sense of and signal to find in the noise. As Headway's network grows — more patients, more providers, more payers — the accuracy, reliability, and automation of these systems become the difference between a business that scales and one that doesn't.

As a staff engineer in the group, you will lead design and implementation of the systems that power Headway's insurance operations — patient identification, pricing estimates, provider matching, and claims. Build data-intensive, ML-powered platforms that serve patients and providers and learn from every visit, mentor engineers, and write high-impact code at the intersection of healthcare data and payer operations.

Some examples of what that work looks like in practice:

• Building a new ML model that lifted price estimate accuracy by 10+ percentage points, getting tens of thousands of patients a better estimate ahead of their first session

• An OCR pipeline to read patient insurance cards, automate eligibility checks, and run ML models to detect complex insurance arrangements — improving onboarding and first-claim success rates

• A claims AI agent that reviews denied claims, identifies root causes, and resubmits autonomously — recovering hundreds of thousands of dollars and proving we can build self-healing systems at scale

• A human-in-the-loop automation that transformed a 20-step manual credentialing process in Google Sheets into an average of 2 days and 1 task — with a record of 6 seconds start to finish — enabling providers to onboard faster and expand their reach to new patients

Our Stack

• Languages: TypeScript, Python 3

• Frontend: React, Remix, Next.js

• Backend & Storage: FastAPI, SQLAlchemy, Postgres, Redis, Snowflake

• Infrastructure: AWS, Temporal, Kafka

• Ops: Datadog, Sentry, PagerDuty

• AI Tools: Cursor, Claude, Gemini, Eddy (our in-house cloud agent harness)

Who You Are

• A platform thinker. You build for the teams behind you, not just the immediate use case. You create abstractions that let others move faster and more safely.

• Drawn to signal in messy data. Payer rules vary by state, plan, and policy. You find the structure in the noise and build systems that reason about it reliably.

• Hands-on. You write code where leverage is highest and hold yourself to the same bar you hold others.

• Own 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.

• Communicate with precision. Whether it's a design doc, a Slack thread, or a cross-team meeting — you bring people along.

Our Interview Process

• Initial screen: You'll connect with someone in recruiting to learn more about the team, Headway's mission, and our growth — and we'll get a better sense of your background.

• Tech & Team Fit round: AI Coding and Hiring Manager Chat.

• Final rounds: You'll meet several 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 the details, including specifics on employee equity, and congratulatory messages from excited future teammates. 

Compensation and Benefits:

The expected base pay range for this position is $224,000-$336,000 based on a variety of factors including qualifications, experience, and geographic location. In addition to base salary, this role may be eligible for an equity grant, depending on the position and level.

We are committed to offering a comprehensive and competitive total rewards package, including robust health and wellness benefits, retirement savings, and meaningful ownership opportunities through equity. Compensation decisions are made holistically, ensuring fairness and alignment with market benchmarks while recognizing individual contributions and potential.

• 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

[To be included if role is bonus eligible][Other compensation includes: discretionary bonuses and/or commission. Commission payments are monthly.]

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 participates in E-Verify. To learn more, click here.

A notice to Headway applicants: To protect yourself against phishing and recruitment fraud, please note that Headway only accepts applications through our official careers page at https://headway.co/careers. Headway will never refer you to external websites, ask for payment or personal information, or conduct interviews via messaging apps. All official communication will come from a @findheadway.com email address. If you are contacted by someone claiming to be from Headway via an unofficial channel, please do not share any information and report it as spam.

1 in 4 people in the US have a treatable mental health condition, but most providers don't accept insurance, making therapy too expensive for most people. Headway’s mission is to fix this by building a new mental healthcare system everyone can access. We started by solving the biggest barrier to care: insurance. The admin work - credentialing, claims, payment reconciliation - is a nightmare. We've automated that.

But we're going further. Over 75,000 providers across all 50 states run their practice on our software, serving over 1 million patients. We are building the best tools for therapists to run their entire practice, reimagining the experience of finding a therapist, and investing in the platform foundations to enable this at scale. We aren't just a billing layer; we are becoming the platform where care actually happens.

We're a Series D company with $325M+ in funding (a16z, Accel, Spark Capital, etc.), looking for exceptional people to help us achieve this mission. We want your time here to be the most meaningful experience of your career. Join us, and help change mental healthcare for the better.

Workforce Management keeps every patient and provider who contacts Headway answered on time — at a cost that falls as we scale. We forecast demand, schedule the people to meet it, and manage the day in real time across Headway's internal team and our BPO partners — with a growing agent support operation. We run it as a lean, senior, AI-empowered team: the mechanical work goes to the machine; judgment, exceptions, and relationships stay human.

You'll be Headway's first dedicated scheduler — the owner of a function responsible for building, optimizing, and publishing schedules that keep our contact center staffed to demand, govern rosters across the network. This critical work makes our staffing spend defensible and helps make sure we scale the workforce efficiently. You'll report to the WFM Manager and partner daily with our Real-Time and Capacity Planning leads.

You Will

• Build and publish agent schedules against demand in Verint on an 8-week horizon — absorbing training classes, PTO, and overtime

• Balance rigorous SLA targets with agent well-being — design sustainable shift templates that reduce burnout and help us retain top talent

• Own network-wide roster and headcount data across Headway's internal (Core) and CX teams, including complex, high-variability shift patterns

• Reconcile scheduled hours against invoiced/productive BPO hours — the control that keeps staffing spend accountable

• Handle exceptions (time-off, swaps, coverage gaps) and partner with Real-Time on intraday adjustments and adherence

• Drive scheduling-optimization strategy through quarterly project cycles; set policy and standardize templates so the function scales with new sites and lines of business

• Adopt, test, and help shape AI-assisted scheduling — acting as the human-in-the-loop who governs automated drafts, which frees you to focus on higher-level optimization strategy

You'd be a great fit if…

• You have 3+ years in contact-center workforce management with direct ownership of scheduling

• You've worked hands-on in an enterprise WFM platform (Verint strongly preferred; NICE IEX / Aspect / Playvox welcome)

• You're fluent in staffing math — occupancy, shrinkage, coverage — and comfortable defending a number with data

• You've built complex, multi-shift rosters that held SLA, ideally in a multi-vendor or BPO environment

• You're a translator — the bridge between WFM and Operations — who can communicate the "why" behind the scheduling math and trade-offs to agents and senior leaders alike (you operate independently and set policy)

• You're excited to build a function from scratch and to work alongside AI tooling rather than around it

Compensation and Benefits:

The expected base pay range for this position is $99,280 - $146,000 based on a variety of factors including qualifications, experience, and geographic location. In addition to base salary, this role may be eligible for an equity grant, depending on the position and level.

We are committed to offering a comprehensive and competitive total rewards package, including robust health and wellness benefits, retirement savings, and meaningful ownership opportunities through equity. Compensation decisions are made holistically, ensuring fairness and alignment with market benchmarks while recognizing individual contributions and potential.

• 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

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 participates in E-Verify. To learn more, click here.

A notice to Headway applicants: To protect yourself against phishing and recruitment fraud, please note that Headway only accepts applications through our official careers page at https://headway.co/careers. Headway will never refer you to external websites, ask for payment or personal information, or conduct interviews via messaging apps. All official communication will come from a @findheadway.com email address. If you are contacted by someone claiming to be from Headway via an unofficial channel, please do not share any information and report it as spam.

1 in 4 people in the US have a treatable mental health condition, but most providers don't accept insurance, making therapy too expensive for most people. Headway’s mission is to fix this by building a new mental healthcare system everyone can access. We started by solving the biggest barrier to care: insurance. The admin work - credentialing, claims, payment reconciliation - is a nightmare. We've automated that.

But we're going further. Over 75,000 providers across all 50 states run their practice on our software, serving over 1 million patients. We are building the best tools for therapists to run their entire practice, reimagining the experience of finding a therapist, and investing in the platform foundations to enable this at scale. We aren't just a billing layer; we are becoming the platform where care actually happens.

We're a Series D company with $325M+ in funding (a16z, Accel, Spark Capital, etc.), looking for exceptional people to help us achieve this mission. We want your time here to be the most meaningful experience of your career. Join us, and help change mental healthcare for the better.

Providers run their entire practice on Headway and the tools they use every day shape both the quality of care patients receive and providers' ability to sustainably run their practice. Some of the biggest administrative burdens in a provider's week comes from managing their calendar, staying on top of messages, and coordinating scheduling with their clients.

As a Senior Designer leading our new Client Management pod, you'll own the design of Headway's calendar, scheduling, and messaging experiences. These are the surfaces thousands of providers touch every day. You'll bring systems-minded craft to complex, state-heavy problems (availability, booking and reschedule, timezones, notifications, provider–patient messaging) and keep it all coherent with how providers manage their clients. Your work helps providers spend less time on logistics and more time on care, and keeps availability accurate so patients can book.

Our design team works AI-first. Designers use Claude Code and Cursor to prototype, ideate, and ship improvements to our codebase. We want designers who already work this way and treat AI as a primary part of their practice.

• Calendar & scheduling. Availability, booking and reschedule flows, Google Calendar OAuth, and getting the hard states right (timezones, conflicts, edge cases).

• Messaging. Provider–patient messaging, attachments, and the notification/reminder system around it.

• EHR-craft papercuts. Systematically identify and fix the highest-value usability issues providers have flagged across these surfaces.

• Coherence with client management. Keep scheduling and messaging consistent with how providers manage their client list and profiles, in partnership with Product.

• Research & craft. Talk to providers with the research team's support; raise the craft bar and contribute scheduling/messaging patterns to the Helix design system.

• Have 5+ years of product design experience, with real time spent on complex, workflow-heavy product surfaces.

• Bring exceptional visual and interaction craft. You sweat the edge cases and states that make workflow surfaces trustworthy.

• Are a systems thinker who can take a messy, multi-state problem and shape it into a coherent experience.

• Are data-informed: you use qualitative and quantitative insight together to drive decisions.

• Are a strong cross-functional partner who builds alignment and drives momentum with PM, Eng, and Data.

• Prototype and test ideas quickly with Claude Code, Cursor, or your AI tool of choice. AI generates the pixels and prototype. You define the patterns, behaviors, and quality bar.

• Want your work to make a meaningful difference — these surfaces shape how providers run their practice and how reliably patients get care.

Compensation & Benefits:

The expected base pay range for this position is $180,000 - $225,000, based on a variety of factors including qualifications, experience, and geographic location. In addition to base salary, this role may be eligible for an equity grant, depending on the position and level.

We are committed to offering a comprehensive and competitive total rewards package, including robust health and wellness benefits, retirement savings, and meaningful ownership opportunities through equity. Compensation decisions are made holistically, ensuring fairness and alignment with market benchmarks while recognizing individual contributions and potential.

• 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

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 participates in E-Verify. To learn more, click here.

A notice to Headway applicants: To protect yourself against phishing and recruitment fraud, please note that Headway only accepts applications through our official careers page at https://headway.co/careers. Headway will never refer you to external websites, ask for payment or personal information, or conduct interviews via messaging apps. All official communication will come from a @findheadway.com email address. If you are contacted by someone claiming to be from Headway via an unofficial channel, please do not share any information and report it as spam.

1 in 4 people in the US have a treatable mental health condition, but most providers don't accept insurance, making therapy too expensive for most people. Headway’s mission is to fix this by building a new mental healthcare system everyone can access. We started by solving the biggest barrier to care: insurance. The admin work - credentialing, claims, payment reconciliation - is a nightmare. We've automated that.

But we're going further. Over 75,000 providers across all 50 states run their practice on our software, serving over 1 million patients. We are building the best tools for therapists to run their entire practice, reimagining the experience of finding a therapist, and investing in the platform foundations to enable this at scale. We aren't just a billing layer; we are becoming the platform where care actually happens.

We're a Series D company with $325M+ in funding (a16z, Accel, Spark Capital, etc.), looking for exceptional people to help us achieve this mission. 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 Engineering at Headway

Building a new mental healthcare system at Headway is only possible because of the scale and leverage that software can provide. Principles that guide us:

The Role

Every appointment on Headway has a financial story: what the patient owes, what the provider is paid, what the payer is billed, and whether all three ever line up. At 1.5M+ appointments a month, up from 5.6M appointments in all of 2023 to 14.5M in 2025, that story has to be told correctly, automatically, and the same way every time.

Revenue Engine is the group that owns it. We're the systems of record and the systems of movement for Headway's money: the billing platform that decides and commits what everyone owes, and the claims platform that exchanges that truth with every payer we work with. When we're right, providers get paid on time, patients get bills they can trust, and Headway can close its books quickly. When we're not, a person has to figure out why; today, more often than we'd like, that's exactly what happens.

Our work is to take systems that are largely right and making them provably right. Explainable after the fact, resilient to the failure of any one component, and correct by construction rather than by human review. It's also work where "correct" is genuinely hard to define. Payers are fickle counterparties: they respond inconsistently, silently, partially, late, or in ways that contradict what they told us last month. Some of the most interesting engineering in this group is deciding what a system should believe when the outside world won't give it a straight answer, and making that belief auditable.

We're hiring two Engineering Managers into Revenue Engine. Both roles lead a team end-to-end, and report to a leader who will give you the autonomy to run it while being a close thought partner. We're a technical engineering org: managers here lead through credibility in design reviews, not through distance from the work.

The two teams

Claims Platform

Claims Platform owns the round-trip between Headway and the payer / clearinghouse ecosystem. Outbound: reliably transmitting claims. Inbound: interpreting whatever comes back: 835 remittances, 277 claim statuses, RARC/CARC codes, rejections, and the long tail of payer responses that don't fit any of those neatly. And in between: recording the result faithfully, so that billing, collections, and the provider and patient experience all operate against the same source of truth.

Why it's interesting: durable workflow orchestration on infrastructure that moves real money, a clean financial-integrity domain, real-time payer-response processing, and a north-star metric: what fraction of appointments get a clear, conclusive payer response with a direct line to company margin.

Billing Infrastructure

Billing Infrastructure owns what Headway believes about an appointment's finances, and when. The billing system is a centralized platform (a suite of APIs) that acts as the conductor for Headway's financial outcomes, modeled after a real-world medical biller. It doesn't own how each responsibility is calculated; it owns orchestrating the specialists that do, in the right order, and committing the result. Two functions: compute (orchestrate patient responsibility, payer responsibility, and provider payout across the teams that own each input) and commit (write those results, and the inputs behind them, as immutable snapshots so any financial commitment is fully explainable after the fact).

Why it's interesting: designing the state machine that decides which financial actions an appointment is eligible for and in what order; guardrail APIs that can refuse a write the domain doesn't allow yet; immutable snapshots of every input and output, so a commitment made months ago can be reconstructed and explained exactly; a shadow mode that lets other teams simulate pricing and billing logic (and compare ML models) against real data without ever committing a financial outcome; and the non-happy paths that make it real, where a refiling, a fee-schedule change, or a correction has to reopen settled state and re-settle it safely.

What you'll own

• An engineering team: hiring to a high bar, growing the people on it, and setting the culture your team operates by.

• A core surface of Headway's financial systems: a platform other teams depend on, and a roadmap you co-own with your product partner.

• Technical direction: architecture, build-vs-buy trade-offs, reliability targets, data-model decisions, and the standard the team operates to.

• Correctness and operability: the metrics that define "right" for your domain, the observability to prove it, incident response and on-call, and the steady conversion of manual toil into automation.

• Cross-functional partnership: with the other Revenue Engine teams, with the platform teams whose inputs and outputs you depend on (benefits, payments, payouts, corrections, claims operations), and with Finance and Accounting, who consume your systems' output as the company's financial record.

Who you are

We're looking for engineering team leaders and people managers who are product-minded, data-informed, and drawn to systems where correctness is the product. As an Engineering Manager in Revenue Engine, you'll work closely with Engineering Leadership, Product, Data, Operations, and Finance to shape how Headway records and moves money. This is an exciting opportunity for a passionate, mission-aligned engineering leader to make an immediate impact at a high-growth company.

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

• You have 3+ years of experience as an Engineering Manager, building and leading teams that delivered business outcomes through technical investment.

• You have 3–5+ years of experience as a Software Engineer, with depth in backend and distributed systems: event-driven architectures, workflow orchestration, or high-reliability data pipelines.

• You've led work where correctness and data integrity were non-negotiable (financial systems, payments, billing, claims, or a similarly consequential domain), including migrations you had to de-risk rather than simply schedule.

• You're comfortable defining "correct" in an ambiguous domain: setting the metric, instrumenting it, and defending it as inputs, counterparties, and volume change underneath you.

• You have strong prioritization and roadmap judgment, and you can sequence work for a small team against a clear metric while managing real dependencies on other teams.

• You're technical enough to be a credible thought partner in a design review, and you'd rather be close to the architecture of a money-movement system than removed from it.

• You've built durable partnerships with non-engineering stakeholders (operations, finance, or compliance) whose work depends on what your systems produce.

Nice to have: healthcare claims, EDI or clearinghouse experience; fintech or payments background; experience standing up observability and SLAs on a system that didn't have them; experience growing a small team into a larger one.

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 team and people leadership experiences.

• Final rounds: You'll meet team members across product and engineering leadership for multiple behavioral interviews and two technical interviews (System Design & AI Coding), 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:

The expected base pay range for this position is $222,800 - 278,500, based on a variety of factors including qualifications, experience, and geographic location. In addition to base salary, this role may be eligible for an equity grant, depending on the position and level.

We are committed to offering a comprehensive and competitive total rewards package, including robust health and wellness benefits, retirement savings, and meaningful ownership opportunities through equity. Compensation decisions are made holistically, ensuring fairness and alignment with market benchmarks while recognizing individual contributions and potential.

• 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

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 participates in E-Verify. To learn more, click here.

A notice to Headway applicants: To protect yourself against phishing and recruitment fraud, please note that Headway only accepts applications through our official careers page at https://headway.co/careers. Headway will never refer you to external websites, ask for payment or personal information, or conduct interviews via messaging apps. All official communication will come from a @findheadway.com email address. If you are contacted by someone claiming to be from Headway via an unofficial channel, please do not share any information and report it as spam.

1 in 4 people in the US have a treatable mental health condition, but most providers don't accept insurance, making therapy too expensive for most people. Headway’s mission is to fix this by building a new mental healthcare system everyone can access. We started by solving the biggest barrier to care: insurance. The admin work - credentialing, claims, payment reconciliation - is a nightmare. We've automated that.

But we're going further. Over 75,000 providers across all 50 states run their practice on our software, serving over 1 million patients. We are building the best tools for therapists to run their entire practice, reimagining the experience of finding a therapist, and investing in the platform foundations to enable this at scale. We aren't just a billing layer; we are becoming the platform where care actually happens.

We're a Series D company with $325M+ in funding (a16z, Accel, Spark Capital, etc.), looking for exceptional people to help us achieve this mission. We want your time here to be the most meaningful experience of your career. Join us, and help change mental healthcare for the better.

Most providers don't get their patients from Headway. They get them from their own website, from Psychology Today, from word of mouth, from a colleague's referral and then they bring them to Headway. These provider-sourced patients are roughly 70% of all new patients on the platform.

Today, we have limited support for providers to manage their prospects. A provider adds a client, and from there the experience is largely passive, with little visibility into where someone is stuck, or what to do next. This role will lead the design of the provider CRM: turning the client list from a static intake form into a living prospect pipeline, and building the AI layer on top of it: a front desk and scheduling assistant that answers inquiries, books appointments, and follows up, so a solo therapist gets the operational leverage of a practice manager that they don't have to hire.

Our design team works AI-first. Designers use Claude Code and Cursor to prototype and stay involved through launch and iteration, directly in code. We want designers who already work this way and treat AI as a primary part of their practice.

• Own the provider CRM experience from the moment a prospect reaches a provider through to an active patient in care. You'll be the design anchor for the Provider Sourced Patients pod, partnering with PM and Eng on one of the largest growth levers at the company.

• Design the client list as a prospect pipeline, including stages, status, drop-off signals, and the actions a provider takes at each step. This surface barely exists today; the first job is defining what it should be, not polishing what's there.

• Design an AI front desk and scheduling assistant that handles inquiries, booking, and follow-up on a provider's behalf. You'll define new interaction patterns, trust signals, and automation boundaries, including how the system behaves when it's uncertain or wrong, with a real patient on the other end.

• Design for genuinely different providers: practice starters and veterans, therapists and prescribers, solo practitioners and group practices, each with different prospect behavior, without fragmenting the experience.

• Prototype with Claude Code, Cursor, or your AI tool of choice, and stay involved through launch. You set the standard for AI-native practice on the design team.

• Conduct research and talk directly to providers to validate solutions, with the research team's support. Understand where prospects actually come from, why they don't convert, and where automation helps vs. hinders.

• Contribute to the design system and culture, share your AI practice, prompts, and patterns with the design team.

You'll Be A Great Fit If You:

• Have 8+ years of product design experience, with significant time spent on CRM, pipeline, operational, or marketplace product work.

• Have done real 0→1 work where you've defined a product surface rather than only improving an existing one, and you're comfortable when the requirements aren't written yet.

• Think in funnels: you know how to diagnose drop-off, and you get excited when a design change moves a metric.

• Are a systems thinker who can hold a stateful, multi-actor experience in your head and the scheduling and eligibility machinery behind them, designing with awareness of the full pipeline.

• Have experience designing agentic or AI-powered workflows: conversational flows, intelligent automation, or replacing manual processes with AI-driven experiences.

• Bring strong visual and interaction design craft. You care deeply about the details and can produce polished, high-quality work at speed.

• Want your work to make a meaningful difference in people's lives. This role directly shapes how many people looking for a therapist actually make it into care.

Compensation & Benefits:

The expected base pay range for this position is $212,000 - $265,000, based on a variety of factors including qualifications, experience, and geographic location. In addition to base salary, this role may be eligible for an equity grant, depending on the position and level.

We are committed to offering a comprehensive and competitive total rewards package, including robust health and wellness benefits, retirement savings, and meaningful ownership opportunities through equity. Compensation decisions are made holistically, ensuring fairness and alignment with market benchmarks while recognizing individual contributions and potential.

• 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

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 participates in E-Verify. To learn more, click here.

A notice to Headway applicants: To protect yourself against phishing and recruitment fraud, please note that Headway only accepts applications through our official careers page at https://headway.co/careers. Headway will never refer you to external websites, ask for payment or personal information, or conduct interviews via messaging apps. All official communication will come from a @findheadway.com email address. If you are contacted by someone claiming to be from Headway via an unofficial channel, please do not share any information and report it as spam.