---
title: 'Compensation Lead at Headway'
canonical: 'https://feeny.ai/job/compensation-lead-headway-remote-31mhamv2fc3t'
type: 'job'
last_seen: '2026-11-08'
---

# Compensation Lead at Headway

- **Company:** [Headway](https://feeny.ai/companies/headway)
- **Location:** Remote
- **Employment:** full-time
- **Work type:** remote
- **Posted:** 2026-11-06
- **Last confirmed live:** 2026-11-08
- **Apply:** https://jobs.ashbyhq.com/headway/2777786a-fe3e-4e61-a1dc-5993a569af87

## Job description

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 90,000 providers across all 50 states run their practice on our software, serving over 2.6 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, and building much of it with AI. 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 the Team & Role

At Headway, our Total Rewards team helps shape how we attract, retain, and reward the olympic-level building the future of healthcare. We own the pay ranges, equity programs, and compensation cycles behind thousands of pay decisions each year. We're hiring a Compensation Lead to help build the next stage of our compensation function. This is a high-impact individual contributor role reporting to the Compensation Manager. You'll own the analysis, programs, and the systems and processes behind how Headway pays people, from market pricing and pay positioning, to offers, annual compensation cycles, and equity. You’ll excel in the “gray area”: when questions arrive without a clear method or owner, you will be able work out what's actually being decided, build the analysis that answers it, and explain it clearly to the people who have to act on it. We're building a more modern, tech-enabled way of doing compensation work, and while you'll use AI and automation every day, your strategic thinking and judgment will make the final call. You don't need to have spent your whole career in compensation, or have compensation experience at all, but you do need to be analytical, comfortable with ambiguity, and able to build partnership across People, Talent, and Finance. You’ll be strategic and business-facing, and should enjoy the hands-on, detail-heavy side of compensation work.

You Will:

- Lead the analysis behind our annual compensation cycles: pricing roles against the market, updating our ranges, modeling budget scenarios, and preparing the materials leaders need to make informed decisions
- Build the recommendations behind new hire offers, promotions, and equity actions, and dig into the cases that fall outside our guidelines with recruiters and HRBPs.
- Build the models, frameworks, and tools that keep compensation decisions consistent as we scale.
- Help run and improve our company-wide compensation processes and tighten the steps that create rework every time they come around.
- Simplify and scale how the team works, improving processes, documentation, reporting, and workflows to reduce manual effort for employees and partners.
- Use AI and automation in your day-to-day work to pull context, flag exceptions, draft decision materials, prototype solutions, and automate recurring analysis.
- Serve as a trusted compensation partner to HRBPs, Talent Acquisition, managers, and other stakeholders, bringing analytical rigor and sound judgment to their questions.
- Bring rigor to compensation data and systems, partnering across Workday, Pave, Carta, and other tools to improve data quality and catch issues before they reach a decision.

You’d Be a Great Fit If:

- You have 4+ years of experience in compensation or total rewards, consulting, finance, or a similar analytical role.
- You have strong analytical and problem-solving skills, with advanced Excel or Google Sheets skills and a track record of turning complex questions into clear recommendations.
- You have hands-on experience using AI tools to build, test, automate, and improve your own workflows, with good judgment about where AI helps and where human analysis matters most.
- You're a clear, confident communicator who can explain complex or sensitive compensation topics to non-experts, handle pushback, and build trust across functions.
- You have a high bar for accuracy and quality, particularly with sensitive compensation, equity, and performance data, and you handle it with discretion.
- You’re a self-directed problem solver with a builder mindset who is comfortable with ambiguity, enjoys creating structure, and looks for ways to improve how we work.

Comprehensive benefits: Medical, dental, vision, HSA/FSA, 401(k) including match for 2027!, Carrot Fertility reimbursement, and paid parental, medical and caregiver leave.

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.](https://www.e-verify.gov/sites/default/files/everify/posters/EVerifyParticipationPoster.pdf)

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](http://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.

## About Headway

## Company Overview
- **One-liner**: Headway is building a new mental healthcare system by creating the first software-enabled national network of therapists who accept insurance, making care affordable and accessible.
- **Entity Type**: Private (Series D)
- **Headquarters**: New York City, New York, USA
- **Founded**: 2019
- **Founders**: Not publicly listed on primary sources

## Core Business
- **Primary industry**: Mental Healthcare Technology / HealthTech
- **Target customers**: B2B (therapists and group practices) and B2C (patients seeking mental health care)
- **Mission or purpose statement**: "To build a new mental healthcare system, rewired for access and affordability." [headway.co](https://headway.co/about-us)

## Products & Services
- **Headway Platform (Provider Side)**: A software platform that enables therapists and psychiatrists to accept insurance, manage billing, and grow their private practice. It removes the administrative burden of insurance credentialing and claims, allowing providers to focus on care.
- **Headway Platform (Patient Side)**: A marketplace where patients can find and book in-network therapists and psychiatrists, with costs as low as $0/session after insurance. The platform handles scheduling, insurance verification, and billing.

## Market Standing
- **Valuation/Market Cap**: Not publicly disclosed (Series D private company)
- **Key Metric**: Over $325 million in total funding raised (Series D) [builtin.com](https://builtin.com/company/headway)
- **Notable Investors/Partners**: Andreessen Horowitz (a16z), Accel, GV (Google Ventures), Spark Capital, Thrive Capital, Forerunner Ventures, and Health Care Service Corporation. [builtin.com](https://builtin.com/company/headway)
- **Growth Signals**: 
  - Network of over 70,000 therapists and psychiatrists across all 50 states [headway.co](https://headway.co/)
  - Over 30 million sessions held [headway.co](https://headway.co/)
  - Served over 1 million patients [builtin.com](https://builtin.com/company/headway)
  - 604 U.S.-based employees (Medium-sized company) [greatplacetowork.com](https://www.greatplacetowork.com/certified-company/7083261)
  - 259 Product + Tech employees [builtin.com](https://builtin.com/company/headway)
  - Named #48 on Fortune Best Workplaces in Health Care™ 2025 (Small And Medium) [greatplacetowork.com](https://www.greatplacetowork.com/certified-company/7083261)

## Competitive Advantages
- **Asset-free network model**: Unlike competitors that build their own clinics, Headway enables existing independent therapists to accept insurance without administrative burden, creating a scalable, capital-light network.
- **Insurance integration**: Partners with 100+ of the nation's top insurance plans, making it the largest mental health provider network in the U.S. [headway.co](https://headway.co/)
- **Software moat**: The platform handles credentialing, billing, and compliance, solving the core reason 70% of therapists don't accept insurance. [headway.co](https://headway.co/about-us)
- **Scale**: With 70,000+ providers and 30M+ sessions, the network effects are significant—more providers attract more patients, and more patients attract more providers.

## Strategic Focus
- **Expanding the provider network**: Continuing to onboard therapists and psychiatrists to increase access and coverage.
- **AI and product innovation**: Actively hiring for roles like "Applied AI Lead" and "Staff Product Manager, AI Patient Experience," indicating a focus on using AI to improve patient matching, scheduling, and care delivery. [headway.co](https://headway.co/careers)
- **Deepening insurance partnerships**: Working with 100+ insurance plans to lower costs for patients and expand in-network access.
- **Scaling the patient experience**: Investing in data science, product management, and engineering to improve the patient journey from search to booking to ongoing care.

## Why Work Here
- **Culture**: 88% of employees say Headway is a great place to work, compared to 57% at a typical U.S. company. [greatplacetowork.com](https://www.greatplacetowork.com/certified-company/7083261)
- **Mission-driven**: Employees are united by the goal of building a new, accessible mental healthcare system. The company highlights that "people are their happiest, healthiest, and best selves when they know their team values them for who they are." [headway.co](https://headway.co/careers)
- **Remote-first with office hubs**: Employees work remotely across the US, with the option to work from offices in New York City, San Francisco, and Seattle. [builtin.com](https://builtin.com/company/headway)
- **Diversity & Inclusion**: The company states a commitment to building a diverse, equitable, and inclusive team, noting it is "a business imperative" and "the right thing to do." [headway.co](https://headway.co/careers)
- **Recognition**: Certified as a Great Place to Work® (88% of employees say it's a great place to work) and ranked #48 on Fortune Best Workplaces in Health Care™ 2025. [greatplacetowork.com](https://www.greatplacetowork.com/certified-company/7083261)
- **Notable perks**: Remote-first culture with optional offices in NYC, San Francisco, and Seattle; strong focus on engineering, data science, and AI roles.

## Sources
1. [headway.co - About Us](https://headway.co/about-us)
2. [headway.co - Careers](https://headway.co/careers)
3. [headway.co - Homepage](https://headway.co/)
4. [builtin.com - Headway Company Profile](https://builtin.com/company/headway)
5. [greatplacetowork.com - Headway Certification](https://www.greatplacetowork.com/certified-company/7083261)

## Other roles at Headway

- [Director, Consumer Comms & Social Media](https://feeny.ai/job/director-consumer-comms-social-media-headway-remote-mbx28gm2x2g5)
- [Office Manager](https://feeny.ai/job/office-manager-headway-san-francisco-e4aynyf2pt0p) — San Francisco, CA
- [Senior / Staff Product Manager, Patient Home Experience](https://feeny.ai/job/senior-staff-product-manager-patient-home-experience-headway-remote-syjfaqbpsm1x)
- [Senior Digital Marketing Channel Manager, SEO & AEO](https://feeny.ai/job/senior-digital-marketing-channel-manager-seo-aeo-headway-remote-6k0rxfn1cyhc)
- [Digital Marketing Channel Manager, Affiliate and Creator/Influencer](https://feeny.ai/job/digital-marketing-channel-manager-affiliate-and-creator-influencer-headway-vpv833advhg0)
- [Security Engineer (Detection & Response)](https://feeny.ai/job/security-engineer-detection-response-headway-remote-7bf1sv7rn1ph)
- [Digital Marketing Channel Manager, Social & Premium Video](https://feeny.ai/job/digital-marketing-channel-manager-social-premium-video-headway-remote-h94stejpwft6)
- [Senior Engineering Manager (Patient New Verticals)](https://feeny.ai/job/senior-engineering-manager-patient-new-verticals-headway-remote-wp3dy0bnah87)
- [Staff Data Scientist, SEO & AEO](https://feeny.ai/job/staff-data-scientist-seo-aeo-headway-new-york-drmfn0hwzyfm) — New York, NY
- [Head of Strategy & Operations, Office of the COO](https://feeny.ai/job/head-of-strategy-operations-office-of-the-coo-headway-new-york-nkdarr3ycsz8) — New York, NY