Headway

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 the role: You will be the first dedicated PM for pricing at Headway. Your mission: build pricing into a durable, experimentation-driven lever for growth and revenue. Success looks like creating $100M+ of revenue impact. Headway's pricing decisions affect every participant in our marketplace — what providers earn, what patients pay, and what payers reimburse. Today, these decisions are made through a mix of analysis, intuition, and competitive benchmarks. You'll replace that with a systematic, experiment-driven approach that generates data, builds conviction, and creates new revenue streams through bundling/un-bundling. This is not a strategy-deck role. You will design experiments, partner with data scientists, navigate cross-functional complexity, and ship pricing changes that move the business. You'll work at the intersection of product, economics, and marketplace dynamics in one of the fastest-growing healthcare companies in the country. You Will - Own pricing experimentation end-to-end: Design, run, and analyze pricing experiments (payout levels, take rates, fee structures, incentive models) with proper controls and measurement. - Price and package existing features: Identify opportunities to unbundle, tier, or price Headway's existing feature set as new revenue lines, while balancing the provider experience. - Define Headway's pricing philosophy: Build a principled, defensible approach to how we set prices — transparent to providers, competitive in the market, and sustainable for the business. - Inform tiering with pricing data: Partner with other product teams to ensure pricing and tier design are grounded in experimental evidence, willingness-to-pay research, and elasticity data. - Build the experimentation infrastructure: Work with Engineering and Data to create systems that enable rapid, controlled pricing experiments across geographies and segments. - Navigate cross-functional complexity: Align Finance, Provider Growth, Payer, Ops, and Legal around pricing decisions that affect every part of the business. Who You Are - 8+ years of PM experience, with at least 2-3 years owning pricing, monetization, or marketplace economics. - You've personally owned pricing or packaging strategy and shipped changes that moved revenue. - You've designed and run pricing experiments at scale — you know the difference between a feature A/B test and a pricing experiment. - Strong quantitative fluency — you can partner with data scientists on experiment design and causal inference as a peer. - You thrive in ambiguity and can build structure where none exists — this is a new team. - Bonus: SaaS pricing & packaging experience (PLG, tiering, bundling). - Bonus: You've worked in a two-sided marketplace or platform where pricing affects both supply and demand. - Bonus: Healthcare or regulated industry experience. 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 #LI-EM1 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. Headway is hiring an experienced a Senior Technical Recruiter to help build the engineering teams that will power our next stage of growth. You’ll partner closely with Engineering leaders to run high-impact searches, shape hiring strategy, and ensure an exceptional candidate experience from first touch to close. As a senior member of the recruiting team, you’ll operate as a talent advisor, diagnosing search challenges, designing sourcing strategies, influencing stakeholder decisions, and driving predictable hiring outcomes in a high-growth environment with a high talent bar. Your work will directly shape Headway’s ability to deliver for providers and patients nationwide. You will: - Run full-cycle searches across the engineering org, driving everything from intake to offer while partnering closely with sourcers, coordinators, and hiring teams - Act as a strategic partner to hiring managers, advising on role definition, search strategy, market realities, and funnel expectations - Use data to diagnose and improve search, quickly refining the approach and/or process as needed to accelerate progress - Build Olympic-level pipelines through targeted sourcing strategies - Ensure every search follows a structured, inclusive process that raises the hiring bar and improves consistency across teams - Deliver an exceptional candidate experience through every step of the process You’d be a great fit if… - Bring 5+ years of full-cycle recruiting experience in high-growth, tech-enabled environments (in-house or blended agency) - Have deep experience hiring engineering roles - Operate as a business partner, using market insights and data to guide hiring managers toward better, faster decisions - Break down complex searches into clear plans, diagnosing bottlenecks and proposing solutions proactively - Manage multiple searches with structure, balancing high volume with attention to detail and predictable execution - Think creatively about sourcing to find and engage top technical talent - Care about operational excellence with a focus on constantly improving your workflow and reducing friction for candidates and stakeholders - Communicate clearly and with presence, whether aligning with hiring managers or guiding candidates through the process 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. As a Provider Growth Associate (Account Executive), you’ll have an instrumental impact as we expand Headway across the country. You’ll be directly responsible for scaling our community of therapists and psychiatrists in order to increase access to quality care for those who need it. As a sales expert in a rapidly scaling environment, you’ll be on the front line of expanding our therapist networks through a full-cycle sales motion. As the first point of contact for prospective providers, you’ll work cross-functionally to translate the insights you glean from your sales process into products and processes that help us execute on our mission. You'd love this role if: - You have 1-3 years experience in consultative sales or consumer sales (bonus points if you’ve done this in a startup environment, or sold to small businesses before) - You know how to connect with people whether in person, over the phone, or over email - You have a deep work ethic and the desire to continuously improve - You like to be challenged and push yourself to get better every day and in every pitch - You have thick skin, and are comfortable thinking on your feet, trying new approaches, and bouncing back when things don’t go your way - You take a scientific approach to growth, experimenting with a variety of tactics to discover how to generate leads and sell you have the analytical ability to identify which channels warrant more investment, and which we should avoid - You want to learn and grow. You view this role as an opportunity to learn from a bright and talented team and are excited to take on more responsibility at Headway over time - You believe in our mission - You want to work for Headway because you believe in the importance of affordable and accessible mental health care, for everyone Compensation and Benefits: - Salary information is based on a single salary target per role and is differentiated based on geographic location. - Group A = $77,000 - New York City, San Francisco/Bay Area, Los Angeles / Orange County Area, San Diego, Seattle, Boston, Austin - Group B = $69,300 - Chicago, Denver, Washington DC, Philadelphia, Pittsburgh, Atlanta, Nashville, Phoenix, and Portland - Other compensation includes commission. Commission payments are monthly. - 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. Headway is seeking a Senior Revenue Manager to help shape the revenue accounting strategy in close partnership with the Director of Revenue Accounting and own its execution through a best-in-class operating model. You will own the day-to-day execution of revenue accounting, lead and develop a team of Senior Revenue Accountants, and drive continuous improvements across processes, systems, and controls. This is a highly cross-functional role partnering with Finance, Legal, Data, Engineering, Product, and Operations on revenue-impacting initiatives. This role offers the opportunity to have a meaningful impact on how revenue is accounted for, reported, and scaled at Headway. You will: - Own the operational execution of the revenue accounting function, ensuring accurate, timely, and compliant revenue reporting under ASC 606 - Lead and develop a team of Senior Revenue Accountants, setting clear expectations, coaching for growth, and building a high-performance culture - Drive the revenue month-end close process, ensuring consistent, timely delivery and continuous improvement in close quality and efficiency - Serve as a key thought partner to the Director of Revenue Accounting, providing operational insights, risk assessments, and recommendations to help shape the revenue accounting strategy - Elevate issues, patterns, and opportunities observed in execution into clear, actionable input that informs strategic decisions for the revenue accounting function - Partner cross-functionally on revenue-impacting initiatives, serving as a key operational lead to drive alignment and effective delivery - Oversee the design, implementation, and maintenance of scalable revenue processes, policies, and internal controls - Drive the adoption of AI and automation across revenue accounting processes to improve scalability, accuracy, and efficiency - Play a key role in audit readiness and execution for revenue, including reviewing support, resolving issues, and strengthening documentation You’d be a great fit for this role if: - You have 8+ years of accounting experience, including significant experience in revenue accounting at high-growth companies - You have 5+ years of experience managing or leading others,including experience leading senior individual contributors and/or other managers, with a demonstrated ability to develop talent and drive results through teams - Strong working knowledge of ASC 606, with hands-on experience applying revenue guidance in practice - You have experience operating in fast-paced, cross-functional environments with evolving systems and processes - You are both highly detail-oriented and comfortable operating at a higher level, connecting execution to business outcomes - You are an excellent communicator who can translate complex accounting topics for non-accounting partners - You bring a builder mindset and enjoy creating structure, clarity, and scalable solutions - You are a CPA with Big 4 and/or high-growth company experience Compensation and Benefits: The expected base pay range for this position is $130,560 - $204,000, 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 #LI-LN1 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 This RoleWe're looking for Staff PMs who are curious about what AI makes possible and eager to build in an environment where it's a core part of the toolkit — not a side project. We are hiring across Patient, Provider, Payer, and Platform. The right candidates will bring strong product fundamentals and a willingness to build with AI in a regulated, high-stakes industry. Staff PMs at Headway own product areas end-to-end: setting strategy, partnering deeply with engineering, data science, and design, and driving outcomes that move the company. AI is changing how we build at Headway, and the size of opportunity for Headway to leverage AI is massive. We sit at the intersection of healthcare delivery, complex insurance systems, and a multi-sided marketplace serving tens of thousands of providers and millions of patients. AI is increasingly part of how we solve these problems — and we want PMs who are energized by that, whether they're deep in AI already or strong product thinkers ready to learn. The Problems We're SolvingFor PatientsFinding the right therapist, understanding your insurance benefits, and staying in care shouldn't be hard. Today it is. We're building AI-powered matching and personalized care navigation that help patients get into — and stay in — mental health care at scale. One million patients a month ask for a referral to a mental health provider. We're building the systems that ensure they actually get there. For ProvidersTherapists spend a staggering amount of time on administrative tasks — credentialing, documentation, scheduling, billing — instead of with their patients. We're using AI to automate clinical workflows, simplify complex insurance requirements, and give providers more time to do what they came here to do. The goal: a thriving practice on Headway that practically runs itself. For PayersHealth insurers are asking harder questions: Is care on Headway actually working? Is it worth what we're paying? We're using AI to answer them at scale — measuring clinical outcomes, building dashboards that demonstrate responsible care, and moving toward a model where patients are matched to the right care pathways and providers are aligned around better outcomes. This work protects Headway's standing with insurers and opens doors to deeper, more strategic partnerships. For PlatformThe infrastructure underneath Headway — billing, claims, payments, and trust and safety — needs to scale reliably at the speed of our growth. We’re using AI to automate complex, high-volume workflows, detect fraud and errors faster, and build systems that get smarter over time. This is foundational infrastructure with direct impact on Headway's economics and compliance posture. What You'll Do at Headway - Define and own the product strategy for your area in partnership with engineering, design, data, clinical, and operations teams - Apply AI where it matters: identify where intelligence creates step-change improvements in your product area and drive those bets from insight through production - Set and own clear success metrics; communicate results and course-correct with urgency - Represent the voice of your customer — patient, provider, or health plan — with conviction in every decision, grounded in data and direct research You'd Be a Great Fit If… - You have 8+ years of product management experience with a track record of owning complex, high-impact product areas - You have experience with LLM systems — prompting, retrieval, evaluation, fine-tuning — and a track record of shipping AI-powered products that hold up at scale, not demos. - You've built at scale in a marketplace, platform, or data-intensive environment — and can show the outcomes you drove - You're energized by working in regulated, complex industries and see constraints as a product design challenge rather than a blocker - You can influence across engineering, clinical, legal, finance, and operations — and you're equally comfortable in the data and in the room - You have strong quantitative fluency and can partner with data scientists on experiment design and causal analysis - You communicate with precision — in writing, in product reviews, and with senior leadership Compensation and 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 #LI-EM1 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 the Role As Headway deepens its partnership with one of our most strategic national health plans, we're looking for an Associate Principal, Payer Partnerships to own the commercial relationships and channel strategy that will expand our footprint and make Headway the go-to mental health partner across the plan's book of business. Reporting to our Principal, Payer Partnerships, you'll work at the intersection of payer commercial teams, building the trust and advocacy that turn a strong partnership into a dominant one. You will: - Develop and strengthen senior-level relationships with commercial leadership at our health plan partner, ensuring Headway is known, trusted, and actively championed across their organization - Develop Headway's understanding of patient acquisition channels, forming a point of view on which segments have appetite for deeper Headway engagement, which partners can facilitate that, and what the strategic tradeoffs are - Collaborate with internal, cross functional stakeholders to deliver insights to inform product and operations strategy - Drive strategic initiatives that deepen the partnership, identifying where Headway can expand its role, generate new demand, and increase stickiness across the plan's commercial ecosystem - Build in a way that scales: document your approach so the commercial channel playbook you develop can be replicated across other accounts You'd be a great fit if... - You have a minimum of 7+ years of experience in the healthcare space, preferably in roles within Business Development, or in Strategic Partnerships/Customer-facing roles - You have a track record of building meaningful relationships from scratch in complex, matrixed organizations — and you do it strategically, not just by being personable - You've worked in or closely adjacent to the commercial side of healthcare, like at a digital health company with payer or employer channel exposure - You don't wait for clarity to come to you; when the path forward is unclear, you identify the right questions, find the people and data that can answer them, and form a point of view before anyone asks you to - You are operationally excellent, able to manage multiple high impact customers and large volume of moving pieces without breaking a sweat - You think in playbooks. You don't just execute; you document your logic so others can build on it Compensation and Benefits: The expected base pay range for this position is $130,000-$200,000, 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 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. As a Strategic Finance Lead, GTM, you will sit within the Strategic Finance team and play a critical role in ensuring capital is deployed efficiently across Provider and Patient Growth initiatives. This is a highly cross-functional role for someone who thrives at the intersection of financial analysis and strategic decision-making. You'll build models, track performance, and surface insights that guide how we allocate resources and scale our GTM investments. You Will - Build and maintain financial models to assess GTM investment efficiency, scenario plan, and evaluate trade-offs across growth initiatives - Own budgeting and forecasting processes for GTM spend, partnering with budget owners to align plans with strategic priorities. - Analyze operating KPIs and funnel data to evaluate unit economics, channel performance, and overall GTM effectiveness - Partner cross-functionally to surface insights and support strategic decision-making - Develop dashboards, reporting, and executive-ready materials to communicate progress against goals You’d be a great fit if… - You have 4+ years of professional experience, ideally in a mix of financial services (Consulting / Equity Research / Private Equity) and highly analytical roles at a fast-growing company (Strategic Finance) - You are highly proficient in Google Sheets (advanced formulas) and Looker (or similar BI tools) and comfortable working with large datasets - You are detail-oriented and have a “measure twice, cut once” approach when working with financial data - You’re excited to work cross functionally with the business teams to develop a greater understanding of function-specific efficiency metrics and help course-correct where necessary - You take ownership and are a resourceful self-starter—you proactively seek context, solve ambiguous problems, and anticipate stakeholder needs - You are excited about AI and how it's reshaping finance, and you actively explore and apply AI tools to drive faster insights, greater efficiency, and smarter decision-making - You communicate complex insights clearly, tailoring your message for different audiences (finance vs. marketing) - You thrive in a fast-paced, cross-functional environment and enjoy collaborating with marketing, finance, and growth teams - You are excited about joining a mission-driven company and driving marketing efficiency to improve mental healthcare access Compensation and Benefits: The expected base pay range for this position is $131,750 - $165,000, 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 #LI-LN1 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. As Senior Counsel, Regulatory, you will be a key strategic partner responsible for partnering with Product, Engineering, Operations, and Privacy teams to support innovation during a pivotal growth phase. This is a unique opportunity to join a mission-driven healthcare technology company where legal is viewed as a strategic partner rather than a roadblock. You will serve as the primary regulatory attorney and thought partner for Headway's Clinical and Operations teams, with particular focus on health laws and regulations that impact patient care and related build of innovative technology products. While we prefer candidates based in New York, we will consider exceptional candidates nationwide. - Serve as embedded regulatory thought partner to Clinical and Operations teams, providing real-time guidance on clinical practice, telehealth modalities, PC operations, and clinical regulatory implications for product development - Partner with Clinical and Compliance team on policy development, audit response, and remediation strategies while providing legal interpretation of healthcare regulations - Translate complex healthcare regulations into practical guidance and tools that Clinical and Operations teams can easily understand and implement - Anticipate regulatory challenges and proactively develop solutions that enable business objectives while facilitating compliance - Build strong relationships across teams to position regulatory guidance as a business enabler rather than an obstacle You would be a great fit if you have: - 5+ years of post-bar admittance legal experience with significant healthcare regulatory expertise, particularly in health technology, corporate practice of medicine, behavioral health clinical practice, and CPOM - Deep understanding of multi-state healthcare regulations (e.g. telehealth) in evolving regulatory environments - Experience serving as a trusted advisor to Clinical, Operations and/or Compliance teams in a healthcare technology environment - Proven ability to translate complex healthcare regulatory requirements into clear, actionable guidance for non-legal stakeholders - Track record of balancing compliance obligations with business objectives in fast-paced organizations - Strong communication skills and political savvy to navigate competing priorities and build effective partnerships - JD from accredited law school and active bar membership in good standing (ability to register as NY in-house counsel required) Compensation and Benefits: The expected base pay range for this position is $179,200 - $280,000, 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.

Role Description Headway is looking for an experienced QA Lead to evolve how quality works across our CX organization as we move from manual evaluation to a system that generates insights continuously, surfaces behavioral trends at scale, and drives the decisions that make our agents better and our customers better served. This is a customer support quality assurance role focused on agent evaluation, conversation analytics, and AI-powered quality measurement — not software testing, test automation, or CI/CD engineering. You'll be joining the Agent Success team within Customer Experience, a function focused on making our CX agents more effective, more consistent, and better supported. QA is in active evolution here; we're moving from a manual, sampling-based model to a specialized, insight-driven system, and the people we hire will have a direct hand in building it. Your role will have real ownership over a defined area of the QA program — calibration and framework governance, AI-powered analytics and insights, or vendor and partner quality oversight, depending on role fit. This isn't a traditional QA role where you spend your days manually grading interactions. You'll design the systems, analyze the signals, and surface the patterns that change how we operate, with clear ownership over outcomes. Your work will give CX leadership consistent, reliable visibility into performance, process, and operations — and the context to act on what they find. - Own a defined area of the QA program end-to-end (calibration and rubric governance, AI-powered analytics, or partner quality) and drive it from signal to action. - Set quality standards and rubric logic for your area; ensure consistent application across channels and partners and recommend framework updates based on outcomes. - Configure and continuously improve AI-QA tooling (ObserveAI or similar) with set scoring logic, monitoring accuracy, and ensuring the platform delivers consistent, actionable output. - Build automation into QA workflows to reduce manual overhead and expand coverage; establish AI-assisted processes for status updates, reporting, and initiative recaps. - Analyze quality and conversation data to surface DSAT drivers, behavioral trends, escalation patterns, and workflow gaps by going beyond what happened to understand why. - Design and maintain dashboards that track key quality metrics; translate findings into clear operational recommendations for CX leadership. - Produce structured insight reports (clear signal, root cause, recommended action) and ensure findings flow into training, content, coaching, and product decisions. - Contribute QA input to WBR/MBR cycles and cross-functional planning; give leadership consistent visibility into program health and customer experience impact. - Partner with BPO teams and CX stakeholders to align on standards, drive calibration, and keep expectations consistent across every channel and partner. - Collaborate with Enablement, Knowledge, and Programs to ensure quality signals drive decisions across training, content, and coaching and deliver initiatives that measurably improve agent quality and customer satisfaction. Qualifications - 4–7 years in CX operations, QA, or analytics — you've genuinely owned a program (not just contributed to one) and have specific, measurable outcomes to point to. - Comfortable pulling and analyzing data without a dedicated analyst (Looker, Metabase, Hex, or similar; SQL is a plus). - You've worked with QA and conversation intelligence tools (ObserveAI, Rippit, Level AI, Klaus, or similar) and know how to configure, calibrate, and get meaningful output from them. - You use AI as part of how you actually work with automations, workflow improvements, faster paths to insight. - You've produced insight reports that moved real decisions, where training shifted, processes changed, policy updated. - You don't just identify problems, you design the processes that prevent them from recurring. - You can translate quality data for non-QA audiences and influence decisions without formal authority. - You are comfortable in ambiguity and move fast without sacrificing rigor, and you're fine building the playbook as you go. - You are fluent in quality evaluation methodologies, calibration processes, and QA framework design. - You have a track record coordinating across operations, training, content, and technology teams to deliver shared goals. - You are a strong communicator, demonstrated with clear status reports, insight briefs, and stakeholder presentations. - You are motivated by the mission: making mental healthcare affordable and accessible. Compensation and Benefits - The expected base pay range for this position is $95,200-$140,000, 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. - 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

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 This Role: Every month, hundreds of thousands of patients and providers interact with Headway's support systems. Today, most interactions are handled by human agents working across disconnected tools. We believe CX is a product, not just a department — and the right product leader can transform how Headway supports its customers while dramatically improving both satisfaction and cost efficiency. As Director of Product for CX, you will build Headway's CX product function from the ground up. You'll own the product vision and strategy for how patients and providers get help — from AI-powered self-resolution to context-aware agent tooling to the feedback loops that connect support insights back to the product. You will: - Define the vision and strategy for Headway's CX product — spanning AI-powered resolution, agent tooling, proactive engagement, channel strategy, knowledge systems, and the feedback loops that connect support insights back to the product. - Build and lead a team of product managers focused on reducing cost-to-serve while increasing resolution quality and customer satisfaction. - Own the AI resolution layer — build the agentic workflows and API integrations that enable the AI agent to actually resolve problems, not just answer questions. Define the autonomy framework: what AI handles without human involvement, what needs guardrails, and what requires a human. - Build proactive engagement — systems that contact customers before they discover problems. Shift Headway's CX from reactive to proactive. - Launch and unify all contact channels — email, text, and voice — with intelligent routing that delivers differentiated experiences based on customer context, value, and issue type. - Own the knowledge and quality layer — machine-readable SOPs, AI evaluation frameworks and crisis escalation pathways. - Partner deeply with CX Operations to build agent tooling that makes human agents dramatically more effective — AI copilot, full journey context, auto-generated summaries. - Close the feedback loop: build the system that identifies the highest-impact product defects driving support volume and surfaces them to insurance platform teams for upstream fixes. - Establish measurement frameworks that connect CX product investments to business outcomes.. You'd Be a Great Fit If... - You are a product leader with 8+ years of experience, including at least 3 years managing PMs, with a track record of building CX/support products at scale. - You have a strong point of view on how AI will transform customer support — and you've shipped AI-powered CX products. - You've launched or scaled multi-channel CX systems and used intelligent routing for personalized experiences. - You've demonstrated the ability to simultaneously reduce support costs and improve customer satisfaction. - You thrive at the intersection of product and operations. - Nice to have: experience in healthcare, insurance, or other industries with complex customer interactions. Compensation and Benefits: The expected base pay range for this position is $300,000 - $375,000, 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.