Headway

Lead go-to-market strategies and differentiated messaging to increase provider adoption and engagement, translating provider insights into product strategy and marketing plans with cross-functional teams. | Requires over 8 years of product marketing experience in consumer, marketplace, or product-led businesses, plus a track record leading complex cross-functional initiatives and influencing product strategy. | 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 Role: Headway has built the largest network of mental health providers in the country, with 85,000 active and growing. As we scale, we have an opportunity to deepen how providers understand, experience, and value Headway across their journey. Ultimately, we want to be the partner providers count on to build a thriving practice and help more patients make progress toward their goals. We're looking for a Staff Product Marketing Manager to help providers discover, adopt, and get lasting value from the products and experiences Headway builds. You'll shape how we bring new capabilities to market, build a differentiated story around the value Headway delivers, and help providers see us as a partner in building a thriving practice. This is an individual contributor role reporting to the Director of Provider Marketing. You'll partner closely with Provider Experience, Design, Lifecycle Marketing, Research, Creative, and other marketing teams to turn provider insight into strategies that drive product adoption, engagement, and retention. This is a role for someone who likes building. You Will: Build deep provider insight. Understand provider needs, behaviors, and the competitive landscape, and bring that perspective into Product decisions. Own provider positioning and messaging. Turn provider insight and product capabilities into a clear, differentiated story that helps providers understand our value and deepens trust over time. Lead Provider Experience GTM. Bring new products and capabilities to market, leading strategies that drive adoption, engagement, and retention. Lead GTM channel planning and execution. Translate GTM strategy into an integrated marketing plan and lead cross-functional marketing partners to execute against shared goals. Find the leverage. Identify the highest-impact opportunities to improve the provider experience and drive adoption and engagement, even before a brief or roadmap exists. Equip teams to tell a consistent story. Give Lifecycle, Growth, Enablement, and Customer Success the frameworks and tools they need to bring our provider story to life. You’d be a great fit if… You have significant PMM experience (8+ years) in consumer, marketplace, SMB, subscription, or product-led businesses, with a track record of bringing products to market and driving adoption. You know the customer and market cold, can build positioning and messaging, and have influenced Product strategy, not just supported launches. You understand how to drive product adoption and engagement, connecting customer insight, product value, and GTM execution to measurable business outcomes. You're comfortable with ambiguity, can form a point of view without perfect information, and know how to prioritize what matters most. You can lead complex cross-functional work across Product, Lifecycle, Customer Success, Research, and Creative without formal authority. You hold strong points of view with senior stakeholders and change them when the evidence changes. You use AI to improve your work and build workflows that improve the quality or velocity of the broader team. Compensation and Benefits The expected base pay range for this position is $190,400-$238,00 based on a variety of factors including qualifications, experience, and geographic location. 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 reimbursement and membership 13 paid holidays + company holiday break Flexible PTO 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.

You would manage BPO partner performance, coordinate between partners and internal teams, and use performance data to improve patient experience and scale operations. | The role requires 4+ years in contact center or CX operations, experience managing outsourced teams, and a record of building operational structure. | 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 Headway is looking for an experienced Vendor Operations Lead to own our patient-facing BPO partnerships and drive results. The person in this role will help scale the programs that connect people with mental health care as Headway grows. Our Customer Experience team is the tip of the spear that will make affordable mental health care a reality for millions, and you will be there to shape the experience patients have when they first reach out. In this position, you will bring a bias for action to a fast-moving, high-volume operation. You'll manage day-to-day partner performance, hold our BPO partners to clear standards, and be the main point of contact between the BPO and our internal teams. You'll work closely with partner leadership to improve conversion, so more patients who reach out leave with an appointment, while keeping quality and service strong. The person in this role will have the opportunity to build the systems, processes and structure a fast-growing program needs. You'll play a pivotal role in strengthening the foundation behind key metrics like conversion, quality, responsiveness and patient satisfaction. You Will Own day-to-day BPO partner performance, including tracking results against goals and leading improvement initiatives. Serve as the main point of contact between our BPO partners and internal teams, keeping priorities and expectations aligned. Meet regularly with BPO leadership to address ongoing challenges and keep performance moving toward goal. Use data to spot trends, find root causes, and turn insights into clear action plans. Partner with cross-functional teams to make sure BPO partners have what they need to succeed. Build and improve the processes and structure that let our programs scale. Contribute to the short, medium and long-term strategy for Headway's BPO operations. You’d be a great fit if… You've worked in contact center or CX operations for 4+ years and have a strong understanding of its metrics, processes and tools. You have experience managing BPO or outsourced teams, and you know how to build a respectful partnership while holding partners accountable for results. You're analytically minded and use data to understand why performance changed and what to do about it. You have a track record of improving operations and building structure where none existed. You're operationally excellent and unflappable in a fast-moving environment. You seek an environment that fosters growth through open feedback and high autonomy. You're motivated by the opportunity to make an impact on one of our generation's defining problems: making mental health care accessible and affordable. Bonus: you've managed BPO teams in a sales, conversion or retention capacity. This is a full-time position open to candidates across all US geographic locations. Headway employees work remotely across the US, with the option to work from our offices in New York City or San Francisco. Candidates must have a quiet, private work space equipped with high-speed internet to fulfill shifts. 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 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.

Lead an infrastructure team building scalable cloud systems, advancing self-service infrastructure, responding to incidents, and developing the platform strategically. | Requires 5–7+ years of engineering leadership and 5+ years of software or infrastructure engineering, with deep AWS expertise and platform strategy experience. | 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 Engineering at Headway Building a new mental healthcare system at Headway is only possible because of the scale and leverage that software can provide. The engineering team at Headway is a small but mighty team using technology to build that future (and have a fun time while doing it!). About this role You'll lead the Infrastructure team — one of three teams in Engineering Foundations, alongside Agentic Engineering and Eddy, Headway's internal AI platform — that every other team at Headway builds on. You'll own cloud infrastructure, deployment pipelines, LLM infrastructure (gateway, multi-provider failover, per-team rate limiting), the database platform, observability, and incident response, while hiring and growing a high-performance team shipping at AI-accelerated velocity. As AI dramatically increases code velocity across the org, our mandate is to make every change safe from the start and build systems that get safer as they get faster, working toward a model where routine infrastructure is self-serve and the team spends the majority of its time on strategic platform work. That means owning the reliability, performance, and scalability of Mamba, Headway's FastAPI/Python monolith, and the AWS infrastructure it runs on. This is a technical leadership role: you'll set strategy and vision for the team, report to the Head of Engineering Foundations, and lead through credibility in design reviews and incident response, not through distance from the work. What You'll Own An engineering team: hiring to a high bar into a growing team, developing engineers through the senior and staff levels, and running an effective on-call rotation for a team the rest of engineering depends on. The infrastructure platform: a system every other Headway team builds on, and a roadmap spanning cloud infrastructure, deployment pipelines, LLM infrastructure, the data layer, and observability. The shift from reactive to strategic: driving the team's operating model toward self-serve infrastructure, so the team spends more time on strategic platform work and less on routine support requests. Blast-radius reduction: leading the architectural and deployment validation work that contains the scope and duration of incidents when they happen. The org interface: defining production readiness expectations for AI workloads, co-owning container security and secrets management with the Security team, and making sure the platform is accessible and well-understood by the product engineering teams that depend on it. Principles that guide us: Focus on the mission: We view software as a means of effecting change in the world, not as an end unto itself. We write software to empower our patients and therapist to better solve the problems they're facing. Ship small, learn fast: We are building new and novel products and believe that we learn what our users need by quickly shipping and iteration Everything is a product: Whether it's our patient search experience or a developer productivity improvement, we treat everything we build at Headway as a product with end-users in mind. Optimize for trust: We believe that engineers should be continually learning. To learn effectively and to be productive, engineers must feel safe asking questions and discussing mistakes. Who You Are We're looking for experienced engineering team leaders and people managers who are relationship-obsessed, drive results, and enable their teams to build for technical excellence. As a Senior Engineering Manager at Headway, you will work closely with Engineering Leadership, Security, and product engineering teams across the org to help shape the future of the engineering organization. You are an infrastructure leader who is as comfortable in a postmortem as you are in a planning doc. You know how to run a team that carries a support queue while still making progress on strategic platform work. You hold the technical bar yourself and earn credibility with the team through the quality of your judgment, not your title. 5-7+ years of experience of engineering leadership experience, with experience leading infrastructure or platform teams. 5+ years of experience as a Software or Infrastructure Engineer, with enough depth to lead credibly in design reviews and incident response You've personally led the shift from "infra team owns everything" to a self-serve platform other engineers build on themselves — not just inherited or operated a system where that transition had already happened. Experience managing the interface between a platform team and the product engineering teams that depend on it, including setting ownership boundaries and building self-serve tooling Comfortable managing through competing demands: a support queue, a strategic roadmap, an on-call rotation, and fast-moving external dependencies all at once Familiarity with cloud infrastructure at scale (AWS), observability tooling (Datadog or similar), and deployment pipelines at companies where reliability is a product requirement. You're personally hands-on with AI coding tools day to day — not just driving your team's AI adoption as a program. Every candidate goes through a hands-on AI coding interview as part of this loop Experience owning a platform strategy and representing it to senior leadership: setting measurable goals for infrastructure work, and making the case for foundational investment in terms the business understands Below are additional experiences we think help engineering managers succeed at Headway: You have led a team through a significant architectural transition, such as moving from a monolith toward service isolation, or from manual to automated operations You have experience building or governing LLM infrastructure and AI platform primitives You have experience in healthcare or another regulated environment 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.

Design secure systems and build infrastructure guardrails while maturing cloud security posture and assisting in incident response and vulnerability management. | Requires 5+ years in security or software engineering with expertise in secure platform building and passion for AI-driven security in a fast-paced environment. | 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 The Security team at Headway is focused on security and privacy for all of Headway’s customers - therapists, patients, and payers (ex: insurance companies and health systems). As an early member on the team, you’ll have the unique opportunity to be the builder and driver of our dedicated, in-house security engineering efforts. In this role, you will partner closely with our engineering teams to ensure that Headway systems are designed and managed securely so that we can maintain and grow customers’ trust in Headway. What you’ll do at Headway: Partner with Product and Infrastructure teams: Headway has many new product launches on the horizon that will transform the industry and have a rich data component. You will be a partner with teams to build platforms and infrastructure that accelerate product development while reducing risk, including (but not limited to): System engineering or implementation efforts Doing security reviews Helping with system design decisions Continuous improvement of Headway's critical infrastructure Make the safe way, the easy way: Work on defining and building infrastructure and application guardrails so that developers can build securely by default. You also will work to instill a culture of secure system design across engineering. Build out and mature Headway's cloud security posture: Build an AI-native approach to configuration standards, hardening, and vulnerability remediation across our AWS footprint. Assist in ongoing security operations: You will be part of the security and have responsibilities to assist in incident response, vulnerability management, security reviews, and other operational tasks to ensure that our security program is operating at a world-class level. Tools we use: AI: Anthropic, Cursor, Langsmith Cloud Security: Wiz, Cloudflare Languages: Python 3, TypeScript Libraries: FastAPI, SQLAlchemy, React Datastores: Postgres, Redis Infrastructure: AWS (Fargate, ECS, K8s, S3, and more) Monitoring: Datadog, PagerDuty Version Control: Github Vulnerability Management: Wiz, Semgrep You’ll be great for this role if you have: Have 0 → 1 security experience: You have 5+ years experience in security and/or software engineering roles with a demonstrated history of working on security-related projects or with responsibilities as a security generalist. Strong cross-functional experience: You love partnering with other teams to help both teams achieve their goals. Strong technical depth and breadth: You have technical experience with building secure platforms and products at a deep level. You are excited to perform security design and code reviews. You want to understand security systems and improve their efficiency and scalability. Excited by AI’s potential: You believe AI will fundamentally reshape how infrastructure security works, and you want to be at the forefront of making that happen. Thrive in ambiguity: You love tackling ambiguous problems in a fast-paced environment with an optimistic and energizing attitude. Innovation at Scale: You seek opportunities to lead the industry in implementing the latest security and privacy technologies. Results driven: You care deeply about creating impact and driving results for Headway’s business. Mission driven: You are motivated by Headway’s mission, increasing access to high quality mental health care. 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.

Lead customer experience operations including agent success, customer care, systems, and manage a large team while driving AI integration and managing capacity and costs. | 10+ years in customer experience or service operations with 5+ years in management and experience managing blended internal and outsourced teams and AI transitions. | 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. Every month, tens of thousands of patients and providers reach out to Headway with a benefit that isn't showing up, a bill that looks wrong, a claim in limbo, or a credentialing application waiting on an answer. Each one is an opportunity to earn trust and strengthen the relationship, not just close a ticket. Customer Experience is responsible for resolving those issues and delivering a quality experience every time. Headway is growing quickly and AI is changing what support can actually resolve, which makes this the moment to reshape how customer experience works in mental health care and set the standard for what it should look like. As Director of Customer Experience (CX) Operations, you will lead the entire CX operation across Agent Success, Customer Care, Programs, and Systems, an operation of more than 100 Headway employees and over 800 partner agents, reporting to the Head of Operations. You will be directly responsible for customer experience at Headway and will represent the function to the executive team. This is a senior leadership role for a driver who can turn ambiguity into clarity, build a high-performing team, and create the support operation a fast-growing consumer healthcare business needs to win. What You'll Do Own the customer experience end to end. You'll set the standard for what great support looks like at Headway for both patients and providers, own the scorecard behind it, and be accountable for how the operation performs. Lead and grow the team. You'll lead teams across Agent Success, Customer Care, Programs, and Systems, spanning more than 100 Headway employees and over 800 partner agents. You'll develop the managers who run them and own hiring and performance across the function. Bring AI into the operation in service of a better experience. Automation should mean faster answers, fewer repeat contacts, and agents spending their time where judgment matters most. You'll co-own that agenda with our Director of Product for CX, decide where it drives the most value and what the operation is ready to support, and set the quality bar it has to clear. Own capacity and cost. Headway is growing incredibly fast, and support demand grows with it. You'll build an operation that scales with that growth: forecasting demand, staffing across internal and outsourced capacity, and holding cost-per-contact targets while quality improves. Build the engine behind great support. Training, quality assurance, the procedures agents work from, and the technology the team runs on are what separate an operation that keeps getting better from one that just keeps up. You'll own all of it. Be the customer's voice inside R&D. Every recurring contact points to something we can fix upstream. You'll bring that evidence to R&D, help shape where investment goes, and push for the fixes that remove support demand rather than absorb it. What You'll Have You have 10+ years in customer experience, support, or service operations and strategy, including 5+ years leading teams of managers. You have run a blended internal and outsourced support organization at the scale of several hundred agents inside a high-growth technology company, managing partners from the client side and holding them to both performance and commercial commitments. You own the cost line, not just service levels, and you are comfortable with demand forecasting, capacity planning, and headcount ownership. You have led a support organization through an AI or automation transition, and you can say why it delivered a better customer experience rather than only a lower cost. You know the CX landscape and tooling stack deeply, including what is genuinely cutting edge, and you're AI-native in how you work. You've rebuilt your own workflows around these tools and have a real point of view on what is worth adopting to transform an operation rather than just adding tools to it. You have partnered closely with R&D, using evidence from your own operation to influence what gets built, and you operate beyond your own function rather than running a siloed org. You care about the patients and providers on the other end of every contact, and you are motivated to advance Headway's mission to make mental healthcare more accessible and affordable across the United States. 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 $160,000-$250,000, 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.

Lead cross-functional initiatives, manage teams, and translate insights into operational plans. | 7+ years operational experience in high-growth environments with strong data analysis and cross-functional alignment skills. | 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 Headway works to build a new mental healthcare system that everyone can access, we’re facing unique operational challenges and opportunities that come with growing and scaling at an unparalleled rate. We’re pushing the boundaries of the existing healthcare system so that we can fulfill our promise to providers, patients, and payers to create access to high quality providers across the nation. In order to do that, we’re building a world class operations team that enables efficiency, growth, and quality, and as a member of this team, you will have the opportunity to have a material impact on the trajectory of Headway and help define a function core to the livelihood of our business and the impact we deliver for our partners and clients. As a Business Operations Manager, you will lead high-impact, cross-functional initiatives that span teams and pods. You’ll operate as a thought partner to Product, Data, and Operations leaders – helping shape objectives, influence priorities, and translate complex insights into actionable plans. In addition to owning critical operational workflows, you’ll design scalable systems, mentor team members, and drive initiatives that create durable, measurable impact across the organization. This role requires strong judgment, comfort with ambiguity, and the ability to drive alignment and execution across the organization. What you’ll do at Headway Design and build foundations for a variety of 0-1 initiatives within the Business Operations function. Collaborate cross-functionally to build, execute, monitor, and implement scalable products and processes that enable us to deliver on core business challenges. Assess and analyze data to develop and determine strategies for accelerating progress, proactively identify areas for improvement, and deliver on roadmap priorities and team OKRs. Build and manage a growing team to achieve these objectives. You’ll be great for this role if you: 7+ years of experience in operational roles at high-growth companies, with some background in consulting, finance, business operations preferred but not required. Data is your first-language; you enjoy and are skilled at digging through complex data to solve ambiguous problems. You thrive in the unknown, and seek out opportunities to dive into unfamiliar challenges, drive towards outcomes, and shape strategy. You are operationally excellent, able to manage a large volume of moving pieces without breaking a sweat. You are a collaborator that proactively partners across teams while holding teams accountable for business results. You seek an environment that fosters individual growth through open-feedback and high-autonomy. You are motivated by the opportunity to make an impact on one of our generation’s defining problems: affordable mental healthcare Compensation and Benefits: The expected base pay range for this position is $121,600 - $190,000 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.

Lead design and implementation of insurance systems including patient identification, pricing, and claims processing, and mentor engineering team members. | Requires platform-oriented engineer with deep experience in reliable systems for complex data, hands-on coding, strong communication, and ownership of ambiguous problems from design to production. | 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.

Partner with product and engineering teams to ensure secure application design and development, build security tooling, and assist in security operations. | 5+ years in security or software engineering with security-related responsibilities, strong cross-functional and technical skills, and enthusiasm for AI in security. | 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’s mission is a big one – to build a new mental health care system everyone can access. We’ve built technology that helps people find great therapists with the first software-enabled national network of providers accepting insurance. 1 in 4 people in the US have a treatable mental health condition, but the majority of providers don’t accept insurance, making therapy too expensive for most people. Headway is building a new mental healthcare system that everyone can access by making it easy for therapists to accept insurance and scale their practice. Headway was founded in 2019. Since then, we’ve grown into a diverse, national network of over 60,000 mental healthcare providers across all 50 states who run their practice on our software and have served over 1 million patients. We’re a Series D company with over $325m in funding from a16z (Andreessen Horowitz), Accel, GV (formerly Google Ventures), Spark Capital, Thrive Capital, Forerunner Ventures and Health Care Service Corporation. 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 The Security team at Headway is focused on security and privacy for all of Headway’s customers - therapists, patients, and payers (ex: insurance companies and health systems). As an early member on the team, you’ll have the unique opportunity to be the builder and driver of our dedicated, in-house product and application security engineering efforts. In this role, you will partner closely with our product and engineering teams to ensure that our application is designed and developed securely so that we can maintain and grow customers’ trust in Headway. What You’ll Do At Headway • Partner with Product and Engineering: Headway has many new product launches on the horizon that will transform the industry and have a rich data component. You will be a partner at both the design and development stage to ensure that we implement new features securely, including (but not limited to): • Participating in the implementation efforts • Doing security reviews • Helping with product design decisions • Auditing and surfacing vulnerabilities in our current products • Build Agentic Security Tooling: Move beyond rules-based automation to agentic workflows that address potential code problems at scale across our rapidly growing codebase. You'll help define what AI-native product security looks like at Headway. • Make the safe way, the easy way: Work on defining and building application guardrails so that developers can build securely by default. You also will work to instill a culture of secure development across engineering. • Assist in ongoing security operations: You will be part of the security and privacy team and have responsibilities to assist in incident response, vulnerability management, penetration testing, security reviews, and other operational tasks to ensure that our security program is operating at a world-class level. Tools We Use • Cloud Security: Lacework • Languages: Python 3, TypeScript • Libraries: FastAPI, SQLAlchemy, React • Datastores: Postgres, Redis • Infrastructure: AWS (Fargate, ECS, S3, and more), Spark and Kafka • Monitoring: Datadog, PagerDuty • Version Control: Github • Vulnerability Management: Snyk, Semgrep You’ll be great for this role if you have: • Have 0 → 1 security experience: You have 5+ years experience in security and/or software engineering roles with a demonstrated history of working on security-related projects or with responsibilities as a security generalist. • Strong cross-functional experience: You love partnering with other teams to help both teams achieve their goals. • Strong technical depth and breadth: You have technical experience with building secure platforms and products at a deep level. You are excited to perform security design and code reviews. You want to understand security systems and improve their efficiency and scalability. • Excited by AI’s potential: You believe AI will fundamentally reshape how product security works, and you want to be at the forefront of making that happen. • Thrive in ambiguity: You love tackling ambiguous problems in a fast-paced environment with an optimistic and energizing attitude. • Innovation at Scale: You seek opportunities to lead the industry in implementing the latest security and privacy technologies. • Results driven: You care deeply about creating impact and driving results for Headway’s business. • Mission driven: You are motivated by Headway’s mission, increasing access to high quality mental health care. 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 round: You'll meet with a member of our Security Engineering team for introductions and an architecture interview. Conducted similarly to a System Design interview, we’ll learn more about your knowledge of the role of security in engineering systems and web architecture. • Final rounds: You’ll meet several more team members for technical and non-technical interviews and leave with a fuller picture of what it’s like to work at Headway. • References and the Offer: Our favorite part of the process! We'll send over all of the details, including specifics on employee equity, and congratulatory messages from excited future team members! Compensation & Benefits The expected base pay range for this position is $218,500 - $273,125, 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. Compensation Range: $222.5K - $278.5K