Headway

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

Lead AI-powered talent acquisition enablement programs and manage employee referral initiatives to optimize hiring workflows. | Experience with enablement programs, AI tools, LLMs, and managing complex cross-functional programs in recruiting contexts. | 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 Headway is hiring a Senior TA Program Manager, AI Enablement, to build the programs, and the AI-powered systems behind them, that make our TA team and hiring ecosystem measurably more effective. This role sits at the intersection of two of the most important things happening at Headway: a significant tooling and process transformation in Talent, and a company-wide commitment to AI adoption where every Headwegian is accountable to a measurable benchmark. This isn't a training-room-only role. You'll lead the end-to-end implementation of AI-powered solutions across TA workflows, from scoping and design through piloting, launch, and iteration, growing your building range as you go. You'll be a program owner, a coach, and a change agent embedded within the Talent team helping to transform how Headway hires. You Will Own hiring manager and interviewer enablement end-to-end Lead end-to-end implementation of AI-powered solutions and programs across TA workflows, from scoping and design through piloting, launch, and iteration Own Headway’s employee referral program, redesigning the program to activate our existing Headway employee network into a high-quality talent source Partner cross-functionally across the organization to strengthen Headway’s talent brand to help drive our candidate pipeline goals to support hiring at scale Design, launch, and scale TA enablement programs, recruiter skill development, tooling onboarding, and documentation that scales with a high-volume, fast-paced hiring environment, increasingly powered by agentic workflows you create Define success metrics for every program you own; your KPIs will include end users enabled, AI-powered solutions shipped, and sustained adoption across TA and hiring teams, with dashboards that make enablement ROI visible Pilot and scale AI-assisted approaches across recruiting tasks: job description writing, candidate screening support, interviewer prep, and communication drafting Champion responsible AI use, partnering with Legal, Compliance, and IT to establish guardrails and ensure AI-assisted hiring workflows comply with data privacy standards and employment law Gather feedback, read the signal, and iterate on your programs and the workflows underneath them You'd Be a Great Fit If… You've owned enablement or learning programs end-to-end - designed the experience, managed the rollout, measured the impact, and iterated AI tools are genuinely part of how you work today - you use them, you have opinions about them, and you're already experimenting with building workflows and automations (and eager to go deeper) You can craft effective prompts across varied workflows and understand how LLMs work well enough to teach others and quality-check their outputs You're comfortable getting hands-on with AI tools and real data (an ATS, a tooling stack) to make outcomes visible You bring structure to ambiguity You've worked in or closely alongside Talent Acquisition and understand the Recruiter's workflow—what makes it harder or easier You have a strong yet adaptable communication style and can tailor it for different audiences You have managed complex, cross-functional programs with multiple stakeholders and competing timelines and have a system for keeping things on track You are as comfortable in a project tracker and a stakeholder update as you are in a workshop or a pilot Compensation and Benefits: The expected base pay range for this position is $115,000- $179,000, 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.