Head of Talent and People (backed by Y Combinator, $5M+ ARR, $23M+ raised)

Location: San Francisco Workplace: OnSite 🧠 ABOUT LEGION HEALTH At Legion Health https://legionhealth.com/, we believe everyone deserves fast, affordable, and world-class health care, and we’re developing the AI infrastructure to deliver it ourselves at world scale. Legion is building autonomous medical care (the AI doctor), starting with psychiatry. Our AI-native care-delivery platform currently automates 95% of the administrative work required for us to deliver direct patient care. We also recently became the first company ever to receive regulatory authorization to let AI prescribe psychiatric medications https://nypost.com/2026/03/27/business/artificial-intelligence-can-now-prescribe-mental-health-drugs/, allowing us to not only collapse health care’s admin costs but also its clinical labor costs—shifting this industry’s economics from humans to tokens. Our technical moat is hard to copy—we combine rich data, production AI, doctors in the loop, and end-to-end care operations to deliver measurably better care to a clinically complex patient population. This has helped us produce tens of thousands of total visits in just 2 years, all while holding ops costs flat and achieving industry-leading patient NPS and retention. While the last generation of healthcare startups made the existing system incrementally more efficient, Legion is rebuilding full-stack care delivery from first principles. Our vision? A 10X better patient experience that’s higher quality, less expensive, and more scalable than ever before. And a 10X better clinician experience that frees our providers to focus on what matters most: caring for patients. Legion Health is backed by Y Combinator, leading venture capital firms, and founders from Function Health, Modern Health, Everly Health, Trusted Health, Clipboard Health, PatientPing, Sesame Care, Faire, EasyPost, and fuboTV. Join us as we build the future of health care: faster, higher-quality, and more affordable, powered by doctors and AI working together. 📍 ROLE LOGISTICS - Job Type: Full-Time - Role Type: People / Talent / Recruiting / People Operations - Ideal Experience Level: 5+ years - Location: San Francisco - Work Setup: In person in San Francisco; this is not a remote role - Reports To: Co-founder and CEO - US Visa Sponsorship: Yes 🚀 THE OPPORTUNITY Legion is hiring a Head of Talent and People to build the talent engine and people operating system behind a category-defining healthcare company. You will be the senior-most owner of People and Talent at Legion. You will own the entire employee journey—from the first outbound recruiting message through interviews, closing, relocation, onboarding, performance, development, compensation, engagement, and eventual offboarding. This is an unusually broad, hands-on leadership role. In the same week, you might personally source an exceptional AI engineer, close a senior operator, coach a manager through difficult feedback, review payroll, coordinate an employee’s move to San Francisco, improve onboarding, and produce a company dinner or offsite. You will not inherit a large recruiting or HR team. During the first 12–18 months, you are the team: the lead recruiter, People operator, culture builder, employee-experience owner, and trusted adviser to the founders. You will build systems and eventually hire support only where the company’s scale and bottlenecks justify it. The right person combines the talent instincts of an elite startup recruiter, the operational precision of an exceptional People leader, the judgment of a trusted executive partner, and the warmth of someone who genuinely enjoys creating an extraordinary place to work. This is not a role for someone who wants to advise from a distance, manage a team of recruiters, or hand execution to vendors. We need a player-coach who can build the strategy, open Ashby, source candidates, close offers, fix broken processes, and personally make sure every new employee has a laptop and a great first day. ✅ RESPONSIBILITIES AND DELIVERABLES - Own Legion’s company-wide talent plan: translate business priorities, product roadmaps, clinical expansion, and organizational constraints into a sequenced hiring plan with clear role priorities, scorecards, timelines, and accountable hiring managers. - Personally run full-cycle recruiting across AI and engineering, product, consumer growth, operations, finance, clinical leadership, executive, and other hard-to-fill roles—from role kickoff and sourcing through assessment, references, offer negotiation, and close. - Build exceptional outbound pipelines. Identify and engage high-performing passive candidates through targeted research, personalized outreach, referrals, communities, events, founder networks, and persistent relationship-building. - Create a rigorous hiring standard for every role: outcome-based scorecards, calibrated interview plans, structured questions, useful work samples, interviewer training, evidence-based debriefs, references, and explicit hiring decisions. - Become a compelling closer. Understand what motivates each candidate and thoughtfully navigate compensation, equity, risk, mission, career trajectory, immigration, relocation, counteroffers, family considerations, and other barriers to joining an early-stage company. - Deliver an unusually strong candidate experience: fast communication, organized scheduling, prepared interviewers, honest expectations, thoughtful selling, clear decisions, and respectful rejection. - Build Legion’s employer brand and talent narrative across job descriptions, recruiting content, founder channels, employee stories, events, referrals, candidate materials, and targeted communities. - Own recruiting operations and analytics, including Ashby configuration, pipeline integrity, scheduling workflows, templates, agency management, recruiting spend, weekly talent reviews, forecasting, and hiring-manager accountability. - Measure recruiting performance using metrics that matter: quality of hire, source quality, qualified pipeline, conversion by stage, time in stage, time to fill, offer acceptance, hiring-manager responsiveness, candidate experience, retention, and agency dependence. - Own the complete employee lifecycle: offers, employment agreements, background checks, work authorization, onboarding, employee records, status changes, leaves, promotions, compensation changes, transfers, departures, and offboarding. - Run reliable payroll and payment operations for employees and contractors. Coordinate payroll changes, bonuses, deductions, reimbursements, commissions where applicable, tax registrations, and issue resolution accurately and on time. - Own the operating relationship with benefits, payroll, HRIS, equity, immigration, background-check, employment-law, and other People vendors. Hold every partner accountable for service, accuracy, cost, and employee experience. - Administer and continuously improve medical, dental, vision, leave, retirement, wellness, and other benefit programs, ensuring employees understand and can actually use what Legion provides. - Partner with finance and leadership on compensation philosophy, salary bands, equity practices, offer construction, promotions, market calibration, headcount planning, and People budgets. - Build pragmatic People infrastructure: policies, handbook, compliance calendar, employee files, required notices, training, reporting, approval workflows, templates, manager resources, and a clear source of truth. - Coordinate with qualified employment, immigration, benefits, tax, and other counsel to manage California and multi-state employment requirements, worker classification, accommodations, leaves, investigations, immigration, terminations, and other sensitive matters. You are not expected to be Legion’s lawyer, but you are accountable for recognizing risk early and getting the right advice. - Handle employee relations with discretion, fairness, speed, and sound judgment. Support investigations, performance concerns, interpersonal conflict, accommodations, conduct issues, improvement plans, and departures without avoiding difficult decisions. - Build a high-quality performance system: clear expectations, direct feedback, regular check-ins, talent reviews, manager calibration, development plans, promotion decisions, recognition, and decisive intervention when performance falls below Legion’s standard. - Help leadership design the organization as it scales: roles, reporting lines, spans of control, responsibilities, decision rights, succession risk, management capacity, and where the company should hire, develop, redesign, or part ways. - Coach founders and managers to become exceptional talent leaders. Help them set expectations, give feedback, interview effectively, make difficult calls, recognize excellent work, and build teams with high talent density. - Own relocation to San Francisco for new and existing employees. Design the policy and coordinate immigration, travel, temporary housing, moving support, reimbursements, payroll and state transitions, family considerations, and local onboarding from signed offer through successful arrival. - Make every employee operationally ready on Day 1. Coordinate laptops, accessories, mobile-device management, software, email, permissions, security access, account provisioning, workspace, onboarding schedules, equipment inventory, replacements, and returns. - Build an onboarding experience that accelerates time to impact: preboarding, company context, role-specific plans, compliance and security training, manager preparation, introductions, 30/60/90-day expectations, and structured feedback. - Own the San Francisco employee and workplace experience, including office operations, meals, supplies, vendors, workspace readiness, candidate onsite visits, safety, and the details that allow the team to do excellent work. - Create memorable internal experiences: team dinners, celebrations, launches, traditions, learning sessions, retreats, offsites, community events, and other moments that make Legion demanding, energizing, and fun. - Own the operating details behind company events, including objectives, budgets, venues, travel, vendors, accessibility, communications, attendance, execution, and post-event feedback. - Build effective internal communications so employees understand company priorities, organizational changes, new hires, policies, decisions, expectations, and the reasoning behind them. - Listen to the organization without becoming governed by surveys or consensus. Use direct conversations, employee feedback, manager input, operating data, and judgment to identify risks and improve the employee experience. - Use AI aggressively and responsibly to improve sourcing, outreach, scheduling, documentation, onboarding, employee self-service, People analytics, knowledge management, and repetitive administration while protecting confidential employee and candidate information. - Build the People and Talent team over time. Hire recruiters, coordinators, People operators, workplace support, or specialist partners only when the data and organizational needs justify additional leverage. 🏆 YOU’LL BE SUCCESSFUL IF YOU… - Within your first 30 days, you understand Legion’s business, team, open roles, hiring constraints, compensation practices, People systems, vendors, organizational risks, and most urgent operational gaps. - Every priority opening has a clear scorecard, calibrated interview process, accountable hiring manager, sourcing strategy, recruiting owner, and realistic closing plan. - Within 90 days, Legion has consistent outbound pipelines for its hardest roles, a disciplined weekly talent review, reliable recruiting data, and substantially less founder time lost to scheduling and recruiting administration. - Candidates move through Legion’s process quickly, encounter prepared interviewers, receive clear communication, and leave with a stronger impression of the company regardless of the final decision. - Legion consistently hires unusually capable people rather than merely filling seats. Quality of hire and long-term talent density remain more important than raw hiring volume. - Offers close because candidates understand Legion’s mission, expectations, upside, risks, compensation, equity, working environment, and the extraordinary opportunity in front of them. - Every new hire arrives in San Francisco with relocation barriers addressed and begins Day 1 with the necessary equipment, access, schedule, context, relationships, and expectations. - Payroll, benefits, employee records, compliance deadlines, equity coordination, equipment, onboarding, and offboarding operate reliably without recurring surprises or manual heroics. - Managers give clearer feedback, address performance problems earlier, interview more effectively, and make better organizational decisions because of your coaching and systems. - Legion develops a practical compensation, leveling, performance, and promotion framework that employees and managers can understand without creating unnecessary bureaucracy. - Company events and rituals strengthen trust, connection, energy, and shared purpose rather than feeling like obligatory corporate programming. - You identify organizational, compliance, employee-relations, and retention risks before they become crises, and leadership trusts you to handle sensitive situations with discretion and courage. - You build a People function that is highly responsive and deeply human while remaining operationally rigorous, analytically grounded, and appropriately lean. - AI and automation eliminate meaningful administrative work without degrading candidate experience, employee trust, data security, or decision quality. - Twelve months from now, Legion has measurably higher talent density, a more predictable recruiting engine, stronger managers, faster onboarding, clearer expectations, and substantially less reactive People work sitting with the founders. 🧰 IDEAL BACKGROUND AND SKILLS - 5+ years of progressively responsible experience spanning recruiting, talent leadership, People Operations, HR, or organizational leadership at high-growth technology companies. - Experience serving as the first, early, or senior-most People and Talent hire at a venture-backed startup—ideally while scaling from approximately 25–50 employees to 100–150+. - Demonstrated success personally sourcing, assessing, and closing exceptional passive candidates for difficult roles. You are still energized by recruiting and do not consider sourcing or coordination beneath your level. - Strong technical-recruiting ability across AI, engineering, data, and product, plus the versatility to recruit consumer growth, operations, clinical leadership, finance, and executive talent. - Evidence that your hires became high-performing, durable members of the organization—not simply that you hit an annual hiring number. - Experience building recruiting infrastructure from zero or rebuilding an inconsistent system: workforce planning, scorecards, structured interviews, interviewer training, referrals, sourcing operations, analytics, employer branding, and closing. - Hands-on People Operations experience across payroll, benefits, HRIS, employee records, equity administration, onboarding, offboarding, leaves, policies, vendor management, and compliance. - Sound working knowledge of California and multi-state employment practices, with the judgment to identify when specialized employment, immigration, tax, or benefits counsel is required. - Experience managing sensitive employee-relations matters, investigations, performance improvement, terminations, accommodations, organizational changes, and other high-stakes situations. - Experience designing or operating compensation bands, leveling, performance reviews, promotion processes, talent reviews, manager training, and workforce planning. - Excellent judgment under ambiguity. You can balance speed, consistency, empathy, legal risk, individual circumstances, and company standards without hiding behind policy. - Strong analytical fluency. You can build dashboards, diagnose funnel problems, forecast hiring capacity, audit compensation, evaluate vendors, and distinguish useful People data from vanity metrics. - Comfortable with tools such as Ashby, Rippling, Gusto, Justworks, Deel, Carta, Pave, Slack, Notion, Google Workspace, modern device-management systems, and AI tools for sourcing, analysis, automation, and documentation. - Exceptional written and verbal communication. You can write a compelling outbound message, a precise policy, a sensitive employee communication, a strong job description, and a clear executive recommendation. - High discretion and unquestioned integrity. People trust you with information that cannot be mishandled, politicized, or casually shared. - High warmth and high standards. You care deeply about people without confusing care with avoiding accountability or lowering the bar. - Strong hospitality and event instincts. You notice the operational details that make interviews, first days, dinners, retreats, and the everyday workplace feel intentional. - Low ego, high urgency, and founder-level ownership. You can set a talent strategy Monday, source candidates Tuesday, fix payroll Wednesday, coach a manager Thursday, and run an exceptional team event Friday. - Willing and excited to work in person in San Francisco and to help build an in-person culture with exceptional energy, trust, and execution. - Especially valuable: Experience in healthcare, regulated technology, AI, clinician recruiting, mixed employee/contractor workforces, immigration, relocation, workplace operations, or rapid office-based scaling. 💰 COMPENSATION & BENEFITS - Salary: $170,000–$260,000, based on experience - Early-Stage Equity: Meaningful ownership in a category-defining company - Health Insurance: Medical, dental, and vision benefits - Relocation: Support for moving to San Francisco - US Visa Sponsorship: Available for exceptional candidates - Additional Perks: In-person retreats, company events, meal stipends, AI tooling, and professional-development support - Time Off: Flexible, unlimited vacation policy - Work Hours: Flexible, with the responsiveness and intensity expected from a company-building leadership role - Work Setup: In person in San Francisco; this role owns a meaningful part of Legion’s in-person employee experience - Impact: Build the team and operating environment behind a company trying to change health care forever - Autonomy and Learning: Own People and Talent end-to-end, with direct access to the founders and visibility into every part of the company - Growth Opportunities: With exceptional performance and company growth, this role can develop into VP of People and Talent, Head of People, or another executive leadership position. 📝 HOW TO APPLY AND HIRING PROCESS - Apply here: https://jobs.ashbyhq.com/legionhealth/3f5d8943-7668-4546-8373-54b56b951341/application - Overview of our hiring process: 1. Resume + Application Screen 2. Founder Interview 3. Live Working Session or Case Study 4. Onsite Cross-Functional Interviews with Founders 5. Professional Reference Checks, including former executives, peers, internal customers, and direct reports where applicable - Estimated time-to-hire: 2 weeks - Start date: ASAP - Hiring manager: Yash Patel, CEO 🤝 EQUAL EMPLOYMENT OPPORTUNITY Legion Health is proud to be an Equal Opportunity Employer. We celebrate diversity and are committed to creating an inclusive environment for all employees, contractors, and applicants without regard to race, color, religion, sex, sexual orientation, gender identity or expression, national origin, age, disability, veteran status, genetic information, or any other protected characteristic under applicable law. We encourage applicants from all backgrounds to apply. Pursuant to the San Francisco Fair Chance Ordinance, Legion Health will consider for employment qualified applicants with arrest and conviction records. Legion Health is committed to providing reasonable accommodations to qualified individuals with disabilities throughout the application and interview process. Applicants who require an accommodation should inform their recruiting contact.