VP, People & Talent

About the role

We are looking for a hands-on VP, People & Talent to be the first dedicated hire owning recruiting, people operations, and culture at Flagler Health. This is a foundational role. You will not inherit a team, a playbook, or a set of processes. You will build them. You will directly own full-cycle recruiting across engineering, product, GTM, clinical, and G&A functions while simultaneously standing up the people systems (onboarding, performance, compensation, compliance) that a company at this stage needs to scale with intention. This role reports directly to the CEO and is expected to be in-office at least three days per week in New York City. Full-Cycle Talent Acquisition Own Recruiting End-to-End: Run the full lifecycle for every open role, from intake and role design with leadership through sourcing, screening, interviews, offer negotiation, and close. You are the recruiting engine for the company. Build Diverse, High-Quality Pipelines: Act as your own headhunter. Design and execute creative outbound sourcing strategies that reduce dependency on agencies and inbound volume. Healthcare AI talent is niche, and you know how to find people who are not actively looking. Raise the Interview Bar: Design and coach leadership on structured, evidence-based interviewing that evaluates for mission alignment, adaptability, and long-term potential, not just resume pattern matching. Close with Conviction: Navigate complex offer negotiations including equity education and comp benchmarking in a competitive market. Maintain a high acceptance rate by ensuring candidates feel informed, respected, and genuinely excited about Flagler. Scale the Hiring Plan: Partner with the CEO and department leads to translate business goals into a hiring roadmap. You will help the company move from 28 to 50+ headcount this year. That means prioritizing which roles to open, sequencing searches, and moving fast without sacrificing quality. People Operations & Partnership Build the Foundation: Stand up core people infrastructure from scratch: onboarding programs, an employee handbook, compliance frameworks, benefits administration, and HRIS/ATS workflows. You will choose and implement the tools. Performance & Growth: Design and launch a lightweight, stage-appropriate performance management framework. Ensure feedback loops are real, calibration conversations happen, and the bar for performance stays high as the team grows. Compensation & Equity: Own compensation philosophy and benchmarking. Build a comp framework that is competitive, fair, and sustainable at the company's current stage, including equity education for candidates and employees. Leadership Coaching: Serve as a trusted advisor to leaders across the company on team dynamics, personnel decisions, org design, and how to manage effectively as roles and teams evolve. Culture Stewardship: Be the person who protects and shapes Flagler's culture as headcount doubles. Help define values, rituals, and norms that scale without becoming performative. Compliance & Risk: Ensure Flagler stays ahead of employment law requirements across all operating states. Build policies that protect both the company and its employees. About You You are a builder who thrives on ownership. You have done this before at an early-stage company, likely as the first or second people/talent hire, and you know what it feels like to simultaneously run five searches, troubleshoot an onboarding gap, and advise a founder on a tough personnel call. You have an investigative instinct for talent: you look past polished resumes to find the real evidence of high performance, adaptability, and mission fit. You treat every candidate with dignity and every leadership conversation with candor. You are energized, not overwhelmed, by the pace and ambiguity of a company scaling this fast.