People Operations Lead

Prosper Health • New York, NY

5d • Remote

About The Position

Prosper Health is seeking a People Operations Lead to build and scale the people systems necessary for the company's growth from 350 to over 1,000 clinicians within the next 12 months. As the inaugural hire for people operations, this role will establish the function from the ground up, taking ownership of the entire people operations spectrum, including employee relations, performance management, lifecycle operations, compliance, and compensation systems. The position reports to the Head of Clinical Operations, focusing on transforming people-related challenges into efficient, scalable processes that support rapid company expansion while safeguarding the organization. This role demands a high degree of ownership and sound judgment, involving direct management of investigations, coordination with the PEO, administration of pay and benefits, and handling accommodation requests. Simultaneously, the individual will be responsible for creating repeatable and scalable playbooks, decision trees, and templates for people operations, designing systems capable of supporting over 1,000 clinicians. The ideal candidate will be motivated by first-principles thinking, high-stakes problem-solving, and the creation of durable systems in a dynamic environment.

Requirements

• 6-8+ years of experience in people operations or human resources within a startup, consulting, or high-growth operational roles
• Direct exposure to employee relations and pay/benefits administration
• First-principles thinker: Don't default to "HR best practices"—dig into what's actually driving people problems, identify what needs to be solved versus what's nice-to-have, and build practical solutions for our context
• Builds for scale: Design processes that can handle 1,000+ clinicians, thinking through edge cases, failure modes, and handoff points rather than one-off solutions
• Sound judgment: Apply good judgment in messy, high-stakes situations (performance issues, investigations, terminations); know when consistency matters versus when nuance is required
• High ownership: Extremely organized and reliable; own the full people ops surface area, ensure nothing falls through the cracks, and escalate when issues carry material legal, financial, or operational risk
• Bias for action: Move quickly to contain people issues and establish clarity without creating downstream risk; comfortable with testing and iteration rather than perfect upfront design
• Hands-on with systems: Comfortable managing PEO administration, payroll coordination, compensation data in Excel, and building trackers and formulas to identify trends

Responsibilities

• Operate company-wide people systems: Own PEO administration, payroll coordination, benefits administration, and policy documentation, ensuring clean execution across all employee lifecycle events
• Scale clinician lifecycle operations: Streamline onboarding, leaves of absence, exits, and role/status changes; partner with Clinical Ops and Provider Growth to support rapid scaling to 1,000+ clinicians
• Support compensation planning: Conduct competitive market reviews, help create pay bands and raise frameworks, and ensure compensation changes are executed cleanly
• Lead employee relations end-to-end: Manage investigations, terminations, accommodations, and documentation in a way that is fast, calm, and legally defensible, containing issues before they escalate
• Build clinician performance management systems: Design and run playbooks, decision trees, and templates so most performance issues are resolved without CEO or Head of Clinical Ops involvement
• Build corporate people systems: Work directly with the CEO to establish consistent processes for the corporate team, including onboarding/offboarding, performance management, and structured feedback

Benefits

• Health insurance
• Dental insurance
• Vision insurance

What This Job Offers

• Job Type: Full-time
• Career Level: Mid Level
• Education Level: No Education Listed