Title: People Ops Generalist

Location: Santa Monica or NYC (Hybrid)

Reporting Structure: VP of People, Mallory

Company Description

Healthcare reimbursement is broken - too complex, too opaque, and too often unfair to the providers delivering care and the patients receiving it.

Pivotal Health exists to fix that. We build technology that helps hospital-based providers get paid fairly for the care they provide, while protecting patients from surprise medical bills. Our platform guides providers through the highly complex No Surprises Act dispute process, turning what was once manual, risky, and inconsistent into a structured, data-driven workflow.

With a rapidly growing customer base, strong revenue momentum, and a mission rooted in fairness and transparency, Pivotal is helping modernize one of healthcare’s most critical—and overlooked—systems.

About the Role

We’re hiring a People Operations Generalist to own the systems, processes, and day-to-day infrastructure that make the employee experience work at Pivotal. You’ll sit at the center of everything: onboarding, compliance, Rippling, Ashby, benefits, and the operational backbone of a scaling People team.

This is a high-ownership, high-visibility role reporting directly to the VP of People. You’ll be our first dedicated People Ops hire, which means you’ll have real influence over how the function is built as we grow to 150 employees and beyond.

Responsibilities

Onboarding & Offboarding

• Own end-to-end onboarding coordination: I-9s, Day 1 prep, and new hire checklist management
• Maintain and improve the onboarding program as we scale
• Manage offboarding operational processes with care and consistency

People Systems & Data

• Own Rippling: employee data, system integrations, access provisioning, and ongoing admin
• Support Ashby configuration: interview scheduling, rec IDs, pod setup, and automation
• Build and maintain People and talent dashboards and hiring metrics for leadership reporting

Compliance & HR Operations

• Track and follow up on compliance items: training completion, benefits enrollment, payroll setup
• Manage background check process and ensure documentation is current
• Support benefits administration, open enrollment, and employee questions
• Maintain accurate records in Rippling and flag issues proactively

Recruiting Operations Support

• Support the Recruiting team with coordination overflow during high-volume periods
• Prepare and send offer letters
• Pull recruiting reports: time-to-fill, pipeline status, agency activity

People Team Operations

• Serve as a first point of contact for routine employee HR inquiries, providing guidance on HR policies, benefits, and People processes
• Own Notion-based People knowledge base: policies, guides, process documentation
• Help build scalable processes as we grow: things that work at 50 employees often don’t at 150

Technology & Process

• Leverage AI tools to streamline administrative tasks, improve knowledge management, and enhance employee self-service resources
• Partner cross-functionally with Finance, IT, and Legal on compliance and process improvements
• Document and standardize SOPs to create scalable, repeatable processes
• Continuously evaluate People systems and tools to improve efficiency, employee experience, and data accuracy

Is this you?

• 3-5 years in People Ops, HR Operations, or a generalist HR role, ideally at a startup or high-growth company
• Hands-on experience with Rippling or a comparable HRIS (Workday, Gusto, Bamboo)
• Familiarity with ATS tools; Ashby experience is a plus
• Strong attention to detail: you catch things, follow through, and don’t let items fall through the cracks
• Comfortable operating in ambiguity and building process where little exists
• Excellent communicator who can explain benefits enrollment to a new hire and a compliance issue to legal in the same day
• Genuinely curious about HR technology, automation, and how AI can make People teams more effective

Extra Credit Experience

• Background in healthcare, healthtech, or a regulated industry
• Experience supporting a People function through a high-growth scaling phase (50 to 150+ employees)

#Perks

• Competitive compensation, including equity: $80K – $100K 
• Full health, dental, and vision coverage
• Retirement savings plan through 401(k)
• Flexible time off
• Opportunities for company-wide connection and events