Startups · AI

Head of People

Grayswan · Pittsburgh · Remote

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About Grayswan

Gray Swan provides enterprise-grade security solutions for LLMs, developed by the pioneers of AI vulnerability research. Deploy AI with confidence using just two lines of code. Backed by Madrona.

About the role

We’re hiring a Head of People Operations to help shepherd us through our next phase of growth. We're looking for someone who has scaled a fast-growing company across multiple states, supporting both in-person and remote teams. You know what changes in people operations as a company scales, and you know how to get ahead of it. Found on 1752vc Careers, the job board for startup and VC roles.

What they're looking for

  • Experience scaling a fast-growing company (ideally in tech) across multiple states, with both in-person and remote employees
  • 8+ years of progressive HR experience, including 2+ years leading a people function or team
  • Strong working knowledge of FLSA, FMLA, ADA, Title VII, ADEA, ERISA/COBRA, ACA, NLRA and WARN
  • Deep fluency in benefits planning: plan design, brokers and carriers, renewals, budgeting and multi-state coverage
  • Experience choosing and implementing HRIS and payroll platforms
  • Experience leading teams that run recruiting and people operations
More about this role

Gray Swan is on a mission to empower the world to use AI safely and securely. We evaluate AI models for the leading frontier labs along with building real-time threat detection and adaptive adversarial red teaming agents for enterprise teams deploying AI.

We're a team of approximately 50 people, well-funded and growing quickly. Our work directly influences how the world deploys AI agents and systems at scale.

We’re hiring a Head of People Operations to help shepherd us through our next phase of growth. We're looking for someone who has scaled a fast-growing company across multiple states, supporting both in-person and remote teams. You know what changes in people operations as a company scales, and you know how to get ahead of it.

You’ll lead the whole People function. Our hiring function and our People Operations Manager will report to you. They handle day-to-day recruiting, onboarding, culture and employee support. Your job is to lead the function, set direction and make sure we're all equipped for the growth ahead.

Your biggest impact will be in two areas where we need experienced leadership now:

Compliance: You’ll own employment compliance as we scale. You’ll know which...

Read the full posting on Grayswan's site ↗

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