Head Of People

About Gray Swan

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.

Learn more about how we work.

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.

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 requirements apply at each stage, where the risk is, and how to build the right processes before we need them.

• Benefits and HR systems: You’ll lead benefits strategy and our HRIS and people platforms, and make sure both can support a larger, more distributed company.

This is a senior leadership role. You’ll report to Gray Swan’s VP of Operations and partner with leadership on headcount planning, org design, compensation and people strategy. You’ll have a clear path to growth as you demonstrate that you are helping Gray Swan scale effectively.

This role is in-person at our Pittsburgh office, four days per week. We provide relocation support.

What You'll Do

Lead compliance as we scale

• Manage the requirements for hiring in new states and countries, including registration, payroll tax, leave, final pay and pay transparency rules

• Track headcount thresholds as we grow and prepare for the laws that come with them, such as Title VII and ADA at 15 employees, COBRA at 20, FMLA and the ACA employer mandate at 50, and EEO-1 and WARN at 100

• Set and review classifications (contractor vs. employee, exempt vs. non-exempt) so they hold up as the company changes

• Own our policies and handbook, required postings and required reporting (EEO-1, ACA)