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 grayswan.ai.
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)
- Lead high-risk employee matters: investigations, terminations, leave and accommodation cases, agency charges and any reductions in force. Know when to bring in outside counsel
- Find and close existing compliance gaps
Lead benefits and HR programs
- Own our HRIS, payroll and people platforms. Evaluate whether our current tools will hold up as we grow, choose new ones when needed, and set our people data strategy
- Own benefits strategy, plan design and budget. Choose and manage brokers and carriers, and lead renewals
- Build a benefits program that stays competitive and compliant (ERISA, COBRA, ACA) as headcount and locations grow, including multi-state and international coverage
Inform compensation
- Help shape our compensation philosophy, salary bands and equity guidelines as we scale, using your market knowledge and experience
- Make sure pay practices comply with pay transparency and equal pay laws, and run pay equity reviews
Lead the People function
- Develop the People and Talent Teams by coaching and growing these functions and building capabilities and structure of People Operations as the company scales
- Provide insight and direction on our people programs, from hiring and onboarding to performance reviews, so they can grow with the company, both in person and remote
- Partner with leadership on headcount planning, org design and people strategy, and advise on people risk
Who You Are
- 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
- Good judgment on when to bring in employment counsel, and a practical approach where compliance helps the business move
- Able to work in person in Pittsburgh (relocation support available)
Preferred
- Experience with international hiring, such as employer of record, visas and global benefits
- Experience shaping compensation and equity frameworks at a growing startup
- SHRM-SCP or SPHR certification
What We Offer
We offer a competitive compensation package designed to reward impact and incentivize growth. Our compensation philosophy is informed by our current valuation and recent industry data. Compensation: $155,000 - $245,000 plus performance-based bonus and meaningful equity package
BENEFITS:
- 401k with up to 4% matching
- 28 days annual leave (vacation + holidays)
- Health, dental, and vision coverage
- Catered lunches (Pittsburgh office)
- Flexible work arrangements
- Visa sponsorship available for exceptional candidates\
INTERVIEW PROCESS
🔎 Application Review — We read everything.
🗣 Recruiter Screen — We learn about you; you learn about us.
🧑💻 Hiring Manager Screen — Meet with the hiring manager and dive deeper into your technical recruiting experience.
🗣 Virtual Onsite Interview — Meet members of the team and learn more about how we work.
😇 Reference Checks — We’ll reach out to 3–5 references that you provide.
📃 Offer — If it’s mutual, we move fast.
Requirements
Must-haves
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 role is in-person at our Pittsburgh office, four days per week. We provide relocation support.
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)
Lead high-risk employee matters: investigations, terminations, leave and accommodation cases, agency charges and any reductions in force. Know when to bring in outside counsel
Find and close existing compliance gaps
Lead benefits and HR programs
Own our HRIS, payroll and people platforms. Evaluate whether our current tools will hold up as we grow, choose new ones when needed, and set our people data strategy
Own benefits strategy, plan design and budget. Choose and manage brokers and carriers, and lead renewals
Build a benefits program that stays competitive and compliant (ERISA, COBRA, ACA) as headcount and locations grow, including multi-state and international coverage
Inform compensation
Help shape our compensation philosophy, salary bands and equity guidelines as we scale, using your market knowledge and experience
Make sure pay practices comply with pay transparency and equal pay laws, and run pay equity reviews
Lead the People function
Develop the People and Talent Teams by coaching and growing these functions and building capabilities and structure of People Operations as the company scales
Provide insight and direction on our people programs, from hiring and onboarding to performance reviews, so they can grow with the company, both in person and remote
Nice-to-haves
Experience with international hiring, such as employer of record, visas and global benefits
Experience shaping compensation and equity frameworks at a growing startup
SHRM-SCP or SPHR certification
Application prep
Use the role’s language and application details while tailoring your materials.