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Salary: USD 155,000 - 245,000 / annual
Gray Swan is hiring a Head of People Operations to lead the People function as the company scales from ~50 employees. Gray Swan evaluates AI models for frontier labs and builds real-time threat detection and adaptive adversarial red teaming agents for enterprises deploying AI.
You will lead the entire People function, with the hiring function and People Operations Manager reporting to you. You'll report to the VP of Operations and partner with leadership on headcount planning, org design, compensation, and people strategy. The role is in-person at the Pittsburgh office, four days per week, with relocation support provided.
Key responsibilities include:
**Compliance & Scaling:** Manage employment compliance as the company expands across states and countries. Track headcount thresholds and prepare for associated legal requirements (Title VII and ADA at 15 employees, COBRA at 20, FMLA and ACA employer mandate at 50, EEO-1 and WARN at 100). Set and review contractor vs. employee and exempt vs. non-exempt classifications. Own policies, handbook, required postings, and reporting (EEO-1, ACA). Lead high-risk employee matters including investigations, terminations, leave and accommodation cases, and reductions in force.
**Benefits & HR Systems:** Own the HRIS, payroll, and people platforms. Evaluate current tools and select new ones as needed. Develop benefits strategy, plan design, and budget. Choose and manage brokers and carriers, lead renewals, and build a competitive, compliant program (ERISA, COBRA, ACA) across multiple states and international locations.
**Compensation:** Help shape compensation philosophy, salary bands, and equity guidelines. Ensure pay practices comply with pay transparency and equal pay laws. Run pay equity reviews.
**People Leadership:** Develop and coach the People and Talent Teams. Provide direction on people programs (hiring, onboarding, performance reviews) for both in-person and remote employees. Partner with leadership on people strategy and risk.
**Requirements:**
- 8+ years of progressive HR experience, including 2+ years leading a people function or team
- Experience scaling a fast-growing company (ideally in tech) across multiple states with both in-person and remote employees
- 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; practical approach where compliance enables business growth
- Able to work in-person in Pittsburgh (relocation support available)
**Preferred:**
- Experience with international hiring (employer of record, visas, global benefits)
- Experience shaping compensation and equity frameworks at a growing startup
- SHRM-SCP or SPHR certification
