Head of People

Gray Swan AI•Pittsburgh, PA

20h•Onsite

About The Position

Gray Swan is hiring a Head of People Operations to lead the People function as the company grows. Gray Swan has approximately 50 employees and builds AI model evaluations, real-time threat detection, and adaptive adversarial red-teaming agents. The role leads the hiring function and the People Operations Manager, who handle day-to-day recruiting, onboarding, culture, and employee support. The Head of People sets direction and prepares the organization for growth across multiple states and distributed teams. Key areas of leadership include employment compliance, benefits strategy, HRIS and payroll platforms, compensation, and people programs. The role owns compliance processes and risk management, benefits design and administration, people data strategy, and the development of the People and Talent teams. It partners with company leadership on headcount planning, organizational design, compensation, and people strategy, and reports to the VP of Operations. This is an in-person position at Gray Swan’s Pittsburgh office four days per week. Relocation support is available. Compensation is $155,000–$245,000, plus a performance-based bonus and meaningful equity package.

Requirements

Experience scaling a fast-growing company, ideally in technology, across multiple states and with both in-person and remote employees.
At least 8 years of progressive HR experience.
At least 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 experience with benefits planning, including plan design, brokers and carriers, renewals, budgeting, and multi-state coverage.
Experience choosing and implementing HRIS and payroll platforms.
Experience leading teams responsible for recruiting and people operations.
Sound judgment about when to involve employment counsel and a practical approach to compliance that supports business operations.
Ability to work in person in Pittsburgh.

Nice To Haves

Experience with international hiring, such as employer of record arrangements, visas, and global benefits.
Experience shaping compensation and equity frameworks at a growing startup.
SHRM-SCP or SPHR certification.

Responsibilities

Lead employment compliance as the company expands into new states and countries, including registration, payroll tax, leave, final pay, and pay transparency requirements.
Track headcount thresholds and prepare for associated employment laws and reporting requirements.
Set and review employee and contractor classifications, including exempt and non-exempt classifications.
Own company policies, the employee handbook, required postings, and reporting such as EEO-1 and ACA reporting.
Lead high-risk employee matters, including investigations, terminations, leave and accommodation cases, agency charges, and reductions in force; engage outside counsel when appropriate.
Identify and close existing compliance gaps.
Own the HRIS, payroll, and people platforms; assess current tools, select new tools as needed, and set the people data strategy.
Own benefits strategy, plan design, and budget; select and manage brokers and carriers; and lead renewals.
Build and maintain competitive, compliant benefits programs as headcount and locations grow, including multi-state and international coverage.
Help shape compensation philosophy, salary bands, and equity guidelines using market knowledge and experience.
Ensure pay practices comply with pay transparency and equal pay laws, and conduct pay equity reviews.
Coach and develop the People and Talent teams and build People Operations capabilities and structure as the company scales.
Provide direction on people programs, including hiring, onboarding, and performance reviews, so they can support in-person and remote employees.
Partner with leadership on headcount planning, organizational design, and people strategy, and advise on people risk.