Head of People

Gray Swan AI•Pittsburgh, PA

12h•$155,000 - $245,000•Onsite

About The Position

Gray Swan is seeking a Head of People Operations to guide the company through its next growth phase. The ideal candidate will have experience scaling a fast-growing company across multiple states, supporting both in-person and remote teams. This role involves leading the entire People function, including the hiring function and People Operations Manager, and setting the strategic direction for people operations to support future growth. Key impact areas include employment compliance as the company scales and benefits and HR systems strategy to support a larger, distributed workforce. This is a senior leadership position reporting to the VP of Operations, with opportunities for growth based on performance.

Requirements

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.
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 supports business objectives.
Ability to work in person in Pittsburgh.

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.

Responsibilities

Lead employment compliance as the company scales, managing requirements for hiring in new states and countries, including registration, payroll tax, leave, final pay, and pay transparency rules.
Track headcount thresholds and prepare for associated laws (e.g., Title VII, ADA, COBRA, FMLA, ACA, EEO-1, WARN).
Set and review employee classifications (contractor vs. employee, exempt vs. non-exempt).
Own company policies, handbook, required postings, and required reporting (EEO-1, ACA).
Lead high-risk employee matters, including investigations, terminations, leave and accommodation cases, agency charges, and reductions in force, knowing when to involve outside counsel.
Identify and close existing compliance gaps.
Lead benefits and HR programs, owning the HRIS, payroll, and people platforms, and evaluating their scalability.
Develop a people data strategy.
Own benefits strategy, plan design, and budget, including choosing and managing brokers and carriers, and leading renewals.
Build a competitive and compliant benefits program (ERISA, COBRA, ACA) for a growing, multi-state, and potentially international workforce.
Inform compensation strategy, including shaping compensation philosophy, salary bands, and equity guidelines.
Ensure compliance with pay transparency and equal pay laws, and conduct pay equity reviews.
Develop the People and Talent Teams through coaching and building capabilities and structure.
Provide insight and direction on people programs (hiring, onboarding, performance reviews) for in-person and remote growth.
Partner with leadership on headcount planning, org design, and people strategy, advising on people risk.