Head of People

Gray Swan

. Lead the whole People function, with the hiring function and People Operations Manager reporting to you .

Posted 10/15/2026full-timePittsburgh • Pennsylvania • United StatesLead💰 $155,000 - $245,000 per yearWebsite

Core Competencies

Role fit

Core Competencies

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Demonstrates expertise in leading HR functions, including compliance management, benefits planning, and people strategy development. Proven ability to scale HR operations across multiple states and countries while ensuring adherence to employment laws and regulations.

Highest-signal resume keywords

Progressive HR ExperienceEmployment Compliance ManagementBenefits Planning and DesignHRIS and Payroll ImplementationTeam Leadership in People Operations

ATS Keywords

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Applicant Tracking System Keywords

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Hard Skills

FLSA KnowledgeFMLA KnowledgeADA KnowledgeTitle VII KnowledgeADEA KnowledgeERISA/COBRA KnowledgeACA KnowledgeNLRA KnowledgeWARN KnowledgeBenefits Budgeting

Soft Skills

Good JudgmentCoaching and DevelopmentPractical Approach to Compliance

Tools & Technologies

HRIS PlatformsPayroll PlatformsPeople Platforms

Certifications & Qualifications

SHRM-SCPSPHR

Industry Keywords

Multi-State EmploymentInternational HiringCompensation FrameworksEquity GuidelinesPay Equity Reviews

About the role

Key responsibilities & impact

Lead the whole People function, with the hiring function and People Operations Manager reporting to you
Own employment compliance as the company scales across states and countries
Manage 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 applicable employment laws
Set and review contractor/employee and exempt/non-exempt classifications
Own policies, handbook, required postings and required reporting
Lead high-risk employee matters, including investigations, terminations, leave and accommodation cases, agency charges and reductions in force
Find and close existing compliance gaps
Own HRIS, payroll and people platforms; evaluate, select and implement tools and set the people data strategy
Own benefits strategy, plan design and budget; manage brokers and carriers and lead renewals
Build a competitive and compliant multi-state and international benefits program
Help shape compensation philosophy, salary bands and equity guidelines
Run pay equity reviews and ensure pay practices comply with applicable laws
Develop the People and Talent Teams by coaching and growing the functions
Provide direction on hiring, onboarding, performance reviews and other people programs
Partner with leadership on headcount planning, org design, compensation and people strategy, and advise on people risk

Requirements

What you’ll need

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
Preferred: Experience shaping compensation and equity frameworks at a growing startup
Preferred: SHRM-SCP or SPHR certification

Benefits

Comp & perks

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
Performance-based bonus
Meaningful equity package
Relocation support