Head of Legal, Compliance

GreenLight.ai

. Lead GreenLight’s legal and compliance function as a hands-on member of the leadership team .

Posted 10/13/2026full-timeRemote • United StatesLeadWebsite

Core Competencies

Role fit

Core Competencies

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Demonstrates extensive expertise in US Employment Law and Workforce Compliance, with a strong ability to translate complex legal requirements into practical business solutions and scalable processes. Proven experience in managing legal standards, compliance frameworks, and international legal coordination while effectively influencing stakeholders.

Highest-signal resume keywords

US Employment Law ExpertiseWorkforce Compliance ManagementLegal Negotiation SkillsAI and Legal Technology ProficiencyIn-House Legal Experience

ATS Keywords

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Applicant Tracking System Keywords

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Hard Skills

Employment LawWorkforce ComplianceLegal Standards OversightContract NegotiationCompliance Process ImplementationWorker ClassificationAudit Process DevelopmentRegulatory MonitoringInternational Legal CoordinationLegal Research

Soft Skills

Influencing ColleaguesClear CommunicationProblem SolvingPublic SpeakingTime Management

Tools & Technologies

Legal TechnologyAI-Enabled Compliance FeaturesKnowledge Management Systems

Certifications & Qualifications

JD or Equivalent Law DegreeActive Membership in US State Bar

Industry Keywords

EOR ServicesAOR ServicesContingent Workforce ProgramsTalent MarketplacesWorkforce Technology

About the role

Key responsibilities & impact

Lead GreenLight’s legal and compliance function as a hands-on member of the leadership team
Protect the business, support growth, and turn complex workforce regulations into practical decisions, scalable processes, and product capabilities
Work directly with the CEO and partner with product, engineering, HR, payroll, operations, and commercial teams
Own legal standards and compliance oversight
Support functional leaders in implementing legal and compliance standards
Manage US and international outside counsel
Own the compliance framework for EOR, AOR, and independent contractor engagements, including worker classification, wage and hour, exempt status, and co-employment risk
Establish policies, controls, escalation routes, and audit processes
Oversee classification assessments, quality review, reassessment triggers, and decision records
Train relevant teams and develop practical guidance for clients and workers
Translate regulatory requirements into classification rules, onboarding controls, workflows, and audit trails
Partner with product and engineering on AI-enabled compliance features, including validation, explainability, and human review
Draft and negotiate client, vendor, worker, and international partner agreements
Develop templates and negotiation guidance for efficient contracting and appropriate risk, liability, and indemnity allocation
Coordinate global compliance with local counsel and partners, including country requirements, licensing, and engagement restrictions
Strengthen partner diligence and oversight as international business grows
Select and coordinate US and international legal specialists, set priorities and service expectations, manage legal spend, and turn advice into business decisions and operational actions
Advise HR and delivery teams on significant employee relations matters, disputes, claims, and investigations
Coordinate responses with outside counsel and relevant insurers
Partner with operations and technology on worker identity, fraud prevention, workforce data privacy, and responsible AI use
Monitor regulatory developments and ensure relevant changes reach policies, platform, and operating processes
Use AI and legal technology to improve research, contracting, and knowledge management with verification and confidentiality controls
Support enterprise diligence, client presentations, selected webinars, and industry events
Review external claims and help develop accurate compliance content
Establish a prioritized compliance roadmap, strengthen classification and international partner controls, improve enterprise contracting, and make regulatory updates actionable across the platform and operations
Participate in a short practical case exercise during the assessment process

Requirements

What you’ll need

Typically 8 or more years in employment law, workforce compliance, and related commercial matters, with substantial responsibility for practical business advice; exceptional candidates with less experience will be considered
JD or equivalent law degree
Active membership in good standing with a US state bar
Deep knowledge of US employment law and worker classification, including complex multi-state workforces
Experience coordinating international legal advice
Evidence of negotiating business agreements
Experience implementing compliance processes
Ability to make clear, proportionate recommendations under time pressure
Ability to translate legal requirements into product and workflow changes
Practical experience using AI or legal technology and evaluating its outputs
Ability to manage outside counsel
Ability to influence colleagues and explain complex issues clearly to enterprise clients and hiring managers
Willingness to develop a credible public voice in workforce compliance
Builder mentality: identify gaps, recommend solutions, and actively implement improvements
Experience in staffing, EOR/AOR services, contingent workforce programs, talent marketplaces, or workforce technology is particularly valuable
In-house experience and experience building a legal or compliance function are strong advantages
Legal right to work in the location applied for without requiring visa sponsorship now or in the future

Benefits

Comp & perks

Flexible working arrangements
Benefits
Home office stipend
Direct access to the CEO
Meaningful voice in product and business decisions
Opportunity to shape how leading organizations manage their extended workforce