Head of Legal & Compliance

Overview

Lead GreenLight's legal and compliance function as a hands-on member of the leadership team, owning workforce compliance standards and managing outside counsel across US and international matters.

What you'll do

• 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, and develop templates and negotiation guidance.
• Work with local counsel and partners to assess country requirements, licensing, and engagement restrictions; strengthen partner diligence and oversight.
• Select and coordinate US and international outside counsel, set priorities and service expectations, and manage legal spend.
• Advise HR and delivery teams on significant employee relations matters, disputes, claims, and investigations, coordinating with outside counsel and 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, the platform, and operating processes.
• Support enterprise diligence, client presentations, selected webinars and industry events, and review external compliance claims.

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).
• A JD or equivalent law degree and 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 and 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, 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 take an active part in implementing improvements.

Nice to have

• Experience in staffing, EOR/AOR services, contingent workforce programs, talent marketplaces, or workforce technology.
• In-house experience and experience building a legal or compliance function.

Details

• Location: United States.
• Flexible working arrangements; home office stipend offered.
• Assessment includes discussion of experience and a short practical case exercise.