Head of Legal & Compliance

Location: United States Workplace: Remote WHO WE ARE GreenLight.ai http://GreenLight.ai provides global, enterprise-grade workforce infrastructure for enterprise contingent workforce programs and talent platforms. We combine Employer of Record (EOR), Agent of Record (AOR), freelancer management (FMS), and intelligent worker classification with technology that connects directly to our clients’ workforce systems. Trusted by some of the world’s most highly recognized and innovative companies, we help clients engage and manage their extended workforce across the US and internationally. Compliance is central to our service, our technology, and the trust our clients place in us. THE OPPORTUNITY You will lead GreenLight’s legal and compliance function and serve as a hands-on member of our leadership team. Your mandate is to protect the business, support growth, and turn complex workforce regulations into practical decisions, scalable processes, and product capabilities. You will work directly with the CEO and partner with product, engineering, HR, payroll, operations, and commercial teams. You will own legal standards and compliance oversight, support functional leaders in implementing them, and manage our US and international outside counsel. This role combines deep workforce expertise with commercial judgment and the ability to build systems that scale. WHAT YOU WILL DO - Lead workforce compliance. Own our compliance framework for EOR, AOR, and independent contractor engagements, including worker classification, wage and hour, exempt status, and co-employment risk. Establish clear policies, controls, escalation routes, and audit processes. - Strengthen classification. Oversee classification assessments, quality review, reassessment triggers, and decision records. Train relevant teams and develop practical guidance for clients and workers. - Shape the product. 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. - Manage commercial legal work. Draft and negotiate client, vendor, worker, and international partner agreements. Develop templates and negotiation guidance that support efficient contracting and appropriate allocation of risk, liability, and indemnities. - Coordinate global compliance. Work with local counsel and partners to assess country requirements, licensing, and engagement restrictions. Strengthen partner diligence and oversight as our international business grows. - Manage outside counsel. Select and coordinate US and international specialists, set priorities and service expectations, manage legal spend, and turn their advice into clear business decisions and operational actions. - Handle material legal escalations. Advise HR and delivery teams on significant employee relations matters, disputes, claims, and investigations. Coordinate responses with outside counsel and relevant insurers. - Build broader compliance controls. Partner with operations and technology on worker identity, fraud prevention, workforce data privacy, and responsible AI use, drawing on specialist advice where needed. - Make legal knowledge actionable. Monitor regulatory developments and ensure relevant changes reach our policies, platform, and operating processes. Use AI and legal technology to improve research, contracting, and knowledge management, with verification and confidentiality controls. - Represent GreenLight credibly. Support enterprise diligence, client presentations, and selected webinars and industry events. Review external claims and help develop useful, accurate compliance content. WHAT YOU BRING - Relevant legal experience. Typically 8 or more years in employment law, workforce compliance, and related commercial matters, with substantial responsibility for practical business advice. We will consider exceptional candidates with less experience. - Legal qualifications. A JD or equivalent law degree and active membership in good standing with a US state bar. - Workforce expertise. Deep knowledge of US employment law and worker classification, including complex multi-state workforces, and experience coordinating international legal advice. - Commercial and operational judgment. Evidence of negotiating business agreements, implementing compliance processes, and making clear, proportionate recommendations under time pressure. - Technology fluency. Ability to translate legal requirements into product and workflow changes, plus practical experience using AI or legal technology and evaluating its outputs. - Leadership and communication. 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 play an active part in implementing 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. WHAT SUCCESS LOOKS LIKE In your first year, you will establish a prioritized compliance roadmap, strengthen classification and international partner controls, improve enterprise contracting, and make regulatory updates actionable across our platform and operations. Teams will understand their responsibilities and know when and how to escalate material risks. WHY JOIN GREENLIGHT You will have direct access to the CEO, a meaningful voice in product and business decisions, and the opportunity to shape how leading organizations manage their extended workforce. We offer flexible working arrangements, benefits, and a home office stipend. HOW WE WILL ASSESS CANDIDATES We will focus on demonstrated judgment and results: how you have resolved difficult workforce issues, improved processes, managed counsel, and helped a business move forward responsibly. Our process will include discussion of your experience and a short practical case exercise.