Head of Legal, Compliance

This is a fully remote position, open to applicants in United States.

📋 Description

• Take the lead in GreenLight’s legal and compliance functions as a proactive member of the leadership team.

• Safeguard the business, facilitate growth, and convert intricate workforce regulations into actionable decisions, scalable processes, and product functionalities.

• Collaborate closely with the CEO and work in partnership with product, engineering, HR, payroll, operations, and commercial teams.

• Maintain ownership of legal standards and compliance oversight.

• Assist functional leaders in executing legal and compliance standards.

• Manage both US and international external counsel.

• Oversee the compliance framework for EOR, AOR, and independent contractor engagements, addressing worker classification, wage and hour issues, exempt status, and co-employment risks.

• Establish policies, controls, escalation processes, and audit procedures.

• Supervise classification assessments, quality reviews, reassessment triggers, and decision documentation.

• Provide training to relevant teams and create practical guidance for clients and workers.

• Convert regulatory requirements into classification rules, onboarding controls, workflows, and audit trails.

• Collaborate with product and engineering on AI-driven compliance features, including validation, explainability, and human oversight.

• Draft and negotiate agreements with clients, vendors, workers, and international partners.

• Create templates and negotiation guidelines for efficient contracting, while ensuring proper risk, liability, and indemnity distribution.

• Coordinate global compliance efforts with local counsel and partners, addressing country-specific requirements, licensing, and engagement limitations.

• Enhance partner diligence and oversight as the international business expands.

• Select and manage US and international legal specialists, establish priorities and service expectations, oversee legal expenditures, and transform legal advice into business decisions and operational actions.

• Advise HR and delivery teams on critical employee relations issues, disputes, claims, and investigations.

• Coordinate responses with external counsel and relevant insurers.

• Collaborate with operations and technology on worker identity, fraud prevention, workforce data privacy, and responsible AI utilization.

• Keep track of regulatory changes and ensure that relevant updates are reflected in policies, platform, and operational processes.

• Leverage AI and legal technology to enhance research, contracting, and knowledge management, ensuring verification and confidentiality controls.

• Assist in enterprise diligence, client presentations, selected webinars, and industry events.

• Review external claims and contribute to the development of accurate compliance content.

• Create a prioritized compliance roadmap, strengthen classification and international partner controls, enhance enterprise contracting, and ensure regulatory updates are actionable across the platform and operations.

• Participate in a brief practical case exercise during the assessment process.

⛳️ Requirements

• Typically requires 8 or more years of experience in employment law, workforce compliance, and related commercial matters, with significant responsibility for providing practical business advice; exceptional candidates with less experience may be considered.

• JD or an equivalent law degree is required.

• Active membership in good standing with a US state bar is mandatory.

• Extensive knowledge of US employment law and worker classification, particularly in complex multi-state workforces.

• Proven experience in coordinating international legal advice.

• Demonstrated ability to negotiate business agreements.

• Experienced in implementing compliance processes.

• Capable of making clear and proportionate recommendations under time constraints.

• Skilled in translating legal requirements into product and workflow modifications.

• Practical experience with AI or legal technology and evaluating its outcomes.

• Competent in managing outside counsel.

• Proficient at influencing colleagues and clearly articulating complex issues to enterprise clients and hiring managers.

• Eagerness to develop a credible public presence in workforce compliance.

• Builder mentality: identify gaps, propose solutions, and actively implement enhancements.

• Experience in staffing, EOR/AOR services, contingent workforce programs, talent marketplaces, or workforce technology is particularly advantageous.

• In-house experience and a background in establishing a legal or compliance function are strong assets.

• Legal eligibility to work in the applied location without necessitating visa sponsorship now or in the future.

🏝️ Benefits

• Flexible working arrangements.

• Comprehensive benefits package.

• Home office stipend provided.

• Direct access to the CEO.

• A significant role in product and business decision-making.

• Opportunity to influence how leading organizations manage their extended workforce.