Head of Legal, Compliance

🕒 October 13

🇺🇸 United States – Remote

⏰ Full Time

🔴 Lead

⚖️ Legal Counsel / General Counsel

👻 Ghost score 25%

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GreenLight.ai

WebsiteLinkedInAll Job Openings

11 - 50 employees

Founded 2018

💼 Consulting

⚖️ Legal

📦 Logistics

💰 Pre seed on 2020-04

Consulting • Legal • Logistics

GreenLight. ai is a B2B SaaS platform that provides a Freelancer Management System (FMS) to help organizations compliantly hire, onboard, classify, manage, and pay freelancers, contractors, and vendors at scale. It combines core FMS features with Employer of Record (EOR), Agent of Record (AOR), and worker classification services, plus APIs, embedded integrations, and white-label options for enterprises, talent marketplaces, and staffing firms. The product emphasizes compliance, configurable workflows, payroll (bill & pay), reporting, and security to reduce legal risk and streamline extended workforce operations globally.

📋 Description

• 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

• 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

• 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

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