Head of Legal & Compliance

Overview

This role leads the organization’s legal and compliance function and serves as a hands-on member of the leadership team. The 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. Responsibilities include owning legal standards and compliance oversight, supporting functional leaders in implementing them, and managing US and international outside counsel.

Responsibilities

• Lead workforce compliance

  • Own the compliance framework for Employer of Record (EOR), Agent of Record (AOR), and independent contractor engagements.
  • Cover worker classification, wage and hour, exempt status, and co-employment risk.
  • Establish 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 product compliance capabilities

  • 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 to 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 the international business grows.

• Manage outside counsel

  • Select and coordinate US and international specialists.
  • Set priorities and service expectations, manage legal spend, and convert 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.
  • Use specialist advice where needed.

• Make legal knowledge actionable

  • 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.

• Represent credibly in enterprise diligence

  • Support enterprise diligence, client presentations, and selected webinars and industry events.
  • Review external claims and help develop 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.
  • Exceptional candidates with less experience will be considered.

• Legal qualifications

  • 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.
  • Experience coordinating international legal advice.

• Commercial and operational judgment

  • Demonstrated ability to negotiate business agreements, implement compliance processes, and provide clear, proportionate recommendations under time pressure.

• Technology fluency

  • Ability to translate legal requirements into product and workflow changes.
  • Practical experience using AI or legal technology and evaluating its outputs.

• Leadership and communication

  • Ability to manage outside counsel, influence colleagues, and clearly explain complex issues 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.

• Additional experience (preferred)

  • 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.

What success looks like

In the first year, success includes:

• Establishing a prioritized compliance roadmap
• Strengthening classification and international partner controls
• Improving enterprise contracting
• Making regulatory updates actionable across the platform and operations
• Ensuring teams understand responsibilities and know when and how to escalate material risks

Compensation & Benefits

• Flexible working arrangements
• Benefits
• Home office stipend

Location

Flexible working arrangements are offered; home office stipend provided.

How candidates are assessed

Focus is on demonstrated judgment and results, including how you have:

• Resolved difficult workforce issues
• Improved processes
• Managed counsel
• Helped a business move forward responsibly

The process includes a discussion of your experience and a short practical case exercise.