Fractional CAIO, Chief AI Officer

Estrin Advisory Partners, a new division of Estrin VIP, is building a nationwide network of fractional executives to work on project-based assignments with law firms and in-house legal departments. The CAIO role involves advising legal organisations on AI strategy, governance frameworks, vendor selection, pilot design, risk and compliance guidance, and change management, all tailored to the specific demands of legal practice.

This is a 1099 independent contractor engagement suited to experienced fractional C-suite leaders who want variety and autonomy while contributing to a growing advisory offering backed by more than three decades of legal recruiting expertise. A law firm background is a strict requirement, as is at least five years of fractional C-suite experience. Strong communication skills and the ability to engage confidently at partner level are essential.

• Advise law firm and in-house legal clients on AI strategy and implementation priorities
• Develop AI roadmaps tailored to legal practice environments
• Lead vendor selection and evaluation processes for AI tools in legal settings
• Design and oversee AI pilot programmes, including risk and compliance considerations
• Guide change management efforts to support AI adoption across legal teams
• Engage stakeholders at partner and leadership level to build alignment on AI initiatives

• Law firm background is mandatory - candidates without this cannot be considered
• Minimum five years of experience operating as a fractional C-suite executive
• Deep knowledge of AI strategy, governance, and implementation in professional services contexts
• Ability to work as a 1099 independent contractor
• Strong communication and stakeholder engagement skills for senior legal audiences

Estrin VIP is a legal staffing and advisory firm with more than 30 years of experience placing senior talent in law firms and corporate legal departments across the United States. Its advisory division, Estrin Advisory Partners, is building a dedicated bench of fractional and interim C-suite executives with deep law firm expertise.