Hayley Abolafia-Cartwright serves as Director of Experience across LeadAI Legal® and GenCo Legal®, where she leads the client and partner experience behind the firm’s AI governance work. Working alongside Founder and AI Governance Attorney Bryan Rotella, she brings clarity, coordination, and continuity to LeadAI Legal’s engagements. She ensures clients feel supported, priorities stay aligned, and every interaction reflects the firm’s standard of care.

Her role connects relationship strategy, executive coordination, and operational leadership across LeadAI Legal’s four core offerings: the AI Risk Stress Test™ diagnostic, AI’s Rules of the Road™ leadership education, AI Executive Counsel, and AI Litigation Defense. Members of the Executive Counsel engagement also receive regular insights on what happened in AI law and governance, what was not reported, and what is coming next. From first conversation through ongoing engagement, Hayley creates the continuity, responsiveness, and follow-through that allow leadership teams to engage the firm before the governance question arrives.

You will see her on the floor after Bryan’s keynotes, in the conversations that continue afterward, reconnecting with valued relationships and making new ones. Vermont raised her. Healthcare, compliance, and value-based care are the communities she has built in her own right, including at the Texas Association of Accountable Care Organizations and the Florida Association of ACOs.

For boards, general counsel, and senior leaders in regulated healthcare and technology, Hayley ensures that LeadAI Legal’s work is experienced not only as legal counsel, but as a relationship defined by clarity, consistency, and care.

Leadership

Hayley’s background in communications, talent development, and executive strategy has shaped her as a relationship-centered leader. She ensures that every client and collaborator feels understood, prioritized, and supported. Hayley is the primary point of contact for scheduling and collaboration across the firm, coordinating meetings with clients, prospective partners, and event organizers, and creating the follow-through that supports LeadAI Legal’s mission.