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Hayley
Abolafia-Cartwright

Director of Experience

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Shaping The Experience

Hayley serves as the Director of Experience at LeadAI Legal™, where she integrates client relationships, strategic coordination, and operational excellence into a unified experience that embodies the firm’s mission: helping leaders move from promises to proof in how they govern and trust AI. Working alongside Founder and Managing Partner Bryan Rotella, she leads the firm’s experience architecture, from client onboarding and communications to events, partnerships, and culture design.

The Advantage

At the intersection of human connection and intelligent systems, Hayley ensures every interaction with LeadAI Legal reflects foresight, empathy, and precision. Her leadership bridges traditional executive strategy and modern AI adoption, translating complex initiatives into seamless experiences that strengthen relationships and elevate the firm’s reputation as the nation’s first legal specialization dedicated to AI oversight.

Hayley is the primary point of contact for scheduling and collaboration across the firm, coordinating meetings with clients, prospective partners, and event organizers. She’s energized by connecting with thought leaders, exploring keynote and conference opportunities, and fostering relationships that expand the reach and impact of LeadAI Legal’s mission.

Leadership

Hayley’s background in communications, talent development, and executive strategy has shaped her as a relationship-centered leader who transforms operations into experiences. Known for her strategic warmth and meticulous coordination, she ensures every LeadAI Legal partner, client, and collaborator feels understood, prioritized, and inspired.

Expertise

Client Experience Design & Relationship Strategy

Executive Operations & Strategic Coordination

Event Architecture & Thought Leadership Engagement

Executive Operations & Strategic Coordination

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