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Cyndy McCollough
Founder of McCollough Consulting, specializing in the intersection of technology and marketing within law firms. Expert in AI roadmaps and marketing technology.
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Aug 28, 2025
• 44min
Cyndy McCollough on AI Roadmaps for Law Firms, Middle-Out Change and Piloting Wins
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Cyndy McCollough, founder of McCollough Consulting and expert in AI roadmaps for law firms, shares her insights on integrating technology into legal marketing. She emphasizes the importance of starting small with AI pilots to build comfort and measure success. Cyndy advocates for a middle-out approach to foster collaboration, contrasting it with traditional models. She provides practical tips on tools like prompt libraries and email triage, enabling teams to focus on high-value work, drawing on her rich experience from the tech giants Microsoft and Oracle.
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