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24
Midnight
To Millions
24 Hours. 24 Experts. 0 Excuses.
The AI Fluent Sales Org: Strategy, Skill, and Scale
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Show Notes

Build an AI-fluent sales team that moves faster, thinks sharper, and sells smarter. This session covers the SAIL framework for AI fluency: build core Skills like prompting with a clear gift (goal, audience, desired output, tone), Amplify your unique human strengths with weekly “test and tweak” habits, integrate AI across the full funnel from social proof to evangelism, and lead with leadership that looks around corners and sets simple, repeatable rhythms. 

You learn to triangulate inputs (industry, company, person) so AI produces relevant insights, simplify outputs to third-grade readability for higher response rates, segment enablement by rep skill levels, and add a 5-minute “teach the team one AI thing” round robin to every weekly meeting. 

The result is a practical operating system where AI drafts and routes, humans add judgment, and managers scale excellence through habits instead of one-off hacks.

Main Takeaways

  • Prompt with purpose by packaging a clear goal, specific audience context, defined output, and tone, then triangulate person, company, and industry inputs so messages land.
  • Turn curiosity into a habit with a daily 15-minute “test and tweak” block, a simple Eisenhower clean-up using AI, and a weekly 5-minute peer share that compounds team fluency over time.
  • Operationalize AI across the sales cycle by integrating it into research, messaging, reviews, and social proof while keeping a human in the loop for quality, coaching, and leadership decisions.

Speakers

Cherilynn Castleman
Cherilynn Castleman
Executive Sales Coach
CGI, LLC
Marcus Chan
Marcus Chan
CEO
Venli Consulting
Justin Jay Johnson
Justin Jay Johnson
CEO and founder
Software Sales Coach

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How Midnight to Millions Was Created

Midnight to Millions was born from a shared mission: to unite the best minds in sales for something bigger than another webinar.

It’s the brainchild of five of the industry’s most respected thought leaders — Neil Weitzman, Scott Leese, Marcus Chan, Richard Harris, and Justin Jay Johnson — each bringing decades of real-world experience in building, leading, and training sales teams.

Together, they set out to create a 24-hour global experience that cuts through the noise and reignites what sales should be about: authentic conversations, practical strategy, and world-class community.