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World’s Best Sales Coaches vs AI

📅 March 17, 2026 ⏱️ 32:40 🎤 Sebastian Jimenez, Pat, Pete Marchmont, Chris Masterson, Jamie Dunbar

Chapters

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  • 0:00
    Welcome to the Rilla Ride-Along Royale
  • 2:17
    Meet Rick Co-pilot: AI that learns your coaching
  • 6:06
    Rick Autopilot: coaching that drives itself
  • 7:45
    Man vs. machine: friend or foe?
  • 10:04
    The main event: the human coaches enter
  • 14:10
    The rules: quality of feedback, not just speed
  • 17:57
    The battle begins: AI jumps to an early lead
  • 24:25
    Team Human uses the co-pilot to close the gap
  • 30:35
    The finish: humanity takes the lead
  • 31:06
    The future of coaching is collaboration (Co-Pilot)

Speakers

Sebastian Jimenez
Sebastian Jimenez
Co-Commentator; CEO & Founder, Rilla
P
Pat
Co-Commentator
P
Pete Marchmont
Sales Coach (Team Human)
C
Chris Masterson
Sales Coach (Team Human)
J
Jamie Dunbar
Sales Coach (Team Human)

Key Takeaways

Rilla staged the first-ever 'Ride-Along Royale,' pitting the world's top human sales coaches against its own AI — Rick Co-pilot and Rick Autopilot — in a live coaching battle.

Virtual ride-alongs give coaches superpowers: reps record their conversations, and the coach reviews and gives feedback in a fraction of the time, so everyone gets coached every day.

Rick Co-pilot learns from your coaching — the more you coach, the better it gets at surfacing coachable moments and drafting feedback in your own voice.

Rick Autopilot goes further, automatically finding the moments you'd have flagged and leaving the feedback itself, like a self-driving car for coaching.

The human edge is transfer of emotion — the sound and conviction of a real coach's voice earned higher-quality ratings from reps than text feedback alone.

The humans surged to take the lead, but Rilla's explicit message was that the future isn't man vs. machine — it's collaboration: coach plus co-pilot.

AI is a 'bicycle for the mind' for coaching — it amplifies great coaches rather than replacing them.

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