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Coaches Podcast

World’s Best Sales Coaches vs AI

πŸ“… 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 β€” Rick Co-pilot and Rick Autopilot β€” 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 β€” 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 β€” 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 β€” it's collaboration: coach plus co-pilot.

✦

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

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