06. Jeff Borovitz ~ Sandler by Selling with Jeff

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Episode Notes

Key moments from this episode

Jeff Borovitz joins Tailwind for a practical conversation about using AI in sales without breaking trust: why transparency matters with AI digital twins, how call recording and AI-generated CRM notes reduce rep admin work, why AI-assisted follow-up should still sound human, how roleplay coaching helps sellers practice before they perform, and why the future belongs to hybrid salespeople who combine fundamentals with faster, smarter tools.

AI-assisted salesAI in outboundSales trainingSales mindsetData-driven sales managementManager visibilitySales activity qualityRevenue team operating rhythmOutbound workflow design

Takeaways

  • AI digital twins can reinforce sales training, but only when sellers are transparent that the content is AI-generated.
  • Call recording and AI summaries can make CRM notes more complete while freeing sellers to focus on the buyer.
  • AI is useful for first drafts, brainstorming, and follow-up support, but sellers still need to edit for context and voice.
  • Roleplay coaching lets reps practice safely before they spend expensive live leads learning through mistakes.
  • Hybrid salespeople combine classic sales fundamentals with AI tools that help them practice more, follow up faster, and execute their cookbook.

Key Moments

  1. 0:02

    AI digital twins and sales trust

    Jeff opens with how he uses an AI digital twin while making the disclosure explicit so it does not break trust.

  2. 1:50

    Turning class recordings into follow-up clips

    Jeff explains how call recordings, Claude prompts, and a digital twin help create 60-second class recap videos for students.

  3. 4:03

    Why undisclosed AI breaks trust

    The conversation turns to AI webinars, deception, and why Jeff would not start client or prospect relationships from anything less than honesty.

  4. 7:19

    AI should augment personal touch

    Jeff argues that companies using AI as a replacement for human touch will struggle, while sellers using AI to become more effective will win.

  5. 7:53

    Call recording and better CRM notes

    Jeff describes using call recording and note takers to improve focus during the call and preserve richer CRM data afterward.

  6. 9:59

    AI-assisted follow-up and brainstorming

    Austin and Jeff discuss using AI to avoid blank-screen follow-up, brainstorm outreach, and pressure-test ideas without sending unedited AI copy.

  7. 11:58

    AI needs human context

    Jeff explains why AI can agree too easily or make strange recommendations without context, making critical human review essential.

  8. 14:01

    Reinforcing sales training between classes

    Jeff shares how AI digital twin reminders help students apply Sandler lessons between classes and come back with real attempts to discuss.

  9. 15:59

    AI roleplay coaching before live calls

    The episode moves into AI roleplay coaching, scored custom scenarios, interview practice, and call rehearsal before sellers perform live.

  10. 17:32

    Practice on AI, not expensive leads

    Jeff explains how recorded real calls and AI scoring expose skill gaps, then compares practicing with AI to practicing on costly sales-qualified leads.

  11. 21:07

    The old playbook is incomplete

    Austin and Jeff discuss the human-in-the-loop question and why classic sales fundamentals still matter more in a noisier AI landscape.

  12. 23:17

    Hybrid salespeople practice more than they perform

    Jeff closes by describing hybrid salespeople who combine fundamentals with AI tools, including roleplay reps inside the weekly cookbook.