Jeff Borovitz on AI Sales Tools, Trust, Digital Twins, and Roleplay Coaching

Episode 6 · Jeff Borovitz, President at Sandler by Selling with Jeff

Published · 27m 57s

About Jeff Borovitz

Jeff Borovitz is President of Sandler by Selling with Jeff, where he helps sellers and sales teams reinforce fundamentals, practice better conversations, and use new tools without losing trust.

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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.

Episode Resource

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.

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  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.

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  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.

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  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.

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  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.

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  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.

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  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.

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  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.

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  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.

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  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.

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  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.

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  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.

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Questions answered in this episode

How can sales teams use AI without losing trust?

AI digital twins can reinforce sales training, but only when sellers are transparent that content is AI-generated. AI is useful for preparation and first drafts, while the seller remains responsible for context, accuracy, and voice.

Where does AI improve sales execution?

Call recording and AI summaries can make CRM notes more complete while freeing sellers to focus on the buyer. Roleplay coaching also lets reps practice safely before they spend expensive live leads learning through mistakes.

What makes a strong hybrid salesperson?

Hybrid salespeople combine classic sales fundamentals with AI tools that help them practice more, follow up faster, and execute their cookbook. The tools support judgment and human communication rather than replacing either one.