Outside Sales Talk — AI, Automation, and the Future of Sales: What Works (and What Doesn’t)

Host: Steve Benson
Guest: Bill Rice
Date: June 18, 2025

Episode Overview

This episode dives deep into how artificial intelligence (AI) and automation are reshaping outside sales. Bill Rice, founder of Kalydeco and Bill Rice Strategy Group, shares hands-on tactics and insights for outside sales professionals looking to leverage these new tools. From supercharging productivity with AI-powered follow-up emails to the potential pitfalls of over-automation, Bill and Steve discuss what works, what doesn’t, and how sales reps can future-proof their skillsets.

Key Discussion Points & Insights

1. Where AI Fits Best in the Sales Process

• Efficient Communication: The easiest “on-ramp” for sales reps is using AI tools like ChatGPT, Gemini, and Claude to draft efficient follow-up emails and email sequences.
  • Quote [02:45]:

    "I think probably the easiest or the lowest hanging fruit ... is just simply making more efficient some of your communications ... just allowing you to communicate better, putting out a prompt into ChatGPT, asking for it to help you write a follow up email..."
    (Bill Rice)

• Embedded AI in Everyday Tools: Most sales software now incorporates AI, sometimes invisibly, such as suggesting customers to add to a sales route or auto-completing emails.
  • Quote [06:13]:

    "You might not even know you’re using it ... a lot of software ... just shows up in your life and is useful."
    (Steve Benson)

• Predictive AI: Beyond text generation, AI is being used to predict lead scoring and prioritize sales activities by analyzing CRM and operational sales data.
  • Quote [07:09]:

    "Predictive AI ... is already starting to kind of work its way into the system."
    (Bill Rice)

2. AI as a Personal Sales Assistant

• Automating Routine Tasks: Bill advocates automating operational tasks (lead scoring, nurturing) to free up salespeople for high-value human interactions—sales calls, demos, and discovery.
  • Quote [11:49]:

    "We should have automation and technology work leads, and we should have people talking to people."
    (Bill Rice)

• Sales Call Analysis: AI can review call transcripts, provide coaching feedback, and highlight missed opportunities post-call.
  • Quote [12:32]:

    "After every sales call, I ask [AI] to review and analyze the call ... Probably the most important is part of that prompt asks ... what did I miss?"
    (Bill Rice)

• Follow-Up Email Generation: Automate prompt, personalized follow-up emails to increase conversion rates and responsiveness.
  • Quote [00:00, repeated at 13:47]:

    "I have [AI] write a follow up email that gives me key takeaways and specific next steps ... it gives just a beautiful email that tells that client, ‘hey, I enjoyed talking with you. Here's some of the things specifically we talked about ... here's what I think we should do next’..."
    (Bill Rice)

3. AI, Lead Scoring, and Predicting Buyer Readiness

• Overcoming Gut Instinct Bias: AI predictive models often find key signals for deal success that humans overlook.
  • Quote [16:09]:

    "There's this common misperception that ... we weight certain characteristics and ... we’re rating it based on the desirability of that lead ... but what the actuality is ... you might find smaller organizations have less decision constraints ... and you can turn more of those into closings quicker."
    (Bill Rice)

• Intent vs. Activity: AI reveals that buyer intent, not rep activity, is more predictive of closing.
  • Quote [18:56]:

    "Their intent is far outweighs anything we do in order to be ... persuasive ... so a lot of times that intent comes through some features of that lead."
    (Bill Rice)

4. Relationships, Risks, and the Limits of Automation

• Improving Responsiveness Without Losing Authenticity: Automating mundane tasks increases overall responsiveness and leaves more time for relationship-building.
  • Quote [20:36]:

    "If we can automate some of the more mundane tasks ... the actual relationship improves ... but ... we have to be careful not to fall victim to trying to get AI to do our homework."
    (Bill Rice)

• Risks of Over-Automation: Overusing personalization or automating too much can decrease credibility and trust. Recipients notice repeated, impersonal gimmicks (e.g., referencing a local coffee shop, old LinkedIn info).
  • Quote [24:24]:

    "When we try to overly rely on things like personalization, ... AI could potentially cause the same awkward interactions and immediate trust and credibility traps that just kill anything further..."
    (Bill Rice)

  • Quote [25:22]:

    "Half the time it’s not even a mistake. They are correct, that is a good coffee shop, but ... the gimmick is tired."
    (Steve Benson)

5. Enhancing Customer Experience with AI

• Qualifying and Filtering: AI can help sort and qualify leads, ensuring prospects don’t waste time if there’s no fit.
  • Quote [26:14]:

    "Sales is a sort of a sorting and filtering exercise and I think AI can help with that ... being able to use AI initially to work through that..."
    (Bill Rice)

• Intentional and Relevant Communication: Use AI to build relevant sequences, keep prospects engaged, and provide timely, value-added follow-ups.

6. Adapting for the Future: Sales Skills in the AI Era

• Embrace, Don’t Fear AI: The best salespeople will be those who skillfully use AI, not those replaced by it.
  • Quote [31:55]:

    "AI won’t replace you, but someone who is really good at AI will replace you."
    (Bill Rice)

• Conversational Skills: Salespeople’s ability to chat and ask questions translates perfectly to leveraging large language models (LLMs).
  • Quote [32:25]:

    "The user interface for all of them are chat windows ... to be really good at it is to get really good at chatting."
    (Bill Rice)

• No Technical Barriers: Non-technical users often get more value from LLMs because they approach them conversationally.

7. Practical AI Tool Stack for Salespeople

• Recommended Tools:
  • ChatGPT: Best all-purpose starting point for conversations, writing, and feedback.
  • Perplexity: Deeper research and document synthesis.
  • Google NotebookLM: Best for deep-dive analysis on transcripts or uploaded content; acts as a sales director/coach.
  • Example Use [38:25]:

    "Perplexity is great for deep research. Notebook LM ... for analyzing my sales transcripts ... I use it like a sales director or like a sales coach ... give me feedback in aggregate across all of those transcripts."
    (Bill Rice)

Notable Quotes & Memorable Moments

• [00:00] Bill Rice: "I have it write a follow up email that gives me key takeaways and specific next steps...it gives just a beautiful email..."
• [11:49] Bill Rice: "Automation and technology work leads, and we should have people talking to people."
• [16:09] Bill Rice: "Lead scoring ... actually the consumer or the prospect, their intent far outweighs anything that we do in order to be sort of persistent or persuasive."
• [20:36] Bill Rice: "If we can automate some of the more mundane tasks ... the actual relationship improves ... but ... we have to be careful not to fall victim to trying to get AI to do our homework."
• [24:24] Bill Rice: "Over-reliance on automation causes awkward interactions and credibility traps."
• [31:55] Bill Rice: "AI won't replace you, but someone who is really good at AI will replace you."
• [32:25] Bill Rice: "Never start with a blank sheet of paper ... have a conversation with AI."
• [41:15] Bill Rice: "The biggest misperception is sitting there with anxiety over the fact that I need to be technical to use this tool, and that's absolutely not the case."
• [42:22] Bill Rice: "The fact now that we can literally [send follow-ups] within 30 minutes after the call ... you give that wow experience..."

Timestamps for Major Segments

• [02:45] — How AI and automation boost productivity in outside sales
• [06:00-09:00] — AI becoming invisible in everyday sales tools
• [11:49] — Human vs. machine: What should be automated and what needs a personal touch
• [12:30-14:30] — Practical methods for post-call analysis and email follow-up
• [16:09-20:16] — Predictive lead scoring: Truths and misconceptions
• [20:36-25:53] — The double-edged sword: Relationship impact and risks of over-automation
• [26:14-30:00] — Using AI to filter prospects and personalize the customer journey
• [31:55-36:46] — The evolving skillset: Conversation as the new “coding” skill
• [37:58-40:10] — Tool stack recommendations: Practical applications of ChatGPT, Perplexity, NotebookLM
• [41:15-42:22] — Overcoming AI misconceptions and quick tips to outpace the competition
• [45:36-48:54] — AI hacks: Customizing resumes, cover letters, and other “little annoying tasks”
• [48:54] — Actionable first step: Pick a tool, pay for premium, and build your AI habit

Conclusion & Immediate Takeaways

• Start experimenting with AI in your daily workflow, especially for tasks like follow-up emails and call analysis.
• Don’t over-automate—let AI handle repetitive work, but keep your personal touch in every customer conversation.
• Lead with productivity and quality: Respond quickly and with higher-quality deliverables using AI as your assistant.
• Pick a tool (e.g., ChatGPT paid version), keep it open, and use it throughout your day—even small usages add up to big wins in responsiveness and quality.
• Build your skillset for the future: Salespeople who master AI will have a huge advantage.

How to Reach Bill Rice & Additional Resources

• Newsletter: myexecutivebrief.com – Curation and original content on sales, AI, and strategy.
• YouTube: Bill’s growing, active channel (linked from newsletter).
• Free Resources: billricestrategy.com/resources – 90-day sales plan, templates, etc.
• LinkedIn: Bill Rice – active and responsive, great for direct connection.

This summary captures all essential guidance, insights, and practical tips from the episode, enabling you to implement AI and automation efficiently in your sales process—without losing the human edge.