By John Barrows | March 28, 2026 | 3 min read
The last mile in AI sales is still yours. AI can research faster, write cleaner, and organize better than most people. The real threat is reps who use it to skip the thinking entirely. Gary Vaynerchuk told me in 2017 that the answer was to beat the last mile. That advice has never been more important.
Back in 2017, I went to Gary Vaynerchuk’s office for one of his 4D sessions.
Small group. Gary’s team walking through how they were building brands and leveraging social. At the end, Gary came in and opened it up for Q&A.
Around that same time, a few reps I had trained at Salesforce reached out to me. They had built an AI tool that could write hyper-personalized emails based on my “Why You Now” framework. I didn’t believe them at first. I asked them to send me an example.
When they did, it caught me off guard. It was better than anything I could have written myself, and it did it in a fraction of the time. This was 2017. Before all the AI hype hit.
That was the first time I had one of those “this changes everything” moments with AI.
So when Gary came in, I asked him about it. I told him I’d just seen a robot write a better email than I could and asked where that left me as a trainer and all of us as sales professionals.
His answer has stuck with me ever since.
“Don’t worry about the tech. You’re not going to beat it. Beat the last mile.”
What the Last Mile in AI Sales Actually Means
I didn’t fully appreciate what Gary meant at the time. I do now.
The tech is always going to get better. It’s going to do the research faster. It’s going to organize information better. It’s going to write cleaner, more structured content than most people can on their own.
We’re not going to win by trying to out-AI AI.
But the last mile should still be ours. The last mile is where you take what AI gives you and make it human. It’s where you apply judgment, context, tone, and experience. It’s where you decide what matters, what doesn’t, and how it should actually land with the person on the other end.
The Rep Who Wanted Perfect Output
I was working with a team recently where I had built prompts for reps to create outbound sequences. The prompts worked. They produced solid outputs based on the frameworks I teach.
But one rep kept coming back frustrated because he couldn’t get the AI output to be perfect.
That’s when I realized I needed to be clearer about something: it’s not supposed to be perfect. And it shouldn’t be. If the output is perfect, then what’s the point of your role in the process?
AI is not the final answer. It’s the starting point.
The problem right now is that too many people are using AI to skip the thinking. They ask it to do the research, write the message, build the sequence, and then send it without ever really engaging with it.
That might work in the short term. But it leads to the same problem we’ve always had in sales: everything starts to sound the same.
What I Tell Sales Students
I was talking to a group of sales students at Bentley recently and told them something that didn’t seem to land at first.
If you walk into an interview today thinking your ability to write a personalized email or make a cold call is your differentiator, you’re already behind.
AI can do those things better and faster than you.
What will separate you is how you use it and what you do after it gives you the answer.
Can you take what it produces and make it better? Can you adjust it based on the situation? Can you add context that only comes from actually understanding the business and the person you’re reaching out to?
That’s the last mile.
It applies to everything: emails, calls, proposals, sequences, presentations. AI can get you 70-80% of the way there, maybe even 90%. But the final 10-20% is where the impact is.
That’s where you earn your value.
The Right Question to Ask
Stop asking: “How do I get AI to do this for me?”
Start asking: “How do I use AI to get me close so I can make this better?”
Use it to speed up your research, structure your thinking, and generate a starting point. But don’t outsource your judgment.
Add your perspective. Adjust the tone. Make it sound like you. Make it relevant to the person you’re reaching out to.
Because until computers start buying from each other, there’s always going to be a human on the other end making the decision. And that human is going to feel the difference.
That difference is the last mile.
Frequently Asked Questions
What is “the last mile” in AI-assisted sales?
The last mile is the final step in any AI-assisted task where a human adds judgment, context, and authenticity. AI can draft the email, build the sequence, or structure the proposal, but the last mile is where you make it sound like you, make it relevant to the specific person, and apply your understanding of the situation.
Should sales reps use AI to write their emails?
Yes, as a starting point, not a final answer. AI-generated outreach that’s sent without human review tends to sound generic. The reps who win use AI to do the research and first draft, then apply their own voice, perspective, and situational knowledge before sending.
What skills do sales reps need in an AI-driven sales environment?
The skills that matter most now: judgment (knowing what to keep and what to change), contextual intelligence (understanding the buyer’s real situation), and authentic communication (adding the human layer AI can’t). The reps who will be replaced are the ones who use AI to skip thinking, not the ones who use it to think faster.
How much of a sales task should AI handle?
AI can reliably get you 70-90% of the way there on most sales tasks: research, sequencing, drafting, structure. The remaining 10-30% is still yours. That final edit, that relevant personal touch, that tone adjustment based on context. That’s where the deal is won or lost.
Corporate and individual training available at learn.jbarrows.com. John offers a 20% referral fee for individual training referrals and 10% for corporate referrals.
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