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The Great Sales Divide Is Coming. Which Side Are You On?

Over the next 24 months, sales won’t just evolve, it’ll transform. The sellers who master AI will move faster, win bigger, and pull away from the pack.

Author

Matt Greene
April 18, 2025

The Pivot

The AI x Sales deep dive. Where we break down frameworks, tools, and systems to help you move smarter and faster through the enterprise deal cycle.

AI isn’t coming for your sales job. It’s coming for the way you sell. If you believe great sales can only be done by humans, you’re right. But if you’re not rethinking how AI can make those humans ridiculously effective, you’re already behind.

Over the next 12-24 months, we’re going to see something stark - a split between sellers who evolve and sellers who stall. One group is adapting and learning how to leverage AI, rethink workflows, compress cycles, and drive momentum like operators. The other group is clinging to playbooks built for years past. The gap between them won’t just be skill, it’ll be speed, pipeline velocity, forecast accuracy, deal control, and overall productivity.

In short: one group will scale, the other will survive (for a while).

I should caveat this all by saying that my thought has always been, “no way in hell AI will take a sales job.” I actually believe it is one of the most safeguarded jobs there is. Why do I believe that? Because in every big purchase I’ve ever made, the human element really mattered. While I (almost always) do my own research, I also want someone to walk me through the options. I want them to share their take on why it’s worth it, challenge my thinking, negotiate a deal, and ultimately shake my hand when it’s done. I’m also not afraid to admit that I want them to tell my why I should buy it, so I can create my own validation loop. That back-and-forth builds trust.

I don’t think I’m unique in that. Most of us want a human on the other end, especially when we’re buying something that matters. A golf club. A car. A house. A life insurance policy. Even a Facebook Marketplace sofa. Many decisions just aren’t made with a click.

I’ve led many enterprise deals north of $1M. These closed because a human built trust, managed the deal chaos, and drove momentum through dozens of micro-moments that shaped the end result. That’s why I’ve never bought the “AI will replace reps” narrative, but I do believe AI will separate the sellers who scale from the ones who stall. And that change is happening fast.

No matter the company or size of prize, each deal has more the less the same stages. I felt it was helpful to level set on these stages and then begin my journey around applying AI to each step in an A|B tested capacity.

If properly applied, AI can:

A. Increase the probability of advancing to the next deal stage.

B. Create efficiency and timeliness of that stage.

C. Improve forecasting ability (to predictably scale the business overall).

D. Improve overall win rate.

The below is a quick mindmap that shows you the MASSIVE opportunity for AI at every corner of the deal. Once you think of AI as an augmentation at a micro-step, not a replacement, it becomes much more satiable.

Still don’t believe me that AI can enhance each step?

This newsletter is for sales leaders and high-agency reps who want to compress cycles without killing the human element, use AI to sharpen performance - not replace people- and build systems that scale trust, momentum, and precision at every stage of the deal.

We’re not chasing the AI hype cycle, but instead breaking down real applications across the entire sales motion - what works, what doesn’t, and how to use it with intent.

The Locker Room

Let’s be honest - most 1:1s with your manager feel like a pop quiz on your own pipeline.
So instead of walking in cold, read this section and then spend 15 minutes talking sports that you pretend you watched. I’ll give you a sharp take or two and a few relevant insights to break the ice and even a smart comment to say. Then once you’re done talking sports, best of luck on that forecast review.

Jokić Is Redefining Basketball

Headline:
Nikola Jokić became the first center in NBA history to average a triple-double for a full season. Somehow, we’re still asking if he’s the MVP.

Quick Points:

  • The Joker joins Oscar Robertson and Russell Westbrook as the only players to ever average a triple-double

  • 2024–25 season: 29.8 points, 12.8 rebounds, 10.2 assists, 42.4 efficiency rating

  • Recorded a 30-20-20 game (first ever) and a 61-point triple-double

  • Became the fastest player to reach 15K points, 7.5K rebounds, and 5K assists

  • Ranked top 10 in nearly every major statistical category, including steals

What to Say to Your Boss in Your 1x1:
“If we’re talking about what elite actually looks like, start with Jokić. He averaged nearly 30/13/10 across 69 games, led the league in PER (efficiency rating), and made NBA history with a 30-20-20 game. He’s a 7-footer running the offense like a point guard and hitting career milestones faster than anyone in league history. If that’s not MVP, what is?”

Also, this video is awesome.

Rory’s Masters Win Was Built for the Algorithm

Headline:
Rory McIlroy finally won the Masters in his 17th try - completing the career Grand Slam with a finish that felt scripted for social. And the pride of Ireland sure went vira over the weekend.

Quick Points:

  • McIlroy defeated Justin Rose in a sudden-death playoff, sinking a 3-foot birdie putt on the 18th

  • It was his first Masters win, his 5th major title, and his first since 2014

  • The win completed the career Grand Slam, a feat only five other golfers have achieved (Nicklaus, Woods, Hogan, Player, Sarazen)

  • Viral moment: Fans used AI face-swap tools to insert themselves into Rory’s iconic walk up 18

  • PGA Tour highlight clips hit 800K+ views; TikToks with face-swaps drove a trend that merged nostalgia, tech, and fandom

  • McIlroy collapsed in tears after the putt, later saying it was “14 years of pent-up emotion finally released”

  • I still really miss Tiger Woods

What to Say to Your Boss in Your 1x1:
"Rory winning the Masters wasn’t just a comeback. It was closure - 17 tries, 11 years since his last major, and he finally gets the green jacket. First European to complete the Grand Slam. Then it breaks the internet because fans deepfaked themselves into his 18th-hole walk. What a Sunday!"

@golfoncbs

A walk Rory will never forget. #themasters

NIL Just Had Its First Free Agency Meltdown

Headline:
Tennessee QB Nico Iamaleava transferred to UCLA after a failed $4M NIL renegotiation attempt. The message is clear: college football is officially a talent market.

Quick Points:

  • Iamaleava entered the transfer portal April 16, 2025, after Tennessee refused to restructure his $2.4M/year NIL deal

  • He’s expected to join UCLA for less money, likely under $2M

  • His reps demanded $4M for 2025; when the deal fell apart, he missed team meetings and was benched before the spring game

  • The move drew widespread criticism - analysts blamed poor advising, and fans compared his camp’s handling to an unregulated contract standoff

  • His departure leaves Tennessee without their playoff QB and highlights how collectives now function as GMs in a no-rules ecosystem

  • Iamaleava’s original NIL deal ($8M total) helped set national precedent; now his transfer is being framed as a cautionary tale

  • The NIL is an absolute mess, if you ask me

What to Say to Your Boss in Your 1x1:
“Nico tried to jump from $2.4M to $4M after leading Tennessee to the playoff, and the school called his bluff. Now he’s heading to UCLA for less, and the story became a PR disaster. This isn’t about college football anymore - it’s a zero-structure market where players are negotiating like pro athletes without the contracts or the agents. NIL’s not broken. It was never built.”

The NFL Draft Is the Offseason’s Super Bowl

Headline:
The 2025 NFL Draft is about more than who gets picked—it’s about how the league builds momentum, markets future stars, and turns April into a $100M spectacle.

Quick Points:

  • April 24–26 in Green Bay (first time hosting)

  • 200K+ fans expected; local impact projected at $100M+

  • Cam Ward (QB, Miami), Travis Hunter (CB/WR, Colorado), and Abdul Carter (EDGE, Penn State) headline 17 attendees

  • Shedeur Sanders sitting out the event, but still mocked in the top 10

  • Titans hold the No. 1 pick; Eagles pick last at No. 32

  • Dolphins are exploring a Jalen Ramsey trade ahead of the draft

  • NFL Draft Experience features player meetups, contests, and regional food

  • The RB class is stacked; Jeanty (Boise State) could go top 5 - a rarity at the position

  • No first-round trades yet, but movement is expected on draft night

What to Say to Your Boss in Your 1x1:
“The NFL turns a three-day draft into a $100M weekend, controls every media cycle for a week, and sells the future before it’s even on the field. The QB-needy franchises are holding their cards close because the top class is thinner than it looks and Sanders may free fall.”

Singles and Doubles

Other things I found helpful, smart and witty.

Man, this resonates.

A genius ChatGPT prompt:

My new favorite X follow and best post of the year:

I’m Matt

I lead an enterprise sales team, close seven-figure deals, build repeatable go-to-market systems and still make it home for bedtime bottles. I started this newsletter because I believe sales and sport are the same game, and I’m here to show you how to play both better.

Great sellers don’t just push harder. Like great athletes, they find leverage—the fulcrum that moves the outcome. The future belongs to those who move with precision, think like operators, and use AI as a strategic edge.

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