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Nothing Kills Quota Like Chasing the Wrong Buyer

Your pipeline looks full, yet deals crawl toward quarter-end. Deep down you wonder: are you even talking to people who care?

Author

Matt Greene
May 17, 2025

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The Pivot

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

Prospects rarely admit, “We’re not your audience.” Instead, they nod, ask for another deck, then vanish. Weeks later the “circle back next fiscal” email hits your inbox and the sobering reality that you’ve wasted time, energy and resources on a deal you would never win. Why? Because you were targeting the wrong ICP (short for ‘ideal customer profile’). 

While product marketers may own the early stages of creating an ICP for your company, it is imperative for the sales rep to know their ICP better than they know their own name, and on the sales manager to continue to refine it as you spend more time in market. Don’t be fooled, this exercise is harder than you might think and the attention to the detail really matters. Which is exactly why we’re going to use AI to help you out.

Step 1: Leverage your CRM tool. I created a data dump of ALL our closed deals in the last 2 years and put it into a pivot table. This will serve as your reference data that is fed into ChatGPT to analyze. Key components: buyer title, solution type, # of sales, $ of each sale. Etc

Step 2: Creation of a Persona. You will have a lot of similar titles and 'noise' in the input data. That's OK. The goal here is to distill it down into a coherent, manageable list.

You will get an output similar to the following.

Once the initial output has been created, it is time to refine it and optimize it based on whatever criteria makes the most sense to you and your business. Get creative and make sure it is usable for you!

I used very simple prompts to get it to tweak mine. As example…

  • “Now leverage the deal status to corroborate your ICP. Closed/Won means we won the deal. Anything else means we did not. Force rank in descending order based on strongest ICP (meaning they are leading to most deal closures). Add a column that provides their real titles (in aggregate), so I can look for them on linkedin.” 

  • “I need more detail than just 'Generalist Stakeholder.' Thoroughly re-evaluate the buyers who make up this group and re-execute this with more prescribed persona.”

  • “Make the solution match more detailed. I want to know exactly what product I should be selling this person. Also add a column for each persona that is % of dollars closed/won (vs. the aggregate closed won $ amount).”

Now that your buyer personas are stack-ranked and you have good understanding on how to evaluate each prospect, we will now ask ChatGPT to analyze patterns and glean insights from your previous sales activities (data), using this established framework.

Boom. You now have a tailored and critical assessment of how well you (or your team) is selling into their ICP, with recommendations on how to uplift the areas of perceived weakness.

Also, never ask your boss what an ICP is in a public forum. It’s, uhh, table-stakes for selling.

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.

Mavericks Win Draft Lottery for Flagg

Summary:
Dallas’ shock NBA Draft Lottery win secures Cooper Flagg, amplifying their competitive edge and market value.

  • Mavericks had 1.8% odds to land No. 1 pick on May 12 and somehow did it.

  • Flagg, Duke’s top prospect, is a franchise cornerstone and possibly a reason why the GM will keep his job.

  • “This changes our trajectory,” GM Nico Harrison said.

  • This significantly boosts Dallas’ sponsorship revenue and Western Conference leverage.

What to Say to Your Boss in Your Next 1×1:
“Did you see the NBA lottery? Dallas hit the jackpot - a total game-changer! It’s a huge win for their brand and could increase sponsorship revenue by $10–20 million per year! Long-term, Flagg’s ability to anchor a contending team alongside Anthony Davis and Kyrie Irving could elevate the Mavericks’ franchise valuation, potentially exceeding $4 billion!”

Celtics Crush Knicks in Game 5

Summary:
Boston’s dominant Game 5 win over New York keeps their title hopes alive, showcasing resilience despite injuries.

  • Celtics won 127-102 on May 14, forcing Game 6.

  • Derrick White’s 34 points led a 22-of-49 three-point barrage.

  • “We responded to the test,” Mazzulla said.

  • Extends series, shifting momentum and sponsor interest.

What to Say to Your Boss in Your Next 1×1:
“Celtics showed up big in Game 5, winning by 25 points. Their depth kept them alive without Tatum. It’s all about staying power and depth. Let’s talk about how I can build my team like that.”

MLB Reinstates Pete Rose Eligibility

Summary:
MLB’s rule change reinstating Pete Rose’s Hall of Fame eligibility sparks debate over legacy and governance.

  • Rule shift on May 13 lifts Rose’s gambling ban.

  • Decision aligns with evolving sports betting policies.

  • “We’re adapting to reality,” MLB official said.

  • Could increase Hall revenue but risks fanbase division.

  • The Hall’s 2024 revenue was approximately $20 million, and a high-profile figure like Rose could drive a 50 - 75% attendance spike in the induction year, based on historical data from other controversial inductees.

What to Say to Your Boss in Your Next 1×1:
“MLB just opened the door for Pete Rose’s Hall of Fame shot. This could have a big impact to revenue but is definitely going to divide the masses. Induction could increase Cooperstown’s annual revenue by an estimated $15 million through boosted ticket sales, merchandise, and tourism.”

Browns’ Rookie Minicamp Highlights Sanders

Summary:
Shedeur Sanders’ standout performance at the Browns’ rookie minicamp signals his potential to reshape Cleveland’s quarterback strategy.

  • Sanders completed 80% of passes at minicamp on May 12.

  • Browns prioritize Sanders as a draft cornerstone.

  • “He’s a leader,” coach Kevin Stefanski said.

  • Could boost Cleveland’s competitiveness and fanbase revenue.

What to Say to Your Boss in Your Next 1×1:
“Cleveland’s buzzing about Shedeur Sanders. He has hit 80% of passes in minicamp and is the talk of the NFL off-season. Amazing that a 5th round QB is bringing this type of hype.”

Singles and Doubles

Other things I found helpful, smart and witty.

The great Robert Sterling does not miss with his memes, or takes in general.

I’ve found gold through following the God of Prompt. Some of it is practical, some of it is downright scary.

I can picture the exact location my 8th grade bus was when I first heard Stan, via a burned CD, on my Sony walkman. This playlist gives me all the feels.

I’m Matt

I lead a software 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 a similar game, and want you to be better at both. Great sellers don’t just push harder. Like great athletes, we find leverage - the fulcrum that moves the outcome. The future of successful sales belongs to those who move with precision, think like operators, and use AI as a strategic edge to win.

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