Maestro got together with our Sales Hall of Famers to talk about how they use AI in their daily professional lives. Here’s the scoop.
June 25, 2025
Last week, Will Fuentes sat down with Maestro’s Hall of Fame sales professionals and asked them how they use AI in their day-to-day sales practices. He heard quite a range of use cases, opinions, and predictions. The answers spanned the gamut, not only in terms of tools our Hall of Famers use, but also in terms of when in the process they use them. One thing they all had in common? Nothing. Just kidding. All of our favorite sales reps are eager to learn from one another, curious about the evolving ways in which people do sales, and interested in improving their own processes.
Our Hall of Famers know that a meeting doesn’t start when you walk in the conference room, pick up the phone, or connect to Zoom. Before meeting, Matt Butler, a VP of mid-market sales at Finvi, will identify recent interactions with that prospect or client and analyze the deal’s current knowns and unknowns, and even tenor. He uses AI to gather information that helps answer the questions, “What are the risks in the deal? What have we uncovered about [the client]? What’s important to them? What’s not?” Matt also uses AI to create question trees and prep the structure of the call.
Eric Jao, the creator of a new music-production curriculum ELEMENTS, will even ask ChatGPT questions about a prospect, via its voice feature. He also uses ChatGPT’s voice as an educational tool, the way he used to browse YouTube videos to widen his knowledge base on a variety of subjects. “You might use it as a little tutor on the way to and from work. It’s really, really great for that. You just have to give it context…You have to tell it what it needs to be an expert in, and then it gives you really good output.”
During meetings, Liz Schuerman, a VP of sales at MBSi, deploys a tool called Fathom to transcribe and create recaps complete with action items and key takeaways. “Every time I send this to somebody they’re like, ‘Wow! I can’t believe you got meeting notes back to me so quickly.’” Liz has even connected the tool to HubSpot, where it can translate the documents it produces into new tasks.
Joshua Pearson, a managing partner of SynOpSys Group, will also use AI-generated meeting transcripts for some of the less tangible aspects of a client or prospect interaction. “I’ll use it to summarize call transcriptions and see if it picks up… tone and sentiment, things that maybe I missed…” Along these lines, Eric probes AI for factors like “inferred benefits, if there are objections that were either inferred or explicit, what it seems like the prospect’s next steps are going to be, likelihood of purchase…” He has even inserted Maestro’s DRIVE framework into ChatGPT to help guide the tool’s output.
Everyone who’s ever looked for a job knows how difficult it can be to try and predict the right answers to interview questions. Though not guaranteed to get it right, AI might be a way to prep using an approach more customized to the companies you’re aiming for. “When I was interviewing for Goodshuffle,” Danny Mullins, who does indeed now work at Goodshuffle as a sales executive, told us, “I fed in their job description, fed in their website,” then had the GPT act as interviewer.
“In my outreach, personalization wins hand over fist,” said Seth Peters, an enterprise sales executive at TrueML. “It just does. That’s what buyers are going to respond best to, but I can only touch so many folks out there in the network…” Seth and his sales-operations manager have used LeadIQ to this end. To do this, they “feed it a lot of our case studies for our various solutions, the value props from our case studies that we’ve been featuring…” They found that the tool improves as they use it/make edits. “It has the ability for you to link individual Linkedin profiles, URLs, company information specific to a company you’re targeting, and that’s really helped me scale my personalized outreach. I break it down by industry, company-to-company, and it’s just allowed my outbound efforts to be more broad, but also not sacrificing the personalization.”
Like Matt, Charlie Cononie, a senior account executive at SalesIntel, finds it useful to lean on AI for messaging. “I’ve basically switched to do a lot of industry- and persona-based sequencing… [for] prospecting efforts.” And Eric has actually built his own GPT for this exact purpose. He is currently expanding his musical-instruction business, so he’s “…looking for district level folks like superintendents, curriculum directors, that type of thing.” In addition to aggregating information on particular professionals Eric has selected (for example, the size of the school district that person is involved with), the GPT will help generate a “strategy for next steps.”
Matt has started creating AI scorecards. “I’m trying to get it done by stage, in terms of, here’s where I expect us to get data points out of each level of the sales process, and I want to score it differently, based off of something top of the funnel versus something more toward the bottom in kind of a contracting phase…” This helps gives him a quick view into which deals could use some TLC because they are progressing and which could use some SOS.
AI can actually affect pipeline health farther down the line than we can currently see. Joshua believes firmly that salespeople “need to start capturing all of your calls. Get call transcriptions, get video transcriptions, start building all of this data that you can use later or put it into a CRM and analyze deals that have slipped a year ago, two years ago, because of budget or timing, or whatever—you can have AI quickly go through this and identify those things like overnight…”
“We all know gifting, right, from Maestro training?” asked Danny. (He’s referring to a practice Maestro encourages. We define a gift in this context as “anything, whether digital or physical, that you send the prospect’s way that’s personalized to them. If it highlights a connection between the two of you, even better.” For more on that, here’s a blog you can check out.
“So,” said Danny, “I’ve created a GPT where you can just upload a blog resource or a link, and it will spit out a gifting, natural-sounding, organic email that you can just go and use as a template for your teams.”
“We got served up with a 400-question RFP a week and a half ago,” said Matt, “with a June 20th due date.” There, too, he and his team used AI: “It didn’t answer a hundred percent but got through like 80% of the questions [leaving only mop-up work and proofing]…So far, it looks pretty good…”
Recently, Danny found himself preparing for a webinar he was delivering. He recorded himself doing it and then told Claude AI, “‘Look, just crush me on this.’ It gave me some good feedback.” He put the second draft of his presentation into GoogleNotebookLM, which created a podcast based on it. “When I was running, I would then play the podcast of my webinar created to kind of learn in different ways and absorb the information in different ways.”
Toward the end of the conversation, Joshua evoked the Industrial Revolution: “prior to that, if you wanted to light your house, you killed the whale and took the fat and made oil out of it, and you know, if we kept doing that we would have decimated all the whales in the ocean. So, it’s a good thing that we made the transition to oil and gas and electricity…and everything’s always constantly in evolution.”
But Joshua doesn’t necessarily see this as a the more things change, the more they stay the same situation. “If you look at the timeline and the arc at which that happened, if you were in the whale hunting industry, you probably had like 50 years to get out of the whale-hunting industry. I think [widespread AI use] this is going to be violently sudden…” He pointed to the ebbing of entry-level positions that typically cater to the new-college graduate population. In general, he feels, “We do have time…but if you don’t use this time to like, build up your pace and cadence, and how you use it, you’re in trouble.”
“Like Josh,” said Matt, “I think I’m just as worried about the social consequences of that, and what that means when that change hits really really fast.”
At the close of the conversation, Will weighed in on where he sees some of the macro tea leaves blowing. There are “massive subsidies going into those companies, very similar to like how Uber and Lyft and Doordash, and all of those companies literally would charge 90% less than they are charging today, because they had massive war chests and were trying to buy market share. It’s very similar. There will be a bill that comes due at some point for AI, right? What that means is that it will likely replace the below-average performers; the average ones will still be employable, and the ones that excel and have learned to leverage AI correctly will be in high demand…” Will Fuentes is not one to mince words: “you’ve got to start adopting it.”
At the same time, many in the group admitted that it’s been a bit of a learning curve for them— as well as for AI, which depends on iterative use to improve (“the more I feed it the better it gets,” said Seth). Josh’s advice? Treat it like picking up—or re-picking up—running. “Start walking a mile, jog a little bit, do a little bit here and there, and within like a year you’ll be at a pretty good jog, and then, like two, three years, you’ll be competitively running…” Something tells me Joshua is built a little differently than I am, but his point is well taken: start small. Build up. Keep going.
And remember, AI might become a near-requirement in sales, but don’t ever, ever let anyone convince you that you have to take up running.
Is your pipeline problem too big for even AI to fix? That’s where we come in. You can reach us at mastery@maestrogroup.co.
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