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Inside the Mind of a Modern Sales Leader: AI, Forecasting, and Winning Deals - Scott Shillington - Advisor, Sales Excellence @ Pike Street Capital

Elite Selling Podcast · 2026-05-06 · 41 min

0:00--:--

Key moments - from our scoring

Substance score

50 / 100

Five dimensions, 20 points each

Insight Density10 / 20
Originality8 / 20
Guest Caliber13 / 20
Specificity & Evidence10 / 20
Conversational Craft9 / 20

Scott Shillington, advisor of sales excellence at Pike Street Capital and former head of worldwide commercial sales at AMD, walks through a framework for deploying AI in sales organizations that moves beyond hype to practical ROI. Rather than treating AI as an IT initiative, he positions it as a business transformation project focused on four measurable outcomes: 20-30% reduction in admin time per rep, 30% improvement in field completeness tied to stage exit criteria (especially MEDDIC documentation), 15% reduction in stage slippage, and 75% adoption within 60 days. The conversation emphasizes that AI should free managers from administrative work like forecast calling and deal summarization, enabling them to spend more time coaching reps on actual customer calls - where deals are truly won or lost. Shillington stresses that discovery is the critical stage and that reps often rush through it, leading to deals stalling with economic buyers who see no clear ROI or metrics. He also discusses whether AI might eliminate manager layers, concluding instead that AI should eliminate the administrative burden managers carry, allowing them to focus on field coaching. The episode covers practical workflows like using AI for account research, call summaries, MEDDIC gap detection, and risk flagging in forecasts.

Key takeaways

  • →Focus AI implementation on high-frequency seller workflows (research, call summaries, MEDDIC documentation) rather than top-down mandates to gain rapid adoption and measurable productivity gains.
  • →Discovery is where deals are won or lost - rushing through discovery to move deals through the pipeline creates stage slippage and lower close rates, so AI should free up rep time to conduct thorough discovery conversations.
  • →AI should eliminate manager administrative work (forecast calls, manual deal summarization) rather than eliminate managers, enabling them to spend more time coaching reps on customer calls with better data.
  • →Implement AI as a business project focused on four key outcomes: 20-30% reduction in admin time, 30% improvement in field completeness, 15% reduction in stage slippage, and 75% adoption within 60 days.
  • →Optimize the AI capabilities already in your existing tool stack (Salesforce, call recording platforms, CRM systems) before buying new point solutions to maximize ROI on current investments.

Guests

Scott Shillington

Topics in this episode

Discovery processSales enablementAI in salesMEDDIC frameworkSales velocity and forecast accuracySeller admin time reductionPipeline qualityStage slippageCall recording and summarizationPike Street Capital

Questions this episode answers

How should companies implement AI in sales organizations without top-down resistance from executives?

Focus on bottom-up implementation by targeting high-frequency seller workflows like account research, call summaries, MEDDIC documentation, and risk detection that deliver clear ROI within 60-90 days. Position AI as a business transformation project that frees up both rep time (20-30% admin reduction) and manager time for coaching, rather than an IT initiative.

What is the most critical stage in the sales process where deals are won or lost?

Discovery is where deals are won or lost. Reps often rush through discovery to move deals forward, but deals that lack clearly identified customer outcomes with metrics have a 5% win rate versus 75% for deals with verbalized outcomes and metrics. Taking time in discovery saves time downstream.

Will AI eventually eliminate frontline and second-line sales managers?

No - AI should eliminate the administrative burden managers carry (forecast calls, manual summarization), not the managers themselves. This frees them to spend more time coaching reps on actual customer calls in the field, where deals are truly shaped.

What are the four key outcomes companies should target with AI implementation?

Increased sales velocity and forecast accuracy, reduced seller admin time (20-30% per rep), standardized processes across the business, and a portfolio playbook for AI-enabled go-to-market with metrics like 15% reduction in stage slippage and 30% improvement in MEDDIC field completeness.

Should companies build custom AI tools or optimize existing tool stack capabilities?

Most mid-market companies should first optimize the AI capabilities within their existing tool stack (Salesforce, call recording platforms, CRM) before buying new point solutions like People AI or third-party vendors, as many organizations underutilize the AI already in their platforms.

What our scoring noted

Our reviewer’s read on each dimension, with quotes from the episode.

Insight Density

10 / 20

The episode delivers a handful of concrete frameworks - a four-area commercial AI model, specific KPI targets, and a discovery win-rate contrast - but large stretches are filled with generic platitudes ('be a voracious learner,' 'be an athlete') and circular conversation that dilutes the overall density.

we have a win rate of like 5%. But uh, we have a win rate of like 75% if we've got coming out of discovery, you know, a, uh, clear outcome that's prioritized with metrics
30% improvement in required field completeness tied to stage exit criteria

Originality

8 / 20

The central ideas - AI reducing admin burden, discovery as the deal-making moment, MEDDIC qualification, mutual action plans - are well-established in sales circles and receive no genuinely contrarian treatment. The critique of Salesforce as a management tool rather than a seller tool and the PTC anecdote are the closest the episode comes to a fresh angle, but neither is developed.

at PTC in the 90s, storytelling just was not allowed. It was a very data driven company. You had the evidence.
Salesforce wasn't enabling the salesperson... it was like seen as this heavy management tool

Guest Caliber

13 / 20

Scott's seven years running worldwide commercial sales at AMD and current work advising 10-12 PE-backed portfolio companies on go-to-market give him genuine practitioner credibility. His advisory/consulting position rather than active operator role, and the lack of named company outcomes in the conversation, keep the score from climbing higher.

Previously he was a seven year veteran at AMD where he ran worldwide commercial sales
I get to work with the entire portfolio of our companies. There's about 10 to 12 of them right now. And really working with the CEOs and their heads of sales or revenue to help them optimize and accelerate growth.

Specificity & Evidence

10 / 20

The episode does surface specific metrics (5% vs. 75% win rates by discovery quality, 30% admin reduction, 90% activity capture, 15% stage-slippage reduction, 75% rep adoption in 60 days), but these feel illustrative and aspirational rather than verified outcomes from named clients. Company references stay deliberately vague throughout.

we have a win rate of like 5%. But uh, we have a win rate of like 75% if we've got coming out of discovery, you know, a, uh, clear outcome that's prioritized with metrics
75% of your reps using AI workflows within 60 days

Conversational Craft

9 / 20

The hosts land one genuinely sharp question - whether AI-driven forecasting could render frontline managers obsolete - and usefully prompt Scott to define mutual action plans for the audience. However, the established mentor-mentee friendship prevents any real pushback, claims go unchallenged throughout, and the hosts frequently redirect conversation to their own experiences rather than pressing for deeper evidence.

Do you think we'll ever get to a place with the AI rolling out? Like, I'm thinking about forecasting, risk management, medpic. Do you ever feel like we're heading towards a place where the need for a frontline manager or even a second line manager goes away?
a mutual action plan for those listening, can you explain what that is just real quickly?

Conversation analysis

Computed from the transcript - who did the talking, and the words that came up most.

Share of words spoken

  • Speaker A71%
  • Speaker C18%
  • Speaker B11%

Most-used words

sales44back23trying21data20customer19call18level17forecast17first15discovery15meeting15scott14tools14agents13help12deal11

Episode notes

Episode Summary In this episode of the Elite Selling Podcast, Frankie and Griff sit down with sales leader and mentor Scott Shillington to break down how AI is fundamentally reshaping the sales profession. This isn’t surface-level AI talk. Scott shares how top CEOs are thinking about AI, what’s actually driving revenue (vs. hype), and how elite sellers are using AI to gain a massive competitive edge. From forecasting accuracy to pipeline quality to eliminating admin work, this episode is a blueprint for how to sell at a higher level in today’s market. If you’re still using AI like Google… you’re already behind. What You’ll Learn Why discovery - not closing - is where deals are won or lost The 4 AI priorities every CEO actually cares about How AI is eliminating forecast guesswork and emotional selling The real reason most pipelines are weak (and how to fix it) How to use AI to increase productivity by 20 - 30% immediately Why top sellers are building their own AI “agent teams” How AI is shifting the role of managers (not replacing them) The difference between average reps vs.

Full transcript

41 min

Transcribed and scored by The B2B Podcast Index.

Speaker A: Be a phenomenal networker, right? Making time in your calendar to connect with others inside, outside your industry. You've got, it's an amazing uh, career being in sales. The thing you take from it when you step away from sales is this career, this network you've built. And build the network at a deeper level than just transactional. You know, you're going to have a chance to make a network with people that have a meaningful impact on your life and so focus on that.

Speaker B: Welcome to another episode of the Elite Selling podcast. Your hosts, Frankie and Griffin. Today we have got one of our very first guests on the podcast, Mr. Scott Shillington, aka Shilly. Scott is currently an advisor of sales excellence at Pike Street Capital. Previously he was a seven year veteran at AMD where he ran worldwide commercial sales and is passionate about sales enablement and productivity. And today we're talking about AI, uh, how to use AI and deal strategy and everything in between. So our first ever repeat guest on the Elite Selling podcast here is Scott.

Speaker C: Scott, AKA Shilly. Welcome to the Elite Selling podcast. I think you were our first guest, so you are our very first guest guest and our first repeat guest. So welcome back.

Speaker A: Thank you so much. It's great to be back and it's great to see what you guys are doing, continuing to educate the field and up level, you know, our profession, uh, which is professional sales. So, you know, kudos to you guys for continuing to make the effort and, and doing it the right way. So thanks for having me today.

Speaker C: A hundred percent. Well, thanks for taking the time to invest in Griff and I. You've been a mentor of mine and a mentor of Griff and a friend of ours. So a lot has happened over the last three and a half years. Yeah, yeah. Since we first kicked off this episode. So you've had some good things, career changes, updates. So let's start with that. What are you up to since we talked last about three and a half years ago and then we'll get into the topic from there.

Speaker A: Yeah, no, I was fortunate enough to have a great run at uh, AMD and then get uh, to go step out and um, sort, you know, what I would say is I made a decision around time and space and I wanted to spend more time on the things that drove the most amount of enjoyment for me and that really led to the decision to, you know, hey, I'm at a place where I can kind of go make my own way. And so I founded my own business, REJ Sales Optimization. Um, and uh, so, but really what that Means is I'm spending a lot of time with Pike Street Capital, a private equity firm based out of Seattle, as their sales excellence and go to market person. And so I get to work with the entire portfolio of our companies. There's about 10 to 12 of them right now. And really working with the CEOs and their heads of sales or revenue to help them optimize and accelerate growth.

Speaker C: So you could, after you quote unquote, retired from amd, you could do anything. You could have gone golfing, boating, just working out, doing what you do. But you're still here talking about sales. So it's in the blood.

Speaker A: It is. It's so much fun and uh, you know, it's changed so much. So I think if it stayed stagnant and there wasn't anything new happening, it probably wouldn't be a lot of it wouldn't be an interest to keep pushing forward. But I still find myself signing up for sales training courses, staying on what's the, you know, most impactful developments in our space right now and how to translate that into the language of the different, uh, portfolio companies. And I also am staying busy. You know, I've got a number of nonprofits I'm working with and um, sitting on some boards. And it's really interesting how we take the application of what's happening in today's marketplace into those areas as well. So I think it's the most, as I say to so many CEOs and heads of sales, today feels like the most exciting time to be in sales. Just given what the developments with AI and the level of professionalism you could bring to this space.

Speaker B: Absolutely. So let's talk about it. I mean you mentioned you're talking to CEOs around what's going on in the marketplace today. Obviously AI is the number one subject. Any discovery recall I go into, I'm sure Frankie as well, nbm, um, it's all around how are you going to help our AI strategy? What's your AI model, all this stuff. So would love your perspective on some consistent themes. You're hearing from kind of the upper echelon CEO level at some of your portfolio companies and what's moving the needle the most. But would love your take.

Speaker A: Yeah. Different than using it as a research, which is super critical. Right. In getting ready for discovery meetings. When we're sitting with CEOs, we're trying to think through what would be the most effective way to implement AI because uh, from a top down standpoint, that that can be very hard. Right. And you have to think of like the readiness around your data sets and you know, do you have clean data? Do you have, can you connect your different data models and then what outcomes do you want to get? What I've been Talking to the CEOs about IS readiness, right? So what would be the outcomes they'd want? And we think about, uh, this repeatable commercial AI model. I think of four big areas, right? Increased sales velocity and forecast accuracy at a CEO level, that's super important to them. Reduced seller admin time. If you think about one of the big cost drivers on your OPEX line, it's seller cost, right? So adding new salespeople is expensive. So if you can reduce the amount of admin time, that means they get more selling time. That should translate into increased revenue. We can just get people selling more. We get more scale out of the staff. We have standardizing processes across the current business. And when we think about acquiring a company, how fast can we integrate them? So using AI tools to do that, it's a huge benefit. And then establishing a portfolio playbook for AI enabled go to market. And there's so much m, so many areas. So it's word salad. If you think of running sales plays, how could you start to utilize AI to help you create sales plays and so you can get your salespeople down the field farther? How could you help your salespeople find higher fidelity target customers? So in those four big areas is what we're trying to think about at an executive level for this commercial AI operating model.

Speaker C: Okay, what's been like the biggest, I guess, challenge. Let's start with that, that you're running into. If you're rolling this out and saying, hey, this is the new way, and what's the most resistance you're getting from CEOs, CROs, executives, if anything comes to mind?

Speaker A: A lot of the challenge, um, for the CEO is how much time and space they can devote to this part of the business, right? If you think a CEO, it's just a high demanding job because they have responsibility for, you know, overseeing the entire company, whether it's operations, finance, and what's really hitting kind of their agenda that month, that week, that day. And so the big challenge for us is making sure that we're laying out this potential utilization of AI in such a way that it hits kind of top three or four payback opportunities. They invest dollars, are they going to get a return? And so speaking to them in such a way that as you should, on any large deal that you're trying to sell, you're trying to what's the outcome we're working to deliver and then if that outcome makes sense, how would they prioritize that outcome against the other projects that they're trying to get delivered that year? And AI should be able to give us like a high return outcome. And if we're doing it properly, it should get prioritized. And so for us, you know, it's making sure we're speaking the CEO language and not trying to confuse or like here we are rocking up with yet another consulting firm that's going to take a ton of drag on the company and no one's going to be able to see the outcomes. And this is why I believe it's best explained against those four initiatives I was talking about and driving it from the bottom up. Because if you could, if you, if you focus on like high frequency seller workflows, so you guys are sellers. If we focus on the things that you're touching a lot, right where it's like account stakeholder research briefs before meetings, can we make that super effective? Could we train the team on how to use AI? So now you're rocking into a meeting and you've got a much higher level of like research done, but you know the types of questions to ask and you know how to work through that dialogue on discovery, whether it's an executive or a manager, et cetera. Right. Call meeting summaries One of the big challenges is we think of the velocity with which you all are selling at these days is the managers are being pushed to do so many other item actions and they're not as close to you as you'd probably like. So how can we then leverage AI to get a better summary of the work you've been doing condensed so they can coach more effectively across the limited time they have? Medic gap detection, mutual action plan quality, you know, are we driving insights into that pipeline? Risk flags A big thing that CEOs care about is an accurate and timely forecast. Is the sales leader making an accurate forecast for the current quarter, for the current month. So how can we leverage AI to help us understand where the risks are going to be in that forecast? Call and if I'm a CEO, I, I really care about understanding where the risks are so we can engage earlier and take actions versus coming to the end of the month and everyone throwing their hands up and saying we missed a number. I would much prefer to enable my CEOs to get a sense of when there's risk in the forecast and what actions they gotta take to support Sellers. And I'm sure as a seller, that's what I love too. It's like instead of like drilling on me and complaining, it's we're in action mode, not complain mode. Right. So that's important. And Scott, follow up in sequencing.

Speaker B: Can I ask you something really quick? Scott, let me ask you something. Can I ask you something?

Speaker A: Yeah.

Speaker B: Do you think we'll ever get to a place with the AI rolling out? Like, I'm thinking about forecasting, risk management, medpic. Do you ever feel like we're heading towards a place where the need for a frontline manager or even a second line manager goes away? If we can get to a place where a rep is running a deal and the forecast accuracy analysis is so tight that the forecast could just roll up straight from the rep to the CEO? Or the same thing with medpic analysis. Like the rep is filling out medpic and there's no need for a frontline, uh, manager to analyze or there's no need for a VP to this. I mean, this might be an unpopular take, but I'm wondering if, if you feel like we'll all get to a place where that whole process gets streamlined.

Speaker A: Good question. So my thinking that I've been doing around that maybe not the exact same question, but how the utilization of AI is going to allow us to be more effective in our jobs is I'm trying to get the manager out of the work that could be done more effectively with an AI tool. Like if we could infuse in all of the logic, right? And so we train the AI agent with the right logic on how to detect all these things. What we're then freeing up is the manager to actually go out in the field and spend more time with the rep on calls. And so then we're in front of the customer and we can actually put two people to work to help identify what are the outcomes the customer wants, get the customer to relate that back in their words and shorten the sales cycle for everybody if the customer has a true problem, it'd be much more effective if we could get that out of them and help them understand how they could create the business case and write the business case to get financial approval. Everything seems to get stuck in sales because we're doing a poor job on discovery. So if AI is going to free up leadership time and experience management time to support our reps in an environment where we don't train the way we used to, then I think, yes, I want to get there much faster because I don't. I Think that letting the tool figure out where the real risks are. There's no personal bias. There's no like, hey, it's my person, it's my gal, my guy. I got to make sure I cover for them. You remove all the bias, get to straight facts, and then you allow people to be people in front of customers. Customers again more of the time.

Speaker C: Yeah, that's what I was gonna say. Uh, uh, it's, it's data driven. It's not just emotional anymore like forecast used to be and still is, but trending away, such an emotional thing where it's like, you get in there and it shouldn't be, but it is emotional where you get in there and you're like explaining, hey, I got this deal, I got this deal. And, and you go back and forth. I mean it's, we're 10, 15 years away removed from that. But what you're saying is like, it's completely data driven at this point. It should be.

Speaker A: Yeah, it's, I think it's the culture that's created at the company where storytelling's allowed. Uh, you know, at PTC in the 90s, storytelling just was not allowed. It was a very data driven company. You had the evidence.

Speaker B: Yep.

Speaker A: And you had the live last meeting done or you didn't. There was no coming in and trying to talk your way through what wasn't there. And I, uh, AI inspection would allow us to just have the facts. And it, it's like you're trying to move this deal to scoping. Yet we know that our success rate of moving to scoping without having a clearly identified customer verbalized outcome with metrics tied to it is like, we have a win rate of like 5%. But uh, we have a win rate of like 75% if we've got coming out of discovery, you know, a, uh, clear outcome that's prioritized with metrics. Now you get to the scoping meeting where you're validating all of that, you're going to drive home closure at a much higher level. But so many salespeople just want to move the stuff through the process because they got to get out of the forecast call the most uncomfortable call of the week. And so they're trying to storytell their way through it. And then by the time the rep, the manager has such an inefficient process, most of the time they're exhausted by, they get to the fifth rep, they just like just doing math in their head. How much am I discounting all of this person's forecast? So I know what the roll up I'm going to make.

Speaker C: Yeah.

Speaker A: All that stuff is better done with AI.

Speaker C: They have enough for you.

Speaker B: It's like I wonder if there's ever

Speaker A: a place I'm a hundred percent with you, Griff. I'm just saying the outcome for me is then I'd get more manager time in a higher quality environment because they're not going to be spending their time doing that stuff and they could do their homework more effectively.

Speaker C: Well, and on the prep, I uh, think it was on the prep, I don't think we were live yet. But you were talking about the ratio of how many reps do you need versus what's the traditional ratio versus how many reps per team. And I think what this AI and forecasting and all the tools that take off the administrative burden do is allow you to have a smaller pool of reps, cover more ground, but cover it more effectively and just pump all those resources around your best people. So like you create a superstar team, so to speak.

Speaker A: Yeah. That focused on the highest fidelity customers. The ones that.

Speaker C: Exactly.

Speaker A: Uh, right now unfortunately a lot of reps are spending a lot of time with people that are never going to buy and so making sure we're spending our time with the customers that are going to buy and that's where agents are going to allow us to dig deeper into the data. So, you know, I see those ones as a great question, Griff. I think we all aligned around a common answer. You know, that it's a much better way to go and it'll be a much cleaner environment. So the other area that we talk to that I'm talking to the CEOs about are uh, the key KPIs, right. What are these measurements that we should be looking at every week? Right. And if we could, from a seller productivity standpoint, if you could pull 20 to 30% reduction in admin time per rep, that's like, you know, 90% activity capture without manual entry. I mean, so you get a bump on each player by 30% and you get accuracy of all of the activity they do like 90% level of accuracy.

Speaker B: Yeah.

Speaker A: I mean that's if I told both of you. Oh, by the way, starting tomorrow you're going to get an immediate 30% productivity bump.

Speaker C: All day.

Speaker A: All day, Right?

Speaker C: Yeah.

Speaker A: Because you're going to be. And then you could translate that into

Speaker B: be on the golf course, you know, letting an agent.

Speaker C: I'd be selling more.

Speaker A: Selling more because I got like the income. So if I could get to like 5x my quota, that'd be great. Right? I'd take that all day long.

Speaker B: But does that, I mean, I'm joking, but does that necessarily. Does the 30% administration bump automatically dramatically increase the revenue? Right. I guess that's kind of the thought process. But does that, does that, does that actually happen? Right. I'm trying to think of where I spend the most time as you know, doing administrative stuff. Frankie, where do you. Sending emails, scheduling meetings? Uh, you know, I think for big

Speaker C: deals, it's, it's coordinating resources internally and translating what you've heard. And I think what AI has done is it's taken the burden off of the rep to listen, pull out a notebook, take really good notes, pray that you didn't miss anything, come back, write it up in an email, all the things that go into it. Now, every single call should have some type of meeting note taker that automatically goes back to the system of record. That to your point, Scott, I'd love to get into this later or now, but agents can go and orchestrate where the data goes to the right people. And now you're not having to play telephone across multiple people. If you already go focus on these

Speaker A: big deals and you're going to be so much more focused on the customer coming in to the meeting where so many people are distracted rolling into the meeting because they're just moving from activity to activity. They're not doing justice to the discovery call. And so there. And the discovery call largely where we set the deal up for win or lose. Because you should.

Speaker C: Stole that advice from you. I've been running with that. Uh, I love that. Say it again. Discovery is where you win or lose.

Speaker A: Yeah, Discovery is where we're winning or losing the deal. Because it's like, it's that moment where you're identifying, do you have a real outcome? Have you figured out the customer's outcome? Do they have some truly true problem they're trying to fix that you could align with that. You've got clear, demonstrable metrics you've done before that would deliver an ROI that they can go and take and sell. Like, it all happens in discovery. And what happens is everyone tries to move through discovery too fast. They want to get to some lightweight validation. And then their struggle with delay or no interest or no close because it can't get prioritized. The CEO or the economic buyer is like, it's nothing here. I got other problems.

Speaker C: Yeah, and moving stuff off of your plate. Like, think of the days of, okay, I'm on a call, have to take the notes have to do this and then I don't have enough time to do it. So then you're half prepared for the next meeting. Now you can have all of your, your notes, you know, they're recorded so you could spend five minutes at the end of the day pushing them to where they need to go so that you can be totally present on that discovery call and prepared with like the best information because of AI. So that you can sit with that.

Speaker A: Uh, yeah. So think of like five big buckets, right. One on seller productivity. So like this 20 to 30% bump, right. Pipeline quality, a 30% improvement in required field completeness tied to stage exit criteria. Like this one is super important. Right. Medic fields populated greater than 80% of the qualified deals. So you've got the evidence. What are the whatever qualification language you want to use. I like medic. I equate it back to getting the evidence that the customer would speak the words that we are documenting. And then sales velocity. So you'd have a 15% reduction in stage slippage. So that's faster time from first meeting to next committed stage to all this stuff just. And from a customer standpoint, if they're in, they're happy because you're moving quickly to get to the, if there's a real outcome that they need and you can deliver it, you're moving more, you're, you're taking less time and so they're happy. Right. And then forecast accuracy reduction in late stage deal movement. Number one burner for so many sales leaders is all this late stage slippage movement. By the way, I'm just calling the person, I'm checking in all the bad things. Right. You get rid of all that late stage craziness so you improve your commit accuracy versus prior quarter pipeline base. Right. Versus prior quarter baseline. So you're also then from a leadership standpoint, you're lifting up your quality and then you're driving more confidence back into yourself from your leadership team. So what the CEO wants is confidence that the sales leader is making an accurate forecast. Because the CEO at all these PE backed firms, they got to get on the phone with the board and the PE firm every week.

Speaker B: Yeah.

Speaker A: And that's just. You think your pipeline inspection is uncomfortable. Guys, that's an, that's an uncomfortable meeting. So how do you. They need to get the confidence so I can really drive this. And then adoption like you get 75% of your reps using AI workflows within 60 days mean.

Speaker C: Yeah, it's a game changer.

Speaker A: Right. So to Me, I think it's not, it shouldn't be penned as an IT project. Right. It's a business project and it's a super critical one. Right. So there's going to be lots of different owners in it, but that's the way we're thinking about it at the CEO level.

Speaker B: Curious if at the CEO level there is a consistent theme around, you know, leveraging more AI from third party SaaS applications like Salesforce and Gong and Clary or people AI shout out or if it's more focus on you know, first party AI, you know, developing your own kind of homegrown AI or, or just hey Griffin and Frankie, use Claude or ChatGPT to do your own work. Like uh, help, you know, use ChatGPT to do some of your administrative work. We want more of that, like use that as more of a bot or an agent.

Speaker A: My experience would say that Most of the CEOs don't have that type of fluency around. Yeah, what's like zoom info and all these other tools. Right. And I know one of Frankie's former clients that's using people AI. I think they're making some big strides with it. So you know, great to see that. However, at this mid level company size it's important that they get there. And where we try to think about is the tool stack. Have you optimized the use of the AI capabilities inside the tool stack? So if you have like a uh, call recording technology, are you utilizing the, the tool that they have the AI capabilities inside there? That's I think that's a tool level discussion. And why buy the tool if you don't optimize it? So it's optimizing the stack you have is one the more effective way I, I think are these agentic AI tools or the Claude claw where you're going in and you're actually building agents and teaching your team how to build the agents so they can get to the data that they want to summarize, like the dashboards. Everyone was all big on these standardized dashboards but everybody's different on what they need. If we had AI agents, I get to build the dashboard that's most effective for me.

Speaker C: Are you seeing people adopt these AI agents even at uh, like the mid market SMB or is it more enterprise from what you're seeing?

Speaker A: So I, it's uh, interesting one startup, it's a buddy of mine's company so we spent a lot of time together seeing that ramp and it's had a phenomenal ramp. The AI implementation there is from the grounds up. So it is using agents that they're programming on their own, not buying heavy tools. And uh, it's interesting because the immediate applications that they're going after we're you know, discussing, but I know they're going after is deal inspection and forecast integrity right there. Right. So AI pre scoring, medic gaps, EB access like mutual action plan ownership and risk flags before managers enter a review. So it's like uh, that's key.

Speaker C: Right.

Speaker A: And uh, and so they allows the managers to inspect evidence, not sifting through notes. And really to be effective managers, that's where you want coaching as a salesperson. And if I ask the two of you guys right now, how much coaching do you get on a weekly basis around evidence, not in your pipeline versus just asking you to do some like check the box stuff.

Speaker C: I feel like I get coaching because I'm, I'm doing all the things you're talking about. I'm not. My company is. I'm fortunate you're doing it yourself. Well, I'm doing it myself but also like I have tools like my company's is doing what you're talking about where you're uh, building and agents on your own and all sorts of stuff.

Speaker B: I would, I'm kind of on the opposite spectrum. Whereas I'm in a startup so we don't have a ton of sales enablement resources. Our leadership is spread pretty thin. So I'm actually huge on AI self enablement. Like you know, you kind of have to own it yourself, your own enablement and it could be around product, it could be around your customer, it could be around discovery, it could be around you know, NK analysis. Right. I mean I think there's, there's plenty of different ways if you're curious enough to. It's all about asking the right prompts and just being, being curious enough to mess with.

Speaker A: Uh, and to me it comes back to a couple of pieces and I'll keep going through some of these notes. What I always try to encourage the sales leadership is to recognize that each person needs admin time every day. If they're productive, get all their prospecting ready, et cetera. But there should be self development scheduled into your calendar every week. If you've got an hour or two hours, I mean that's plenty of time for you to do the research on this and then start applying it. Right. So. But I think in the big areas where you've got like some of the startups you guys may be selling to or working with, there's the deal Inspection forecast, uh, integrity, commercial assessments, assessments, analyzing CRM exports, call transcripts, pipeline metrics, draft through the first 80% of like CEO ready diagnostics. So getting the CEO ready with that type of information, Win plan and mutual um, action plans, which I think are really critical in today's selling and strategic deals. Right. If you don't have a mutual action plan with the customer, what they're owning and what they're going to get and you're not inspecting it,

Speaker C: a mutual action plan for those listening, can you explain what that is just real quickly?

Speaker A: Yeah. So when you're sitting there, you've gone through the discovery call, you're now let's say in scoping where you're trying to collect information back and forth with the customer, you create some like shared Google shared document and you assign by the way Frankie, you're responsible for getting this data from your company internally. And then what I'll do is I'll ingest that information and turn back and prepare a demonstration of our product with your data. Right. And but we need to get that by the 10th so we can do the demo on the 12th because we need two days to prepare. Make sense? It's like, or I need to get a meeting set with your lawyers as we're working through the paper process so we can hammer out details that might be sticky on both sides. So let's get that meeting scheduled and assigning that. Right. And having the evidence that you've actually taken the step to get the next business meeting locked.

Speaker C: Mm mhm. Yeah. And ideally it's, it's you know also I've heard it called mutual close, uh, plan where ideally it's towards a, an event that the customer has, not necessarily something that sales has created. Because it's my end of month or I need to hit my quota, it's more, hey, I've got a rollout that I need to do or I've got this big project or whatever the case is for the customer and then you're reverse engineering from there so it's outcomes

Speaker A: you've found in discovery. The customer's like hey, we need to make these improvements. When do you want to make those improvements by Great. So um, we should land work backwards if that's the case. What are the dates we're going to do it on? So great close plan closer to the close process, mutual action plan during the process. But commonalities prospecting intelligence. To me there's nothing right now that's baseline. Every salesperson on planet earth should have prompts. They should Be going and getting best available prompts to and then they should be simulating big meetings before they're doing it, walking through using uh, chat, you know, AI tools to get them there. But all of your pre meeting work, it's like having the best assistant in the world. Yeah, I mean it's unbelievable. Right.

Speaker C: So yeah, let's, let's talk about just uh, we've touched on it a little bit but just to really clearly state it out and get your guys opinion on this. But like the evolution of, of AI specifically within sales. We talked about this on the phone one, one day and we're like we need to do a podcast on this. So we were talking first of all, you know your large language model, whether it's ChatGPT, Gemini Claude Copilot.

Speaker A: Right.

Speaker C: Everybody's familiar with that. It's like Google on steroids and most sellers are using that today. That's phase one in my opinion. Phase two is what you've mentioned a few times Scott is this agentic workflow where it's using natural language and pulling things and pushing them to you automatically so that, okay, you can pull my calendar up. Uh, I've got a meeting with XYZ company with this title. I'm going to pull the data you need without me as a rep having to do anything. Um, and then follow up with notes, send them to the right people, bring in your se, bring in your leadership team, whatever you need to do. And then that's more like you could today use natural language with agents to go and build what, what we call at my company super agents to go do that for you. And then the last piece is, is what, at least what I've heard it's called certified agents where it's like a standardized workflow for maybe something beyond like a seller's day, but maybe like a sales ops or a rev ops day. And now you're manipulating all of this data on the back end that's standardized and not being touched by. And so you talked about bringing in these virtual assistants or agents to help you where you as a seller is going to have this virtual team. Like can you tell us a little bit about what you're seeing in some of those points?

Speaker A: So it's interesting you laid out the roadmap very well. I would say it's early adoption and what we're trying to drive at the level, um, you know the size and space of the companies we're dealing with is getting the sales level data built in and some of our more advanced companies sales, uh, Ops, um, leadership teams are way down the path utilizing and building tool sets that are driving, you know, the, the analysis that is needed to inform whether you're a CRO or CEO about the business and tying together the information. The earlier use cases, it was interesting on um, like going through all their data sets to get their data clean. And so that's a big area of also readiness. Right. So if you back up earlier, it's like your data has to be in a decent place for you to realize good outcomes. But the rev ops and sales ops teams, to me standardizing a lot of their workflow processes, utilizing this then lets them think about higher order problems versus trying to just turn through all the data every week. So I don't know if I'm answering your question, Frank.

Speaker C: You are. Yeah.

Speaker A: But to me where I'm seeing a shift in workflow is now that if you've got like the AI operating system at the sales rep level. Right. So it's like account research agent, medic inspection agent, pipeline risk scanner, Objection, Rehearsal simulator, org, Chart builder, weekly self coach. I think those are the big topics you, you covered. Right? Those are the ones that I'm a salesperson, I want to drive. Then we talked earlier about the CEO is trying to get much better fidelity around the, the forecast call. They've got to have a tight forecast call. So do they know, do they get early warnings? Are they understanding from AI tools that they get a better insight into where the company's gonna be at on the forecast, so the types of reporting there. Then there's all the people that run the world of sales, right? Sales ops, rev ops, customer service. And so um, leveraging AI tools to bring that data together. And so we get a better holistic insight. Right. Like here's what we need. The company didn't do enough calls last week. So we can, we can already predict we're going to have less meetings and we're going to have a degradation in our pipeline in four weeks. So now we can take a quick, we can run a sales play, ramp our calls back up and over index this week so we can rebuild the velocity we need. Like think of how much more powerful that is. Like now your sales ops person is like going, hey guys, prediction model says that we're, our pipeline's gonna get damaged because we had two weeks where we had like low call volume. So we need to take this high impact sales play and have everyone stop what they're doing and run this to ramp back up to a 200% of what our normal volume is to get our pipeline back to where it will need to be. I just think that's where the AI tools are going to go or that's where they should go because then we're going to be on top of all the processes that lead to the revenue outcomes.

Speaker C: Now you don't have people in RevOps digging through. You made too few calls. What do I need to do to go tell them it's just automatically bubbling it up for you?

Speaker A: Yeah. And then the RevOps person can go work with marketing and go, okay, we got a gen app like a high impact sales play and we need to go and P4 verticals were in our ICP that we haven't touched in a while. And then train all the reps so they can get all the training material built, pull all the reps into a training call, get them all to practice real time, giving them the AI prompts. So then they pull all their prompt information, build a bunch of sequences and just go mhm. Think if somebody called you up on a Monday morning, Griff, and said hey, we looked over the last four weeks and your call velocity hasn't been down.

Speaker C: Uh uh.

Speaker A: I know we've been trying to tell you that. But here's what we're gonna do to rectify the problem. We're doing a training this afternoon on these high.

Speaker C: You're on A plays.

Speaker A: Pardon?

Speaker C: I said you're on a pip.

Speaker A: Yeah, you're on a pip. I mean I was trying to be kind of nice here. I get a. You get to get off the pip quick. So that is.

Speaker C: Sorry you're saying.

Speaker B: Yeah, no, re.

Speaker C: Keep going with the training analogy. I was just trying to make a bad joke.

Speaker A: Yeah. Uh, no, but the world we're moving into, this is where I come back to what we started with. It is the most exciting time to be in sales because the empowerment of the salesperson is starting to become the best it's ever been. I think the salesperson was left in the dark for lots of years and it was like Salesforce wasn't enabling the salesperson. I don't. Sorry, Mr. Benioff, but I think it was like seen as this heavy management tool. But the reality is the CRM was always meant to empower the salesperson to give them the insights. But because the data explosion happened, you're just overwhelmed in what do I what it's like you couldn't tell the signal to the noise and to me the AI agents are going to tell us exactly what the signal is and where to focus at an Individual.

Speaker C: Mhm.

Speaker B: So let me ask you this Scott. If you were jumping back into the seat, if you were starting your career in sales, what would you do differently? Like how would you approach, how would you approach, you know, picking a company that you think is going to win? And then how would you implement AI in your day to day? Like if you had to summarize, as we kind of head towards the summary,

Speaker A: the chat first, I definitely would go back to the default of best company available, best, uh, product wins. So I would always look for whatever market I was going to go into. I don't want to be in the market leader. I loved that. I would go back to what I was just reviewing if, because I would take the coaching I give young salespeople that I mentor. Right. I would get myself ramped up so much on making sure I'm fluent in all the AI tools available and then I wouldn't make excuses about what the company doesn't have. I would go out and create what I need from the resources that are available. I've never worked in the perfect company with the perfect set of tools, with the perfect product at the perfect time. It's never happened in my career. Do more of now as you can get yourself into an advantaged position where you've got the best research available for you, you've got the best tool to understand, where you've got gaps in your sil, in your qualification process, you've got the best tools possible to do rehearsal, simulation. I mean I don't have to wait for a manager. I can just run role play. It's phenomenal. I can get three or four people looped in or like finding information about companies like building or charts power bases where I've got to sell and then weekly self coaching. And I would build also mentor groups that uh, the other biggest thing that I benefited from in my career is mentorship groups. Uh, there's nothing more powerful than getting with your peers on a weekly basis and working through like, here's what I learned about the AI toolset, here's where I'm implementing it. Show me exactly how you're implementing it. Uh, and I wouldn't do it all in the same industry. I would pick people in different industries. Yeah. As a salesperson I would take the medicine I'm trying to coach people on. Lastly, one thing that I continue to see that's needed is it's a hard job and I don't care how many AI tools you've got, you've got to be uber disciplined around your time Management and do the hard work. Prospecting, prospecting, prospecting. And even I'm, um, picking up 30% back in my day, then I should be applying that to the highest impact items and so I can get to the over plan as fast as possible.

Speaker C: So one thing that is a common theme even three and a half years later, since we had John the first time, is, is just always be learning and treat your job, AKA being an account executive, account manager, sales rep, as a profession. You know, and the analogy you made was professional sports, professional musicians, whatever your profession is, they treat it like a profession. They train, they drill, they get coaching, they have groups they talk to for mentorship. And that's just, uh, a key theme that you keep bringing up. And I think it's really easy, even, especially with AI, not to counteract what we're talking about, to kind of get in your own world and just use AI as your coach. But, like, it still is so important to, you know, rehearse and develop and do those things. So I love that you're still talking about that today.

Speaker A: Yeah, no, and I think you guys are great examples. This is why it's so pleasure, uh, such a pleasure to get to spend time with you guys on this pod, but off making, you know, having calls, is you have this, like, thirst for learning. And Frankie, that's really, to me, I was so fired up that day after you were talking about how you were doing the implementation, then I went off and I was like, okay, like, how can I learn more about this? And then how can I talk to other people about it? And the more you're asking questions and trying to seek to learn, then it's like you get to ramp into the world yourself. And to me, just AI is this part of this daily. It's like open full time on my desktop. And it's the way I've learned to be so much more productive than I ever was before. So I get to learn more, which is great.

Speaker B: Yeah, there you go. You get to learn more. Yeah, I love it. Um, it's open on my desktop right now, actually. Yeah. Prepping for this. What should I ask Scott? You know, give me some questions? No. So, Scott, this is great. I know we're, we're wrapping here, so we'll wrap on this one. And this is, this is gonna be the first time we've ever asked this question to the same person twice. We get to, we get to compare your answer now versus three and a, you know, two and a half years ago, whenever it was when we first met, you or when we first recorded. So give us your definition of an elite seller.

Speaker A: So fundamentals one. I'll, uh, go back to what we just saw. You have to be educating yourself all the time. There's just the market moves so fast, not only in the world of sales, but educating yourself about the market you're in. So when you're moving from, you know, different vertical to vertical or what have you, you have to just have a real hunger to understand the customer's business. The better you understand the customer's business, the better you're able to help them out and achieve the outcomes they want. That's what we're here for, is we're here to help the customer achieve their outcome. So just have a deep desire to know your industry that you're in, um, and just be like, um, a leader in that and take the time to ramp yourself up so you speak with knowledge and proficiency about the world you're in. So educating both your skillset and educating about the world you're living in. I don't know if I said it before, but you gotta be an athlete to be in sales. I'll, uh, come back to it. Whatever the version of the athlete you want to be, it's a very hard job. It's very demanding. It physically takes a toll on you. So you have to do the training to stay in the game. In my opinion, you have to be whatever version of athlete you want to be, be an athlete. It'll help, uh, you have practices that ensure that you've got good mental health. It's a very, it's a hard space. And so you've got to be figuring out how do you keep your mental health and how do you stay in a very positive environment because people want to spend time with positive people and super important and be a phenomenal networker.

Speaker C: Right?

Speaker A: Making time in your calendar to connect with others inside, outside your industry. You've got, it's an amazing, uh, career being in sales. The thing you take from it when you step away from sales is this career, this network you've built, and build the network at a deeper level than just transactional. You know, you're going to have a chance to make a network with people that have a meaningful impact on your life and so focus on that. So I'd say four things. Continue to be a voracious learner, both inside your career set and both the industries you're in. Make sure that you're spending time physically training yourself and being ready for the demands of the job. Uh, it's very hard. Be this great networker and take, uh, care of your mental health.

Speaker C: Love it. Scott, thank you for jumping on. We appreciate you. We'll have to do it again soon. Hopefully we'll see it see in Nashville sooner than later.

Speaker B: Absolutely.

Speaker A: Good luck to you guys. Continue to crush it and, uh, um, deliver top results for your companies. I know they appreciate you.

Speaker B: Thanks, Scott.

Speaker C: Thanks, Scott.

Speaker A: Yeah.

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