Sales POP! Podcasts · 2026-06-24 · 23 min
Key moments - from our scoring
Substance score
43 / 100
Five dimensions, 20 points each
Glenn Fleischman, Chief Revenue Officer at AYTM, an AI-powered consumer insights platform, discusses how sales leaders and teams should navigate rapid AI adoption by trading low-value work for high-value work. Fleischman draws from two decades leading revenue teams across SaaS, MarTech, and enterprise technology, arguing that the salespeople who will excel are those with strong discovery frameworks (SPIN, MEDDIC), empathy, and relationship-building skills - precisely the capabilities that AI automation will free them to focus on. Rather than replacing enterprise sales reps, AI handles the grinding tasks: data cleaning, outbound messaging, prospecting, and pricing. However, Fleischman cautions that organizations must first validate their sales motions with humans before scaling with AI, and must ensure clean, comprehensive data capture across all communication channels (phone, Zoom, LinkedIn, text) or risk giving AI an incomplete picture. He describes building "sales caddies" - AI companions that provide just-in-time enablement and context during customer conversations - as the lowest-hanging fruit for immediate impact. For job seekers and existing sales professionals, the takeaway is clear: AI capability will become a mandatory prerequisite within two years, making prompt engineering and real-time research skills essential differentiators.
Salespeople who excel at discovery using frameworks like SPIN or MEDDIC, bring empathy to conversations, read the room well, handle objections effectively, and find additional stakeholders will thrive - none of these skills are being automated away in enterprise sales, and AI will free them to focus more on these higher-value activities.
They attempted to scale an underperforming outbound motion with AI before the human process was nailed down, resulting in scaled underperformance; they learned that you must validate and optimize the sales motion with humans first before using AI to scale it.
They built "sales caddies" (AI companions called Skipper) that provide just-in-time, contextual guidance on what to say, how to sell, and what features do for different personas, eliminating the need to search through training materials and making enablement available in stride during customer conversations.
Text communications between reps and prospects weren't being captured in their CRM or call recording tool (Gong), so AI-powered forecasting and deal reviews had an incomplete picture; they're now working to include text communications in their data set while maintaining relationship-building conversations.
All job applicants must show a portfolio demonstrating AI capabilities and previous work using AI tools, and interviews now include live assessments of desk research and preparation skills using AI in real time.
Our reviewer’s read on each dimension, with quotes from the episode.
The episode surfaces a handful of genuinely useful practitioner observations - scaling bad outbound with AI amplifies failure, text comms missing from Gong creating blind spots, and 'sales caddies' as in-context enablement - but these are padded heavily with platitudes, filler affirmations, and generic AI-adoption pep talk that dilutes the overall density.
if the human process isn't right, if you haven't nailed the motion with humans, then AI, maybe AI can help you nail that and get that right. But until you get that right, don't try to scale with AI
those text communications were not making it into the deal flow. They weren't in our CRM, they weren't in our GONG review
The guest explicitly labels the central thesis a cliché ('it's become a cliche at this point'), and most takes - don't lose job to AI, lose it to someone who uses AI, eat the elephant bite by bite - are widely circulated; the 'sales caddy' framing and the live AI desk-research interview test are modestly fresh but not genuinely contrarian or first-principles.
it's highly unlikely in our world, enterprise sales, you're going to lose your job to an agent. M. You could lose your job to someone who's more effective at using AI than you
you'll be able to trade low value work for higher value work
Glenn Fleischman is a legitimate, currently-operating CRO at a real AI SaaS company with verifiable prior roles at Zappi, Invoca, and others, and he shares genuine internal mistakes rather than polished thought-leadership talking points; however, the conversation stays surface-level and he is not a scaled, well-known operator whose experience would attract a specialist B2B audience.
Our company is relatively new to outbound we were fortunate enough to get a lot of our demand through referrals and events and marketing content, organic, whatever. So we've only built an outbound motion in the last, uh, 12 months
we're building agents to be able to really take all the human out of that and to be able to effectively input into a screen a couple of data points and get back um, a really accurate price proposal, customer facing price proposal quickly
There are concrete anecdotes - 10 SDRs for the price of 2, Gong as the named forecasting tool, text messages as the specific missing data channel, 12-18 months of AI experimentation - but zero hard outcome metrics, no conversion rates, no revenue numbers, and no named customer examples to anchor the claims.
get 10 reps for the price of two. 10 SDRs for the price of two. What we found was our motion wasn't really nailed down
those text communications were not making it into the deal flow. They weren't in our CRM, they weren't in our GONG review
The host repeatedly validates every answer with 'that's a great question,' agrees rather than probes, and frequently summarises the guest's point back instead of pushing for specifics or challenging assumptions; there is no productive disagreement and no follow-up that unlocked materially deeper insight.
that's a great question
Yeah, and I think that's it. I think that's a great piece of advice is just start simple
Computed from the transcript - who did the talking, and the words that came up most.
Glenn Fleischman, Chief Revenue Officer at AYTM, explains how sales teams can adopt AI successfully by fixing their human processes first - then scaling with AI rather than multiplying a broken motion. He shares why enterprise sellers who master AI will out-earn those who resist it, and how AYTM builds research expertise directly into its platform. Learn more at
Transcribed and scored by The B2B Podcast Index.
John Golden: Foreign. Welcome to another Expert Insight interview. My name is John golden from Sales Pop Online Sales magazine and Coovera, formerly pipeliner CRM. Um, joining you as usual from a sunny San Diego and today I'm delighted to be joined from outside New York by Glenn Fleischman. How are you doing, Glenn? Hi John and Glenn. You're the Chief Revenue Officer at aytm, an AI powered consumer insights platform where you lead a revenue strategy and help organizations connect AI research and business outcomes. Over two decades of experience building and scaling sales and revenue teams across SaaS, Smartech and enterprise technology. You have been in senior leadership positions at Zappi, Invoca, Ninja Cat or Caden and uh, working across the us, UK and Asia. And you're a big advocate for people, uh, adopting technology rather than, you know, resisting it or embracing adopt technology rather than resisting it. Um, do you remember, I mean we've been through some significant technology changes over the years. Like maybe the Internet is the first, you know, was the, was the first really big one. Um, and, and your experience back then, how the, how has that shaped your experience today with, with technology adoption?
Glenn Fleischman: Yeah, that's a great experience. That's a great question. So, so sadly at my age, this is not my first rodeo. I've been through just about all the major technology shifts since I entered the workforce in 92. And uh, I had had a profound experience um, when I was a sales rep, a young sales rep, around uh, 95, 96, as the Internet was first coming into uh, and coming into sales. And um, we had customers who were starting to ask us for email addresses. They didn't want to mail us things anymore. So uh, you know, I go to my boss, hey, can I please get an email address, a company email address or at least, can I at least expense an AOL account or something? And in a scene straight out of the office, he uh, pulled us into the conference room, held up a computer monitor in one hand and a telephone in the other hand and said this, the computer monitor is a toy. This, the phone is a tool. If you're going to be a salesperson, use the tool. If you want to be a child, use the toy. So um, ever since that moment, obviously that comment did not age well. And ever since that moment, um, I've always had it really front and center of my mind to lean into every technology shift, whether that was, uh, the Internet, mobile, social media and now AI. Everything that's come along, you know, in this career I've had.
John Golden: And so what do you see like today? Because there's a lot of people very, very overwhelmed now because of AI and the pace of which it's come because m. As we said, the Internet wasn't overnight. Um, you know, even cloud computing took a while for people to move into the cloud. This is a breakneck speed and people are kind of, a lot of people are overwhelmed. What would be your advice to, to leaders and organizations or professions who are feeling overwhelmed?
Glenn Fleischman: Yeah, well, they say the way to eat an elephant is bite by bite.
John Golden: Right.
Glenn Fleischman: And I would say the way to take on AI is the same exact way. It's, it is overwhelming by the way. It's overwhelming for me. Um, it's overwhelming for everybody. So, um, I don't think you need to feel like you're ready to run OpenAI tomorrow. But everybody can start with the smallest little things. Um, for example, I used my Claude, uh, account to train for this podcast. I consumed all the sales, pop media, everything I could find about you into a prompt and I had to prepare me a preparation guide. Uh, and in the half hour, 45 minutes I felt pretty well prepared for this. So that's a, that's something anybody can do. You know, if you say preparing for a sales meeting.
John Golden: No, absolutely. And I think that's it. I think that's a great piece of advice is just start simple. But tell me just from a, from a, you know, as you're um, as you're a Chief Revenue officer, what is AI going to do to sales and who are the salespeople who are going to excel?
Glenn Fleischman: Yeah, that's a great question.
John Golden: So um,
Glenn Fleischman: AI is already helping um, just about every corner of what we do from sales enablement, uh, to uh, doing some of the grunt work and the more task oriented stuff around um, outbound and around inbound, messaging and prospecting. It's um, you know, we're in the process. It hasn't, we haven't felt the positive impact in it yet. But one of the most painful parts of the sales process in my world is pricing. Pricing has to be very complicated in what we do and very manual. Um, we're building agents to be able to really take all the human out of that and to be able to effectively input into a screen a couple of data points and get back um, a really accurate price proposal, customer facing price proposal quickly. So um, all those kind of things are really like either here or you know, days or weeks away.
John Golden: Mhm. So, so there's a lot of things that can come and help like make things faster, automate, take away rote and routine Tasks and all of that, what then does the sales per. Because you know, if, if that's, if your job is to say if you're a salesperson, if you're very task driven and everything and less strategic, you're going to have a few issues in the future because the tasks are going to be automated. Um, what kind of salesperson is really going to excel?
Glenn Fleischman: Yeah, the truth is in enterprise sales, right, it's not the task folks that are generally the ones that are excellent. It's the ones who do great discovery, who consistently apply a discovery framework like, I know spin is big for you. For me, I'm a med pick guy. Um, it's the ones who have uh, empathy, bring empathy into their sales conversations, can know how to read the room, know how to react, know how to handle objections, know how to um, you know how to find additional stakeholders. None of those skills are going away. So uh, and I don't see AI doing any of that in enterprise sales where I live. You know, maybe uh, on, you know, SMB type, really transactional sales, uh, AI will play a bigger role. But you know, I don't, I don't see the enterprise sales rep completely going away anytime soon.
John Golden: No, no, I would, we would agree with you. We think, um, in fact, I think this should really elevate the best of those type of salespeople. Uh, because you know, as you said, it takes all the other stuff away. It allows them to be more creative, build a relationship, all of that, you know, be more informed when they're having conversations. And so that I think it's going to absolutely, uh, elevate those people who, who sell that way anyway.
Glenn Fleischman: Uh, and think about it. Every single technology shift we've experienced has made sales reps basically have bigger quotas, be able to handle bigger quotas and be able to do more. I mean, you know, when I started there was no CRM. I had index cards with leads on each one, you know, and how to do an hour or two of desk research, meaning go to the library to do research. So I mean every technology shift has made us greatly more efficient and I don't see this to be any different.
John Golden: Yeah. Ah. And would you do, you know, market research and you know, consumer insights and all of those have been, they've been pretty manual in the past. Right. And also a lot of human interpretation. How does that work now with AI so that you still get the best, you know, you get, you get the information but you still get the human, uh, you still get the human nuance to it.
Glenn Fleischman: Yeah, that's such a great question. So um, you know, market research and insights were traditionally handled in an agency manner where you had expensive humans working on a project together with their customers. Over the last 10 years it's become um, there's a major piece of it and certainly where we play is something called the DIY era where there are platforms of researchers to be able to actually run the research and connect to their panels. We are bringing in the next era which we are calling aiy. And that is where um, the market research and the consumer insights, uh, expertise is built into the platform. So anyone, um, in brand or in strategy or in marketing, um, can get on a platform and not have to have a master's degree from a consumer insights program and be able to run world class research. So you know, having that, having that, that expertise built in to get through all the heavy statistics and the other things that um, you know, normally you, you know, needed a specialist person for. That's. Those walls are starting to break away.
John Golden: Yeah. And then that leads it to the, the real experts can then like look at the data, look at all of this and interpret it in different ways. So again, it's, again it's a kind of an elevation, isn't it? Letting AI do the donkey work.
Glenn Fleischman: It's exactly. And by the way, I wouldn't even call this donkey work. I get your point and your point is exactly right. But what I would say is, you know, historically you speak to any data engineer and they'll tell you 90% of what they do is boring cleaning up of data. So 10% is the fun stuff of, you know, actually engineering data and doing analysis. It's going to be the same. Um, you'll be able to trade low value work for higher value work.
John Golden: So I mean you're kind of at the intersection of AI, consumer, you know, consumer insights and business strategy and all of that. Um, what's your um, what, how are you, what's your process like internally to keep, to get all of those working well together?
Glenn Fleischman: Yeah, it's uh, Well, I would say we've been experimenting and trying to. Not trying to. We've been, we've been leveraging AI since it became available to us over the last, let's say 12, 18 months in our company. In some ways with great success and in some ways, you know, we've made real mistakes and maybe I'll answer your question by sharing mistake a mistake we made which is, you know, which is maybe a learning experience for everyone. Um, our company is relatively new to outbound we were fortunate enough to get a lot of our demand through referrals and events and marketing content, organic, whatever. So we've only built an outbound motion in the last, uh, 12 months. And uh, you know, when we started saying, hey, let's supercharge our outbound with AI, let's, let's really turn it over to outbound and you know, get 10 reps for the price of two. 10 SDRs for the price of two. What we found was our motion wasn't really nailed down, our content wasn't great, it was underperforming outbound. And so of course when we tried to bring AI into it, we, we were just scaling, uh, underperforming motion. And what did we get, of course scaled under performance. So um, you know, that made us really look hard in the face and say, okay, if the human process isn't right, if you haven't nailed the motion with humans, then AI, maybe AI can help you nail that and get that right. But until you get that right, don't try to scale with AI.
John Golden: Yeah. And I think that is such an important thing is that because, well, there's a few things. Number one, if you want to bring AI into your company and your data isn't clear, clean, um, the AI and you're going to use AI with your own data, it's not going to be very successful. Right. Because your data isn't clean. So you got to have your data clean. The other thing that you said, and I think that's so important, especially because everybody's so gung ho on automation is, is look at the pro, as you said, look at the processes first as a human processes and see how, and examine them and see if they're actually efficient or, or are you actually going to, as you said, you're just going to automate crappy processes which you get automated crappy processes.
Glenn Fleischman: Yeah. And you can't underestimate your point about getting the data right. Because while AI is amazing and ingesting a lot of unstructured data and being able to bring sense of that. Again, I'll give you another example where we didn't get it right. Um, to, to my new business team's credit, they are really making an effort to um, connect and build long term relationships with their prospects and the people they're dealing with. One of the ways they do that is by doing a lot of communications and text.
John Golden: Mhm.
Glenn Fleischman: And those text communications were not making it into the deal flow. They weren't in our CRM, they weren't in our GONG review. So of course when you start relying on the AI and gong, um, to forecast what's going to close, what's not going to close, do deal reviews. It's got an incomplete picture because it's missing data. And so we really have to be really in the process of working to make sure we don't lose that relationship building of being able to use text as a comms channel with our customers, but getting it included in the data set that we're using to analyze deals.
John Golden: Mhm. Yeah, no, absolutely. And it's really, and it's really interesting in that way is that the people aren't paying enough attention to the quality of data in their company. And uh, that's it. I mean if you think about, you know, we've never been very good people, have always been, you know, there's duplicates in here, there's this in here, this incomplete. And the other challenge that you said is as well is that there's all these different types, there's all these different ways of communicating with customers and prospects now and we have to kind of capture them all.
Glenn Fleischman: Yeah. And we're pretty good. You know, we've got, we've got phone calls, we've got Zoom and teams calls, we've got LinkedIn messages. But we, you know, we were mixing good old text. Mhm.
John Golden: And, and the thing is about that is, I mean, as I said, because people have different ways of communicating so you know, you have to be able to communicate to them in those, in those different ways. Um, what is, what do you say for, you know, maybe people who are, who are, you know, more advanced in their careers. Right. You know, and they're going, wow, uh, that's all I need. Another wave of technology. What's your advice to them? To be able to navigate through this?
Glenn Fleischman: Yeah, I mean it's become a cliche at this point, but I really believe a lot of cliches are cliches because they're true.
John Golden: Um,
Glenn Fleischman: it's highly unlikely in our world, enterprise sales, you're going to lose your job to an agent. M. You could lose your job to someone who's more effective at using AI than you.
John Golden: Yeah, absolutely.
Glenn Fleischman: So lean into the change. Um, you know, bite, eat the elephant. Bite. Bite. Bite by bite. Even, even little bits of, you know, you don't necessarily have to vibe code the most amazing agent, but you know, if you can learn how to prompt engineer well and write, write an effective prompt and get results that save you 15, 20 minutes, 30 minutes, an hour a day, um, you know, you're right in the middle of the pack. You're making progress, you're keeping up.
John Golden: Yeah, and the other thing too is, is uh, yeah. And the other thing too is, is um, is learning how to communicate with AI because when you do and you start to communicate with it like it's like it's somebody there to help you. Like it's. I mean I always think of it like my eyes, like I've got a bunch of PhDs who have 30 years business to help me whenever I want. And I think that's when people start to look at it that way. It becomes again, you can almost develop a relationship with your AI because if you get into that conversational mode it gets so much deeper, faster.
Glenn Fleischman: Uh, that's one half the equation. The other half of the equation is it gets to. The more you use it, the more it gets to know you that that context and knowledge persists. So the hundredth answer it gives you, um, is so much better than the first answer it gives you. And everyone's, everyone's got that first ChatGPT experience right where they gave a one sentence prompting got, you know, AI slop as an answer. You, you can get better at not getting AI slot.
John Golden: Absolutely. And in fact if you do it long enough, I have some of mine, like with Claude, where sometimes it'll actually remind me that I said something different.
Glenn Fleischman: Yeah.
John Golden: To say this is in conflict with what you said before about blah blah, blah. And I'm like okay, nice one, nice catch.
Glenn Fleischman: But. Right. That's the human condition. Our opinions change day to day and conflict day to day. And it's, and it's totally okay.
John Golden: Yeah. But like you're right though. I think that's. The people don't realize that the more you use, the more you converse with it, the more it learns about you and all of that, um, the better the answers you're going to get. And, and remember, just like you would if you were talking to another person is like you got. It's just like you would on a discovery call. You just don't take everything advice F. You go deeper, you, you validate, you know, you, you try to uncover what's behind behind that you can do the exact same thing in a, in a conversation with AI to get really good results.
Glenn Fleischman: Yeah. I mean I'm almost never using the first response it gives me when I give it a prompt. It's uh, it's in fact it's the iteration, the vibe coding of the answer after that first one is where really all the value comes in.
John Golden: Yeah, absolutely. So where do you see this going? I mean where do you see AI, particularly on the sales side? What do you think the future looks like?
Glenn Fleischman: I mean there's some obvious low hanging fruit, um, that I think are going to make humans more powerful. Um, and I'll try to, I'll push in the context of my situation, which is enterprise sales into a very complex vertical category where I mean the people we sell to are experts in market research in their domain. They know a lot. It's very hard for a salesperson to know as much as the person they're across the table from virtually. So, um, we've been building these things, I'm calling them sales caddies. Um, you can think of them as sales companions. For example, like all of our, in our platform, all of our AI functionality we called Skipper, um, we are, our platform does so much, it's very hard to keep that straight. And you know, in the past enablement, we would have done a big grand training and there would have been materials and various cloud drives and slack conversations that you would spend an hour to find. Now we've got a scpr, um, sales caddy, that's that, that for all each of our different Personas, what to talk about, how to sell it, how to describe it, what it does is right there side by side in your conversation. So you have it in context, in stride when you need it. And I think that's the future of sales enable and maybe the lowest hanging fruit and the thing you can do with the least amount of data connections and data cleaning pain that you know, we're probably all going through right now.
John Golden: And do you see any new, new roles or responsibilities emerging as well as, as AI becomes more embedded in sales?
Glenn Fleischman: Uh, I mean it's going to new roles. I say it a different way.
John Golden: Right?
Glenn Fleischman: There will be new roles, no doubt. Um, just, just as, you know, 20 years ago there was no such thing as a social media marketing manager and now that's, you know, one of the biggest jobs you can have in marketing. Um, uh, there will be new roles, but what I, what I can tell you was what I'm facing and what I'm doing right now is all my open roles are being rewritten for AI capabilities. I'm. You can't get a job in my organization without being able to show a portfolio of some things you've already done in AI. That's a mandatory prerequisite. It's in the job description. So um, you know, we're now rewriting all of our open roles not for what we need today, but for what that role is going to be in two years.
John Golden: And you know what I like about that, Glenn, is I think that's a great. That's a great thing for people to take away, is that that is going to be a requirement in the future. Let's face it. I mean, most salespeople, when you turn up for a job, it's, here's my track record, here's what I've sold, blah, blah, blah, good companies. Now you're talking differently. It's going, okay, that's all great. Now show me. We show me what you're. How you're leveraging AI to be even more effective. That's going to be a whole new frontier for many salespeople to suddenly realize they're going to get asked about their AI capabilities, not just their previous sales performance.
Glenn Fleischman: I've been talking. Anyone who finds this and does the research that's interviewing with us, you're going to get a little cheat code right now, which is great. But, um, you know, I've been talking with, um, one of my sales managers usually interview process. We give them a prompt and it's all. Sometimes it's a fake discovery call, it's a pitch or something like that, you know. Now we've been talking about changing that prompt to effectively giving them a situation. And do the desk research with me live in real time. Show me how you're going to do the desk research and uh, how you're going to, you know, in 10 minutes prepare for this call. You have, have they just came in inbound. And, um, that may be the new way we start testing people or one of the elements that we test for.
John Golden: Yeah, and I think that's a. I think that's a really clever idea actually to, you know, to see it live in real time. Because, let's face it, that's the thing that we've always struggled with, particularly when hiring salespeople is, is you kind of only have what you have to go on, their, their track record and what they do in interviews. You have really nothing else. Like, you know, we're all Other people have portfolio, you know, um, now being able to actually say, okay, let me see how you do this, how you do it efficiently. Let's go. That's. That's, uh, that is going to differentiate. And that's a great. So if you're out there watching as a salesperson now, you should start thinking about, you know, your. Maybe your next job or whatever, like, how can you show them that you're. You're the AI savvy person.
Glenn Fleischman: And this gets back to why you have to lean into it now and take little bites and get started. Because you know there is just absolutely no doubt in five years and almost no doubt in two years that it will be part of every job interview in enterprise and mid market sales. So um, yeah, now's the time.
John Golden: Fantastic. Well listen Glenn, thanks so much for all these great insights. Um, all of Glenn's information will be below this video. But before we go, please do remind people about you and what you do.
Glenn Fleischman: Uh, yeah, sure. Thank you. So um, I've spent my whole career in um, and telecommunications and SaaS, uh, and customer facing leadership, running sales and CS organizations typically in martech SaaS, marketing research SaaS. Um, our company does, as we said, is a consumer insights platform aimed at large enterprises and aimed at um, mostly B2C large enterprises in CPG, consumer, consumer tech, um, financial services, telecom, those kind of things. So um, I'm spending the rest of my career focused on um, transferring knowledge, mentoring, building skill sets, teaching people how to ethically succeed sales and uh, to build amazing long term relationships with customers because that's the only thing that really works.
John Golden: Yeah, fantastic. Well listen, thanks again Glenn. Thank you for watching and listening. See you all again very soon.
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